Pin
2-Day St. Michaels Itinerary
When is your trip?
Navigate forward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.
Navigate backward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.
Wanderlog staff
Updated • updatedAug 20, 2025
Updated • updatedAug 20, 2025
St. Michaels in 2 days
If you only have 2 days to spend in St. Michaels, we’ve narrowed down the top places you should check out to get the best experience of your time here.
With favorites like Harrison's Harbour Lights, Sail Selina II, and St Michaels Crab & Steak House, we’ll make sure you don’t miss out on all the must sees. We even included some of our favorite food spots around the area, like Justine's Ice Cream Parlour and Inn At Perry Cabin so you can get the best taste of St. Michaels while you’re here. To see our full list of food recommendations, check out our best restaurants post. If you're traveling on a budget, you can check out our cheap eats post.
Looking for other day-by-day itineraries in St. Michaels?
Visiting St. Michaels? See our St. Michaels Trip Planner.
Feel free to follow our itinerary exactly or tailor it to your own needs — happy wandering!
Your itinerary and your map in one view
No more switching between different apps, tabs, and tools to keep track of your travel plans.
What users say about the app
Table of contents
- St. Michaels in 2 days
- Most popular attractions
- Southeast side of town
Day 1
Most popular attractions
For day 1, we strategically grouped the most popular attraction, Chesapeake Bay Maritime Museum, with surrounding point of interests to start your trip off with a bang. Combining the average time spent at each location and traveling time in between, it should fill up about 8 hours of your day.
1
•SOPHIE J — Google reviewAlex N — Google reviewBeth K — Google reviewJohn W — Google reviewBarry A — Google reviewJessica H — Google reviewAnn O — Google review
Chesapeake Bay Maritime Museum
4.7
(1325)
4.6
(1069)
Maritime museum
Museums
History museum
Local history museum
Located in the picturesque town of St. Michaels, Chesapeake Bay Maritime Museum is an 18-acre waterfront venue that offers a deep dive into the bay and its people. Visitors can explore exhibits, take part in activities, and even enjoy boat rides. The museum's working shipyard showcases the region's maritime history, while a stroll along Talbot Street provides access to colorful shops selling everything from premium olive oil to crab-adorned T-shirts and hats.
We didn't know what to expect with this museum, but were really impressed by it! It is very well worth the visit, and there's more than enough to see in the 2 days the admission fee covers. At the beginning, someone went over the map with us, and explained some about the buildings. That was really helpful. It's not just a museum, but an entire complex of various buildings that are really each museums. I couldn't possibly do it justice by describing it- if you are considering going, you definitely should! I really enjoyed seeing the variety of boats, and the building that was built all around an oyster boat was probably my favorite. You could walk through it, hearing about it with the narration, and seeing all the different parts. There were fun facts about oysters all around, as well as a complete history of the oyster business in the area, canning, and even oyster wars! The lighthouse was pretty interesting, and showed all of the keeper's quarters set up, as well as some information about the various keepers, and a big map of all the area lighthouses. There was a whole building that showed about the blue crab, and the crab picking industry. There was a building that had lots of history and information about people enjoying the water in various ways over the years. As you walk around, the view of the harbor and the water is beautiful as well. The museum store is beautifully arranged, and contains a great variety of souvenirs and items having to do with the water.
Deborah M — Google review
I absolutely love the Maritime Museum on a visit to St. Michaels. Great staff, great price, wonderful views of the bay. So much history for all the family to enjoy!
The newly renovated entrance is beautiful! We haven’t been in probably a decade, but it’s very well done and there is lots to see. Kids had a great time. Views are stunning.
Beautiful museum and campus of buildings make up the museum property. We did the patriot boat tour and museum combo. The boat tour is listed as a 70 min narrated historical tour, but it’s more commentary than history. It was a great time and the different buildings at the museum cater to all ages. There is not much to do in St Michael’s other than eat, shopping and boating, so happy we went.
We had heard this museum was a must see and it didn't disappoint.
One fee for a two-day ticket that was not expensive. There is a lot of area to cover, so it was nice to know we could come back. We visited in October so it was not crowded.
We spoke with a very friendly painter who had been working on one of the boat and he told us a bit more about the place.
Plenty of self-guided areas and exhibits.
We enjoyed the ship building work - it was interesting to see the process step as well as the volume of lumber stocked and waiting to be used.
Beautiful views from the lighthouse.
I enjoyed walking among and reading about the exhibit boats they had on display, each with a detailed history of ownership and uses over time. Amazing.
The collection of outboards showed the changes over time - I can't imaging heading out into the sea with one of those old-timers even when it was brand new.
Definitely worth the time and money.
I really enjoyed this museum and its emphasis on local maritime heritage - crabbing, oyster catching and boat building. I spent a couple of hours wandering around the various buildings and learned a lot.
We had a tour of the CBMM. All of the staff were accommodating, well knowledgeable of their surrounding area and its history. They're volunteers who made all of my passengers feel welcome.
My sister & I celebrated our b
Day's &took a day cruise from Annapolis to St.Michael's!
213 N Talbot St, St Michaels, MD 21663, USA•
8 min · 0.44 mi
2•Lindsey M — Google reviewShanon J — Google reviewNatalie M — Google reviewMARY L — Google reviewMichael J — Google reviewRodney R — Google reviewKrystyna M — Google review
Ruse
4.8
(250)
4.7
(22)
Restaurant
Bar
Cocktail bar
Oyster bar restaurant
Seafood restaurant
Nestled within the trendy Wildset Hotel, Ruse is a delightful dining spot in St. Michaels that pays homage to a clever historical tale of local heroism. This restaurant not only serves as a cozy gathering place for both hotel guests and locals but also showcases an enticing menu focused on the flavors of Chesapeake Bay. Seafood lovers will be thrilled by the extensive selection of oysters sourced from various locations along the East Coast, making it a must-visit for anyone looking to indulge in fresh coastal cuisine.
A Delightful Dining Experience at Ruse in St. Michaels, MD
Ruse in St. Michaels is an absolute gem. From the moment you step inside, the ambiance is stunning—both the indoor and outdoor spaces are beautifully designed, making for an inviting and memorable dining experience.
The service was impeccable, with the wait staff being exceptionally courteous and helpful. Our server, Brittany, was beyond amazing. She made our experience even more enjoyable and is one of the main reasons we’d return and recommend Ruse to our friends.
As for the drinks, the mocktails were outstanding—citrusy, refreshing, and thoughtfully crafted. They were the perfect complement to the meal.
The raw Wellfleet oysters were a standout—meaty with an intense brine flavor that was absolutely fantastic. The Roasted Wild Diver oysters were also very good, though I do hope the restaurant recycles the rock salt they’re served on, as otherwise, it seems like a bit of a waste.
The Apple and Endive salad was a highlight—so fresh and well-balanced that I wish I could find it closer to home. The steak tartare was another winner, offering a complex and well-portioned dish that impressed with every bite.
The only dish that didn’t quite resonate with me was the Chicken Liver & Foie Gras Parfait. It had a PB&J-like quality with a chickeny flavor, which I’m sure many would enjoy, but as a foie gras purist, it wasn’t my personal favorite. However, the Porcini Mushroom Lasagna more than made up for it—rich, flavorful, and an absolute must-try for mushroom lovers.
Overall, Ruse delivers an incredible dining experience with top-notch service, beautifully prepared dishes, and a welcoming atmosphere. We’ll absolutely be back!
Norwin P — Google review
WOW! What a place! My family dined here while we were on vacation in August and I have to say we had the best experience. The wait staff were very attentive and helpful. But the food absolutely stole the show. Incredibly delicious. Plus happy hour pricing was very good!
We had an incredible dining experience at Ruse in St. Michael’s! Brittini was our waitress and she made the evening exceptional—her enthusiasm and rave reviews about the menu helped us make some fantastic choices. We ordered the lamb shoulder and the lasagna, along with the trout dip and carrots, and every dish was absolutely delicious.
A big shoutout to Tanner as well, who did an excellent job pairing our wine perfectly with our meal. The combination of top-notch service, amazing food, and thoughtful wine recommendations made for an unforgettable night. Highly recommend Ruse if you’re in the area!
Shanon & Jeremy Johnson, Journey Home Realty, LLC | eXp Realty
Awesome spot. Went for my husband’s birthday and they gave us a free glass of wine. The raw bar was awesome we loved the scallop crudo and the oysters. We also got the crab pasta, cucumber salad, and pork chop— all delicious.
Wow!!! My experiences today prompted me to write this review. We are staying at Wildset for our babymoon and read about how Ruse is the best restaurant in St. Michael’s. We tried the happy hour first and sat at the raw bar- the roasted oysters and spring gem salad were delicious and this was some of the the best service I have ever received from a server while sitting at the bar!
We then went later that day to try dinner and we were in for a treat! The lamb ribs, wild mushrooms, and smoked trout were all so delicious. The trout in particular was cooked to perfection, crispy skin on the outside, tender meat inside, and the lemon caper sauce was delicious. I also loved the labneh ice cream, perfect amount of tangy and sweet with the rhubarb compote and crumbles. Brittany, our server, was so genuine and pleasant to be around, and enthusiastic about all of our choices. She gave us amazing service and was so sweet to even gave us complimentary non-alcoholic sparkling rose to congratulate us! My God, can’t wait to come back to try the famous burger and shoestring fries!
Possibly my favorite dining experience in St. Michael’s, it’s a toss up with Bistro St. Michael’s. Love the modern dining room, the service was knowledgeable and attentive, and the food was delicious!!
Tried the Speedo cocktail which was well balanced and not overly sweet. For my main, got the Blue Crab Cacio e Pepe which was phenomenal.
Would def recommend and would return!
We had a delicious meal celebrate our anniversary. Caleb took excellent care of us, the Speedo and I Like It When You Call Me… were delicious cocktails. The food was fantastic, and well portioned. We especially loved the short rib and the shrimp aguadulce tostada. The fried corn ribs were amazing, a must try.
A really great experience overall! We tried several dishes. The hummus and the blue crab cacio e Pepe were favorites! Really enjoyed the cucumber salad as well. The cocktails were solid and the ambience was comfortable and casually elegant. Also appreciated the very reasonable noise level/comfortable level of music playing without being intrusive. I’d recommend Ruse to anyone visiting St. Michael’s!
209 N Talbot St, St Michaels, MD 21663, USA•
Need a place to stay?
Where
When
Navigate forward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.
Navigate backward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.
When
Navigate forward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.
Navigate backward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.
When
Navigate forward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.
Navigate backward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.
Travelers
2
Travelers
2
5 min · 0.28 mi
3Verena A — Google reviewAustin G — Google reviewKevin B — Google reviewKing J — Google reviewE.B. N — Google reviewCorey S — Google reviewDen — Google review
Patriot Cruises
4.7
(272)
Boat tour agency
Historical landmark
Embark on a relaxing cruise down the Miles River with Patriot Cruises and explore the charming town of St. Michaels on Maryland's Eastern Shore. During the 75-minute scenic tour, guests can admire stunning 200-year-old mansions and even visit filming locations from 'Wedding Crashers.' The knowledgeable captain shares captivating stories about the area's history, including tales of the Chesapeake Bay watershed and the Battle of 1812.
Reasonable price for an hour and 10 minute cruise on the Miles river. Historic mansions and homes. Some war of 1812 history. Beautiful views of nature and birds. Friendly, professional staff. Bar on board where you can get both alcoholic and non alcoholic beverages plus snacks.
Thomas Q — Google review
Found this attraction advertised on a flyer at my resort, miles away! Decided to come and enjoy a guided tour on a very expansive waterway. Not much action (very few boats on the water), but hints that whales and dolphins had been spotted over the years. Very limited snacks so don’t board if you’re hungry! Indoor (air conditioned) and fresh air seating. Your goes rain or shine, clouds made this trip not as stifling. Family friendly and dog-friendly!
If you enjoy a relaxing boat ride, Patriot Cruises is for you! One a two-level boat that looks like a historic ferry, the cruise is 70 minutes and includes a tour pointing out historic sites and beautiful waterfront mansions. The final 20 minutes includes music and relaxation. There's a bar and snack area in the lower level and enclosed seating with tables. Upstairs is open air seating. To see most of the properties noted, sit on the right side of the boat. Bring cash so you can tip at the end.
I run a Photo Booth company and worked with patriot cruises to coordinate a Photo Booth for a wedding cruise over Memorial Day weekend. All staff were super courteous and helpful, even offering to help me carry to gear on and off the ship.
I worked with Joyce who was awesome and knowledgeable and really helpful in pinning down logistics in a challenging situation on a holiday weekend no less!
Highly recommended if you want a great evening with an experienced and helpful crew. You’re in good hands.
I was told I was the first Photo Booth to be aboard the ship, I hope it’s not my last time!
Thanks Joyce and everyone at Patriot cruises!
My wife and I did the island music cocktail cruise which was amazing! Captain Matt and crew were phenomenal! Nice smooth cruise with great music and stunning views. Definitely recommend checking it out if you're in the St Michael's area.
Price is very reasonable. Crew is friendly and helpful. Boat has two seating options (below in covered area and above with open air and views). Bar/snack area is great; drinks are good and inexpensive! Trip was about 75 min and included a history tour. Boat ride was smooth. Overall, a great way to enjoy the Chesapeake.
Absolutely incredible.
We had our wedding on the Patriot. Joyce is the absolute best! She is so easy to work with, great communicator, so helpful and full of ideas. Captain Matt and Crew are so pleasant and great to work with as well.
Truly cannot say enough great things about the entire operation. The cruise was perfect, the boat was clean. Everyone enjoyed their time!
Highly recommend this excursion...its chill, informative and a great way to spend a little over an hour on the water.
Park at the, Chesapeake Bay Maritime Museum, 213 N Talbot St, St Michaels, MD 21663, USA•
< 1 min · 100 ft
4•Mike M — Google reviewKaren K — Google reviewRachel R — Google reviewKathleen M — Google reviewP — Google reviewParigino48 — Google reviewIan L — Google review
The Crab Claw
3.9
(1135)
3.6
(1207)
expensive
Seafood restaurant
The Crab Claw is a casual landmark crab shack located on Burns Street, offering regional seafood and outdoor dining with views of the Miles River. It was established in 1965 by a local couple and remains family-owned to this day. The restaurant's seaside location provides beautiful waterfront views, making it a popular choice for those seeking a scenic dining experience in St. Michaels.
All food was good but Crap Dip it’s a must!! Loved the Crap Cake and hush puppies. The place is not beautiful but has an old school-small town charm. I can live with the level of the service.
Jose C — Google review
Awesome atmosphere right on the water in St Michael’s but unfortunately that’s where it ends. It is very expensive for the frozen food that is prepared. Burger was tiny so wouldn’t recommend that and the salmon was very small and didn’t have a good taste. The fried crab ball was pretty good but again not worth the $30.
While visiting St. Michael's you have to experience seaside dining at the Crab Claw restaurant. It's an experience to see all the beautiful yachts and boats come and go. A family of ducks paddle by and of course there are blue fin 🦀 crabs. You can order a single one or by the dozen.
We sat right on the water outside and watched the boats coming in and out. We happened to be there at the same time as the entire Terps coaching staff so that was cool. They had some pretty boats! The crab dip was really good and came in a yummy sourdough bread bowl. Most patrons were there for the crabs, tables were all dressed in crab paper and the bucket of hammers and paper towels were atop. Drinks were good. Atmosphere was fun!
We ordered hard crabs. The biggest they had were large. All were almost entirely devoid of crabmeat. No backfin lump. Just a few shreds of crabmeat. I complained to the waitress and showed her an empty shell. She took it to the manager and they gave us half off. What we got wasn’t even worth that. The picture shows the backfin area just after opening it. Empty!
Worst experience ever!!! DON'T GO HERE!! This place needs a major staff change and management change. The way they run their restaurant is not good at all. There were tons of servers yesterday just standing around. Why did it take over 20 minutes for someone to wait on our party. We had to get someone's attention to let them know hello we are here to eat and we would like to place are order with you. The outside bartender was rude and the guy waiter we had was rude as well. He was more focused on helping the larger party towards the back of the deck then helping us. He stopped mid way while taking our order to help run food to them. Isn't that a job for the food runners at a restaurant not the waiters job. ALSO THIS WAS MY MOM'S FIRST TIME COMING HERE AND MY MOM SAID IT WILL BE HER LAST TIME EVER GOING THERE AGAIN!!!! SHE SAID ONE AND DONE!! NEVER EVER AGAIN!! It's so sad because she was looking forward to enjoying the water views and having some yummy crabcakes. Well the unfortunate thing is know one in our party received our lunch yesterday. It took so long just to get the appetizers it was really ridiculous!!!! We sat there well over 1 hour and still no lunch in sight. However the tables next to us who sat down a good while after us received their food. Does that make any sense at all? NOPE!! There was a guy server vaping near the soda area. Not professional at all and super grose too!! This restaurant used to be so good back in the day not anymore. Very sad and disappointing to say the least!!! PLEASE SAVE YOURSELF THE TIME AND ENGERY AND GO SOMEWHERE ELSE WHO WILL MAKE YOUR DINNING EXPERIENCE WONDERFUL!!!!!
My wife and I ate lunch here on 10/15/25 and swore “never again.” The crab cake that I ordered was tasteless and “off” and *very* expensive at $36. It was accompanied by a baked potato that was just meh and applesauce that obviously had been spooned out of a supermarket-bought jar. The only tasty and satisfying part of the entire meal was the Smith Island cake that, by the waitress’s own admission, had been bought from a commercial bakery. My wife’s feelings about her order of crabmeat sandwich and french fries were pretty much the same as mine about my order. Worse, we were both quite ill later that afternoon and evening with various unpleasant stomach and intestinal symptoms. We also didn’t enjoy the seating on hard campground-style benches. The next day, 10/16/25, we stopped for a seafood lunch at the Fisherman’s Inn at Grasonville in Kent Narrows, one of our favorite restaurants, and as always had a delicious seafood meal there. The crab cake my wife ate there was far, far superior to the Crab Claw’s, and was much cheaper at $23 than the Crab Claw’s ($36). My dish of broiled flounder in lemon-and-chive beurre blanc was outstanding, and the Fisherman’s Inn’s delicious applesauce is home-made. The Fisherman’s Inn also boasts a very comfortable and pleasant dining room, unlike the Crab Claw’s uncomfortable open-air shed. Avoid the Crab Claw in St Michael’s like the plague !!!
Atmosphere is nice by the water. Food is alright and service was great to start; but as it got more crowded, it was tough for the servers to cover all the tables.
All in all, a good spot if you’re more focused on the vibes
304 Burns St, St Michaels, MD 21663, USA•
Create your ultimate travel itinerary
Plan your itinerary, find lodging, and import reservations — all in one app.
Where to eat
When you need a food break from visiting all the attractions today, these fan favorite restaurants are about a 1-minute walk away from Ruse.
Justine's Ice Cream Parlour
4.7
(348)
4.5
(501)
cheap
Ice cream shop
Dessert shop
Justine's Ice Cream Parlour is a delightful, nostalgic spot that transports you back in time while satisfying your sweet tooth. Nestled on Maryland's Eastern Shore, this charming parlor boasts an extensive menu featuring over 42 premium flavors of hand-dipped ice cream, soft-serve options, and even non-dairy sorbets. Since its establishment in 1987, Justine's has become a beloved local favorite for both residents and visitors alike.
Loved this place. Located in the heart of St. Michael's.
Went there for an ice-cream and got a great experience.
From the posters inside to the full story of Justine's ice-cream directly from the owner. So many flavors and all of them so delicious.
Maria P — Google review
Been coming here for a couple years. My husband always gets a hot fudge sundae. The last two times the sundae has been very small with very little whipped cream and hot fudge. We will not be getting another, miss what it used to be and the price isn't cheaper for the cheaper product
Delicious ice cream shoppe in a quaint, charming town! Caramel cold brew and cookies & cream flavors were amazing! Within walking distances from several restaurants and cute stores.
Vintage icecream shop with yummy flavors! We ate too fast and forgot to take photos of the icecream 🍦 Maybe next time.
My wife and I were looking forward to this place all weekend while we were in town, and it didn't disappoint! We both ordered shakes, the German Chocolate and the Chocolate-Covered Marzipan shakes. Although they both sort of look the same in the pictures, they were delicious and unique. The German chocolate one had a lot of coconut in it and a whipped cream topping. The Marzipan shake had a great Marzipan flavor. It was nice to see the workers were both wearing masks! Definitely a good dessert shop!
Great customer service! Delicious ice cream!
Justine’s is awesome! We got the brownie sundae with mint chocolate chip and the single scoops were huge; you definitely get your moneys worth. The overall taste was absolutely delicious, I wish I could try everything on the menu. Would definitely recommend and go back!
A delightful little ice creamery! Lots of flavors and suggested combinations, and an ice cream challenge! They have a ton of shake and float options as well, and plenty of seating if you want to just chill out, though their cones are perfect for waking. The peanut ripple ice cream is just perfect, and they come up with unique combos too!
106 N Talbot St, St Michaels, MD 21663, USA•
Inn At Perry Cabin
4.5
(432)
Hotel
Resort hotel
Nestled in a private corner of the Chesapeake Bay, the Inn At Perry Cabin is a 19th-century manor house offering elegant rooms and suites, a spa, al fresco dining, and event space. It is the only Forbes-rated destination on the Eastern Shore. Guests can enjoy various activities such as sailing with Captain Conner, exquisite meals at STARS restaurant, knot tying lessons from Mike, spa treatments by Sara, and attentive service from staff like Shawn and Heather.
On a whim, my wife and I visited the Inn for the first time for lunch. Had a wonderful time. The food, the service, and the setting were terrific. Highly recommend the deviled eggs; you've never had them like this. My wife had the cream of crab soup, the best she's ever tasted. And I had the salmon. Not something I usually order, but I'm glad I did. It was delicious.
Mike E — Google review
This property is magical! We had the most lovely time visiting. Our lunch was spectacular! Johnathan, our server was so personable and helpful with any questions we had. He described the amazing private dining experiences we can book with a tasting menu and wine pairings… we will definitely be booking a long weekend here again with friends! 10/10 recommend
Jonathan was outstanding – incredibly friendly, attentive, and diligent. He not only took care of us but also made sure our two little puppies felt welcome, which made the experience truly special! Puppy menu is so cute 😻😻
Kai was incredibly helpful and courteous. He assisted us with docking our boat and made sure it was well taken care of while we enjoyed lunch and dinner at the restaurant. His service made our visit stress-free and enjoyable
A True Gem in Every Season
The Inn at Perry Cabin has always been one of our happy places, and this recent stay reminded us exactly why. From the moment we arrived, every member of the team—from the valet, concierge, to the housekeeping and grounds crew—was incredibly warm, professional, and attentive. The staff goes above and beyond to make you feel at home, and it really shows in the little things.
We accidentally checked out without settling our bill, and Mason was fantastic in helping us get everything squared away quickly and kindly—true five-star service.
The rooms and resort amenities are luxurious, and having an outdoor space made it even more special. We loved waking up to the sounds of birds with the doors open—an experience that made us feel totally at peace. Springtime here is breathtaking with all the flowers in bloom, but honestly, this place is stunning no matter the season.
Whether it’s your first visit or your tenth, the Inn at Perry Cabin is a place where you can truly unwind, reset, and soak in the beauty of St Michaels.
Received very disappointing service. I went sailing and ordered a fruit platter. It is my personal belief that if you are charging delivery fee and including gratuity, you owe it to your customers to provide top-notch service rather than the multi fruit that I received. When I reach out via email with photos of the mold on the fruit which was sitting at the top, I was prompted to provide my telephone number, which in an office itself proves a level of inattentiveness as my name and all other details related to my reservation were included within that email. Nonetheless, I provided my phone number and never heard anything back other than a “Thank you for confirming.” For the last few years, I have gone sailing at Perry cabin at least once or twice a year And have returned only because of the level of service however, if this is how things are or can be, no thanks.
Not worth the cost in my opinion. My husband and I traveled to the Inn at Perry Cabin in May for our honeymoon. Candidly, would not do it again. We arrived to our “waterfront” room (which we paid extra for) and there’s a massive tree blocking any view of the water, our shower was broken, our toilet was broken. My husband asked the front desk if we could have a bottle of champagne or something as it was our honeymoon, they told us to order room service. I’ve stayed at locations with much nicer amenities for much less $$. Daniel in guest services is probably the only reason we stayed - he did his best to make it right. The golf course is lovely and we really enjoyed our sailing trip. However, the bartenders at the hotel bar are not personable and trash talked other guests the whole time. It did not exude hospitable vibes whatsoever. In hindsight we wish we’d stayed at a local bed and breakfast. St. Michaels is lovely, but this establishment did not meet our expectations.
We celebrated an important anniversary at the Inn at Perry Cabin in June, 2025. The Inn is a lovely property, beautifully landscaped and situated on the Miles River, which provides serene nautical views. We found everything to be 5-star quality at the Inn, and we would single out the extraordinary staff. To a person, they worked to make sure we enjoyed our visit. Our room was superb, beautifully furnished and very well-appointed. We look forward to a return.
We did not stay at the resort, however went there for lunch and just a stroll around the property.
The resort was beautiful, well manicured, but a lot smaller in person.
Food - very disappointed. The food took 45 minutes for hamburgers and bisque soup.
Second, The hamburger meat was beyond well done, the bun was charred black, and the soup was cold ! If you can’t get hamburgers and soup right, I’m afraid to try everything else.
Needless to say, it was bad enough where I had to voice my opinion and get comped for the entire meal!
I would give this place a solid 2.0.
308 Watkins Ln, St Michaels, MD 21663, USA•
Need a place to stay?
Where
When
Navigate forward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.
Navigate backward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.
When
Navigate forward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.
Navigate backward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.
When
Navigate forward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.
Navigate backward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.
Travelers
2
Travelers
2
St Michaels Crab & Steak House
4.3
(530)
Permanently Closed
affordable
Steak house
Restaurant
St. Michaels Crab & Steak House is a casual eatery located in an 1830s oyster shed on a marina, offering local crabs and American cuisine. It's the perfect place to unwind after a busy day, with outdoor waterfront seating providing stunning views of the evening sunset and fresh Maryland seafood. Visitors praise the courteous staff, delicious food, and nautical ambiance.
October 2019 - found this place after the first restaurant didn't have any steamed crabs. It turned out to be a hidden gem. The place is on the water, you have the option to eat inside or outside and inside there are a some locations with different views. Staff was super courteous and friendly - very welcoming place to eat. The food is DELICIOUS! The crabs were steamed to perfection. I am really looking forward to visiting when the weather is better!
Shalonda L — Google review
Popped in for an early dinner and had the NY Strip Steak with a baked potatoe and a ceasar salad. The food was prepared well and was average on presentation and taste. The server was friendly and kept checking on us throughout our dining experience. The bar area takes you back a few years but the beer is good and cold.
If you are looking for waterfront dining at a popular spot with views of boats, no better place than having dinner in a marina. We had our dog with us, so we were welcomed to the patio.
The service was fast and efficient, and our seafood was also delivered quickly. It was very good, better than I expected on a busy holiday weekend. For pure nautical ambience, I will definitely come back.
Imagine a bar where sailors go to grab a beer, eat some crabs and share tales of the sea... you're likely imagining St. Michael's Crab and Steak. The chef is clearly capable; but this is the type of place where one expects to see a pirate... its pretty cool
Also, their sweet potato fries are on point!
Overall it was just an OK experience at St. Michael's Crab & Strakhouse. To start, I must say that the service was phenomenal. Our server was very friendly and helpful; she might be the only reason I'd consider giving it another try. To begin the meal, the cream of crab soup was very disappointing. It had the consistency and texture of yogurt and wasn't particularly flavorful. The steamed shrimp was fine and the Rockfish was quite tasty. Similar to the soup, my coleslaw side had an odd, thick yogurt-like texture without much seasoning. I may come back to give other parts of the menu a try but I'm not in any hurry.
The staff is incredible here! As out of towners they were happy to answer our questions and give us other great recommendations for other places to eat and adventure to. The food was good but not the best around but definitely a great place to stop by and get a drink and enjoy the local scenery!
Staff was friendly and helpful, Food was good, portions could be bigger. Prices are a bit high.
We caught them at the end of the evening on a Sunday night but we were not rushed and the view was lovely. I went with the fried clams and the hubby got chicken. Everything was very good.
305 Mulberry St, St Michaels, MD 21663, USA•
Bistro St. Michaels
4.7
(349)
4.5
(686)
expensive
Bistro
Bistro St. Michaels is a charming New American restaurant located in the historic town of St. Michaels, MD. The restaurant offers a romantic setting and a market-fresh menu with gluten-free options, making it an ideal choice for a special dining experience. With picturesque views of the harbor, Harbour Lights provides an unforgettable dining atmosphere.
We had the pleasure of dining at Bistro St. Michaels during our stay at The Oaks, and it was one of the highlights of our trip. From the moment we arrived, we were charmed by the restaurant's inviting atmosphere.
Every dish was delicious and the service was fantastic. The shrimp and grits were perfectly executed - rich, creamy, and bursting with flavor. The fried green tomatoes topped with fresh crab were beautifully crisp with a delicate sweetness that complemented the crab beautifully.
For our mains, their famous braised beef short rib was absolutely sublime - fork-tender with deep, complex flavors and gorgeous presentation. The pan-seared tilefish with red quinoa and broccolini highlighted how fresh and simple ingredients can really shine.
We couldn't resist ending with the bread pudding à la mode, and we're so glad we did. Warm, indulgent, and drizzled with butterscotch sauce, it was the perfect finale to an outstanding meal.
Bistro St. Michaels truly captures the essence of exceptional Eastern Shore dining with fresh ingredients, thoughtful preparation, and warm hospitality. We can't wait to return on our next visit to the area. Highly recommended!
Better L — Google review
Excellent dining ! Food and service were amazing. Food with great finesse and taste and service also with a heart. The meat platter was amazing! And their breadpudding with homemade butterscotch was so irresistible that I had no time to make a picture ;-).
The atmosphere is really nice and cosy. We will come back!
First visit and would def return!! Staff and waitress were all super nice. Space is very inviting. Lastly, food and drinks were terrific!!
I was still a little full from a heavy lunch but ate every drop of my gumbo cause it was that good! Partner got the crab cakes which she also enjoyed. Dessert was a nice highland scotch for me(Oban) and the strawberry panna cotta for her.
On a scale of 💯, I give them 110!
The bread pudding was so good.
I had two other dishes, the shrimp and grits and the bone marrow. I really enjoyed them but once I had the bread pudding, it was incomparable. It was so unbelievably good.... I can't say enough about the texture, flavor, density of the bread pudding. It was so out of control delicious. Good portion size as well. I am so happy I decided to stop in.
It was our 3rd time visiting the area from Long Island. Each time, we stop here for dinner. The staff is kind and attentive. The atmosphere is cozy and the food is delicious.
We come from an area with a lot of great restaurants and the Bistro ranks among the very top in comparison.
Our server Christian was excellent!
He’s very knowledgeable about the menu and able to help us make the perfect choices for our wine /meal.
I would definitely recommend this place.
p. s. They have a really nice outdoor space to enjoy ur meal out back.
Went for happy hour. Had the rose (dry and lovely), the moules & frites (excellent), and off the standard menu, the cream of crab soup (tasty with a not too thick consistency). Sat at the bar that looks into the kitchen which was entertaining. Excited to go back!
If you have ever read Elain Hildabrant The Blue Bistro you will love the menu options and how this restaurant runs.
We sat at the bar and watched to open kitchen.
Easily the best meal I've had in St. Michaels was here. I highly recommend sitting at the chef's counter--it really added to the experience. The staff was attentive, kind, and on point the entire evening.
We went with a few off-menu specials: fried green tomato appetizer, scallops with house-made pasta, and veal ribeye. Everything was cooked perfectly and full of flavor. Cocktails and appetizers were just as strong, unique and well-executed.
Doug and Jenn, the owners, made us feel genuinely welcome and gave great menu recommendations when we were unsure of what to have (everything sounded so delicious!!!) Our server Peter was extremely professional and on top of it the whole evening. Every staff member we met was super conversational, professional and friendly, and they made us feel welcomed.
I'll definitely be back every time I am in town!!! I'm already thinking about hosting a private event here. The outdoor patio space with bistro lights looked like a great setup for it, and I've got a birthday coming up. My local friends had raved about how lovely the ambiance, food, and service is and I’m so glad I checked it out! They’re consistent!!!
403 S Talbot St, St Michaels, MD 21663, USA•
Create your ultimate travel itinerary
Plan your itinerary, find lodging, and import reservations — all in one app.
Day 2
Southeast side of town
For day 2, we recommend exploring the southeast side side of town. Start the day off with Sail Selina II, then wind down and take it easy by the time you get to Classic Motor Museum of St. Michaels. All together, your day would be filled with about 8 hours of non-stop fun.
1Tiffany P — Google reviewRene T — Google reviewMichelle B — Google reviewJohn W — Google reviewMarianne G — Google reviewLisa H — Google reviewSuzanne R — Google review
Sail Selina II
5.0
(1292)
Boat tour agency
Boat rental service
Sightseeing tour agency
Wedding venue
Sail Selina II offers a unique experience for those looking to explore the waterfront. Visitors can rent kayaks or paddleboards from Shore Pedal & Paddle, take a sunset cruise on the sailboat, or go biking between St. Michaels and Tilghman Island. The boat sets sail from Knapps Narrows Marina on Tilghman Island and provides a smooth ride along the Chesapeake Bay.
Sailing with Captain Iris was one of the best parts of our trip to Saint Michaels. She is so knowledgeable and her knowledge of the history of the beautiful homes we sailed by was amazing. And to add to our adventure, Captain Iris saw a smaller sailboat in distress and with her expertise, Captain Iris was able to rescue the boater and tow him and his sailboat safely into the harbor. What an amazing experience and Captain Iris is one in 1 million. You would definitely enjoy a sale with her on the Selena II.
Diane P — Google review
My daughter and I absolutely LOVED our two hour sailboat ride aboard the Selina II and recommend it highly. Iris, our captain, and Matt were wonderful and engaged us in great conversation and imparted a wealth of knowledge about their unique boat, the beautiful area including it’s history, and all things nautical. I also enjoyed a delicious glass of champagne onboard. If you are traveling to St. Michaels, I highly recommend you book a trip on the Selina II. You will disembark feeling relaxed and refreshed and wanting to do it again the next time you visit! Thank you, Iris and Matt for an amazing adventure!
What a wonderful experience! Very intimate short trip, just 2 hours. Just six passengers with Captain Iris and first mate John. We were not experienced sailors and we were made to feel very comfortable while getting the real "on the water" vibe. Lovely early afternoon spin in the beautiful "Selena II" with some wine and lovely conversation. Highly recommend! Glad to be a tiny part of her 100 year journey. Would have done the evening sail but they were sold out. Charming.
My newlywed husband and I celebrated my 60th Birthday with a special trip upon the Selina II, and what a special trip it was. Captain Iris and her First Mate John were so very knowledgeable, not only about the Selina but about surrounding boats, breathtaking homes and famous Inn’s, and even the nautical history of the Chesapeake Bay area. We were there for an especially terrific sail as we joined a long boat canoe race that was taking place during our trip. It was surreal to be able to glide around the long boat as they struggled to catch the wind that day. It was truly magical and something we intend to repeat the next time we’re in the St. Michael’s area. We highly recommend you charter a trip with Captain Iris and the Selina II!
We are so grateful to have had the incredible opportunity to sail aboard Selina II with Captain Iris, crew, and other guests. This is an experience you don’t want to miss when visiting Saint Michael’s. This history of the vessel and family of stewards over the decades is nothing short of astounding. Make sure to take advantage of this opportunity before Selina II finds a new port of call. Captain Iris and her vessel are one of a kind. The experience will leave you with a smile every single time it crosses your mind.
We celebrated our anniversary with a Champagne Sunset Cruise aboard the Selina II - what a beautiful night. The sailboat is gorgeous and Captain Iris and the crew made every moment interesting. Great info about St. Michael’s, wonderful views and a joy to be on this beautiful vessel.
My husband and I sailed the Selina II on August 31st, and it was such a relaxing and fun trip. Captain Iris is a joy and so knowledgeable about the Chesapeak and St. Michaels. First mate Matt was great and engaging as well. Overall, it was a 10/10 experience, and I highly recommend it.
We had a wonderful time sailing aboard the Selina II on the Chesapeake. Selina is turning 100 soon so if you’ve been meaning to do this you definitely should. Capt Iris and her crew were great -very knowledgeable, attentive and fun. Champagne aboard was the perfect touch. We highly recommend this day excursion to appreciate St Michaels and our beautiful bay!
101 N Harbor Rd, St Michaels, MD 21663, USA•
13 min · 0.7 mi
2•Steve P — Google reviewBecky — Google reviewJohn W — Google reviewMichael A — Google reviewDavid L — Google reviewLily W — Google reviewLeslie J — Google review
Foxy's Harbor Grille
4.4
(1179)
4.0
(962)
affordable
Restaurant
Bar
Event venue
Wedding venue
Foxy's Harbor Grille is a popular riverside eatery in Saint Michaels, known for its relaxed beachy ambiance and delectable seafood offerings. Nestled near the harbor, it provides stunning water views, enhancing the dining experience. The menu boasts an array of seafood delights including crab cakes, shrimp, and fish prepared in various styles. With its charming waterfront setting and Key West vibe, it's a great spot to savor delicious dishes while watching boats sail by.
10 outta 10 great place to go for food, fun and friends. Great music! The food is amazing. Try the peanut butter pie😋🤤🤌 and enjoy the marina... In beautiful St. Michaels, MD. Staff are stellar as well. ✨🫶✨
Jen F — Google review
While I did enjoy the outdoor seating on plastic chairs, the food was just okay. Ordering was quick but the kitchen takes its sweet time delivering your meal. The guacamole on the nachos appeared tinted brownish instead of a nice bright green. So go there for the right reason, atmosphere, outdoor lively bar, view of the boats and water. In my opinion, order the tasty muscles, skip the nachos. Cheers!
Decided to visit St Michael’s for the day and decided to stop in for a quick bite and sip. The weather was gorgeous so there were lots of people out and about. Only waited 30 minutes for a table on a holiday weekend. Service was great. Ran into friends. Everyone was having a great time. Live music! One of the best crab pretzels I’ve had!
We stopped in for drinks about 2PM on Wednesday 10/15. Perfect weather for being outside in October! We were looking for a place for dinner later and the bar specials were perfect. When we came back at 4 and there were nice seats with a water view on the deck. We had two crab cake dinners at the best price in town. All lump crabmeat, asparagus and mashed potatoes very well plated. So good we ordered another to split.
Drafts were icy cold as well as the bottled beers. I also enjoyed a Mai Tai made with the local dark rum.
Place was pretty busy and only one waitress was working, but she had the place running smoothly.
On our list for a return visit.
Enjoyed a house peach margherita and a bowl of cream of crab soup tonight; a perfect light dinner to cap off a day of exploring St. Michael's for the first time. Reese picked up our table after we appeared to be overlooked for several minutes. After that we were in good hands. It was a beautiful, calm, quiet night on the river. Perfect for relaxing and enjoying the view.
Loved it! Really cool, welcoming place. Friendly people. Staff was helpful. Best crab pretzel crab 🦀 🥨 I've ever had!
Went there on a Sunday afternoon and there was live performance. The vibe is so chill just sitting next to the water with warm food and live music. I really recommend their crab mac chess bc they don’t skimpy on their crab. The oyster tastes fresh I wish they cleaned the outer shells as well bc I couldn’t slurp the oyster. Overall will come back!
This beautiful location in St Michaels was the perfect place to grab lunch. They are dog friendly on the patio so I was able to bring my dog. The food was special and the service excellent.
125 Mulberry St, St Michaels, MD 21663, USA•
Need a place to stay?
Where
When
Navigate forward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.
Navigate backward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.
When
Navigate forward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.
Navigate backward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.
When
Navigate forward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.
Navigate backward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.
Travelers
2
Travelers
2
8 min · 0.41 mi
3•Rick R — Google reviewTamara N — Google reviewNushrat H — Google reviewM B — Google reviewHéctor A — Google reviewAnn O — Google reviewTerri T — Google review
1879 Hooper Strait Lighthouse, CBMM
4.7
(155)
4.6
(165)
Historical landmark
Museums
Historical place museum
History museum
The 1879 Hooper Strait Lighthouse, located at the Chesapeake Bay Maritime Museum in Maryland, offers a glimpse into the spartan life of its keepers. This well-preserved 19th-century lighthouse served as a guide for boats passing through Hooper Straight. Visitors can explore the interior and climb to the top for stunning waterfront views. The museum provides insights into Maryland's maritime history, including shipbuilding and oystering.
The lighthouse and immediate area surrounding it are clean, safe and well-maintained. The grounds are fun to explore and easy to navigate. This is an amazing photo spot during the sunset magic hour. I look forward to my next visit as this was a worthy stop of the road trips..
Tom B — Google review
A neat piece of Bay nautical history, plus a great view of the bay.
It was very pretty view and the lighthouse was educational and cute
This lighthouse has quite an unique history which our museum guide shared with us. It was moved here years ago and inside furnitures and rooms have been preserved as best as possible. View of the bay was really nice, nice and windy.
What a treat it was to visit the inside of the lighthouse! It was a self-guided tour with lots of history. I've always admired it from the outside, and it was great seeing it and imagining living in it as a lighthouse keeper on the inside.
Incredibly well kept and restored. Make sure to take the day to tour all of the buildings and attractions. A plethora of information and history. Highly recommend
I have always loved lighthouses!This one was educational.I like the Thomas Point Lighthouse ,a lot!I believe it's a" screwpile" & flat & round in appearance!
Very cool lighthouse at the museum. You can go in and see what it might have been like to live in one.
213 N Talbot St, St Michaels, MD 21663, USA•
14 min · 0.72 mi
4•Elizabeth R — Google reviewKandis A — Google reviewAlice G — Google reviewRyan B — Google reviewLuxe D — Google reviewMegan P — Google reviewJoe Q — Google review
LYON RUM // Windon Distilling Company
4.8
(95)
4.8
(208)
Distillery
Food & Drink
LYON RUM, the flagship spirit of Windon Distilling Company, is located in Saint Michaels, Maryland at The Old Mill. Alongside Eastern Shore Brewing Company and St. Michaels Winery, Lyon Distillery crafts splendid rum and rye whiskey in small batches. Visitors can enjoy premium boutique wines at the winery's tasting room and savor seasonal specialties at the brewery while experiencing libation magic in the heart of St. Michaels.
After visiting St. Michael's winery (7/11), I was told to walk next door to LYON Rum distillery-woman owned! I did just that! The atmosphere was very inviting and fun. I can't remember the name of the person at the counter, but she was very friendly and knowledgeable about the distillery and products. The owner walked in, introduced herself, and provided additional information. I sampled some of the rums and purchased the Coconut rum and Blackberry (I think)...either way they were both amazing. I really enjoyed my time at LYON...and look forward to staying in touch through their email newsletter.
Carline P — Google review
We did a private tasting in the Golden Hour rum room which was fantastic. The space had a sleek, relaxed, speakeasy vibe that made the whole experience feel special. The owner herself led the tasting, and she was both knowledgeable and super entertaining. We got to try nearly a dozen rum samples, each with its own unique flavor, and learned a lot along the way. If you’re a rum lover—or just looking for a fun and laid-back tasting experience—this is definitely worth it. Highly recommend!
We visited after the St Michael’s running festival with our running club. We started in the tasting room/shop. The server was very knowledgeable as she was letting us sample the different flavors of rum. We then went into the speakeasy like space to have cocktails. The drinks were amazing. The service was exceptional. The owner interacted with all of the customers and even made us a delicious espresso martini that wasn’t on the menu. Definitely go! You will have a hard time deciding which bottles to bring home with you. We left with three.
Went for a tasting and thoroughly enjoyed both the rums and the hostess. She fully understood everything about the process and was able to answer all questions. I loved every single rum, except for the white, but that's because I'm not a fan of white rum to begin with. It was definitely palatable, however. I really wanted to buy more than one bottle (dark rum), but I am the only drinker in my house and didn't want something so tasty go to waste. I will definitely go back to visit and purchase again!
Lyon’s Rum Distillery has evolved with its newly created cocktails bar called, Golden Hour. Aptly named the sunny, speakeasy is a gem of hand crafted, Lyon’s rum centric cocktails. You will not only enjoy the well crafted and full bodied rum flavors but appreciate the care and passion of the craft put into the cocktails. For anyone who loves rum or just appreciates well crafted cocktails will bask in the sunset that Golden Hour presents.
Great place to visit with excellent customer service and a rum for everyone. Visited the shop after seeing their sampler package at a hotel. Very fun experience, the shop smells amazing, very good mix of branded goods and spirits. Sara, was very personable and knowledgeable. She provided several recommendations and recipes based on my palette. This business is definitely worth a visit.
The shop was on the small side but the service was outstanding! The employees were very friendly and knowledgeable about their products and not too pushy when it came to making sales. They gave great recommendations for using their rums in cocktail recipes. The token for the golden hour room was a fun surprise at the checkout station. Would definitely come back!
Super cute place. Nice service too. Drinks are delicious
605 S Talbot St UNIT 6, St Michaels, MD 21663, USA•
1 min · 200 ft
5•Kaycee F — Google reviewGlen M — Google reviewDebohra D — Google reviewEL — Google reviewA A — Google reviewJ M — Google reviewRedWhiteAndBrian — Google review
Classic Motor Museum of St. Michaels
4.8
(99)
4.5
(6)
Museum
The Classic Motor Museum of St. Michaels is an essential stop for anyone with a passion for automobiles while exploring the Eastern Shore. Nestled in a charming historic building, this museum showcases an impressive array of classic and antique cars spanning from the early 1900s to the vibrant 1960s. Visitors can marvel at everything from pre- and post-WWII classics to iconic muscle cars and sleek European sports models, alongside vintage trucks and motorcycles.
What a great museum! The staff were quite knowledgable and great to talk to. Not to mention how beautiful these cars are! I have added a picture of my favorite. It is $5 for children 5 and above, $15 for couples, and $10 for a single adult. I would say a great price for such a well kept museum. If you are into cars, this is a great place to go wether you are by yourself or with your family.
Clifton N — Google review
We really liked our visit to the Classic Motor Museum. The curator (owner?) was very eager to share his knowledge of the classic cars in the museum and the hostess was very friendly and helpful. There was a great selection of cars that helped us appreciate coach building from 100 years ago. It is evident how much care has gone into the collection and we highly recommend stopping in if you are a classic car enthusiast.
First time here. Small.place, but packed with great exhibits! Cars, motors, motorcycles, toys. Very nice, totally worth stopping in.
Went here a few weeks ago with my family and it was an absolutely WONDERFUL experience. The gentleman in the red shirt is a passionate fan of history and gave us such a fabulous and indepth tour of all the vehicles & the history of the automotive industry in America. If you dont get the chance to get a tour, the plaques and booklets in front of each car are still very interesting to read. I’m not a car person in the slightest but I will absolutely be returning next time I go to St.Michaels. Absolute gem of a museum and my favorite part of my trip here.
I heard that theyre likely expaning the museum to store more vehicles in the near future, which is very exciting.
However, I wouldn’t recommend bringing young children with no restraint as there is only rope in place to separate the vehicles from the patrons of the museum.
Cozy small museum.
But very interesting cladic cars on display. Good for the whole family.
Great museum. It's expanding to several buildings. Always interesting cars on display. The guide, Bill, is an encyclopedia of information about cars and industry.
This is a cool place to kill 30-60 minutes depending on your level of old car giveashitness. There are 3 antique MG's here and some old motorcyles and a bunch of other old things including the two guys that sit in the chairs as you walk in! Super nice folks, really nice original and restored vehicles. The red convertible was one of the very 1st vehicles to have headlights that turned as the vehicle turned. Stop in and say hi to the pretty lady at the "checkin"!
Small but very cool collection of vehicles. Would've like to see more domestic built vehicles but understandable that they cycle the collection.
102 E Marengo St, St Michaels, MD 21663, USA•
Create your ultimate travel itinerary
Plan your itinerary, find lodging, and import reservations — all in one app.
Where to eat
Under a 7-minute walk from Foxy's Harbor Grille, here are a few close by recommendations for when you get hungry exploring around.
Blu Miles
4.0
(137)
3.5
(19)
Restaurant
Bar & grill
Blue Miles, a seafood eatery situated in St. Michaels Harbor, offers a delightful spot for an informal lunch or dinner. Its prime location boasts a scenic patio and outdoor seating areas that provide breathtaking views of the sea. Additionally, the establishment prides itself on utilizing fresh ingredients sourced and crafted by local farmers and fishermen. This waterfront restaurant in St. Michael is renowned for its amiable staff and delectable cuisine, including their immense and flavorful soft shell crab and appetizing mussels.
A lovely evening with great friends sitting out on the patio watching the sun go down, ships cruising by, and having a great meal.
For dinner, we started with the oysters on the half shell and the coconut shrimp. Entrées included the broiled, seafood platter, pork chop, crabcake sandwich, and steak fajitas. All very good.
Our server (J) was attentive and quick to meet our needs.
We had made a reservation, but tonight it was really not necessary.
Great location, great food and great friends. What more could you ask for?
Ed V — Google review
This restaurant is located right on the water, near the water shuttle boat. We chose this location over the restaurant next door due to more menu options. It was not crowded and our party of 6 was seated right away. We were located inside with a water view of he marina. The food was pretty good. Lump crab in the dip and crab cake. The shrimp salad was thin with a lot of dill, but I enjoyed it. Overall, would come back here again! Support Local!
I arrived just after the kitchen closed. I had not had dinner yet so I asked if I could get something easy like a bowl of soup. The chef, Junior, came out and said he could make me anything I wanted. As much as I asked for something easy, he insisted he would cook anything. He offered a seafood special, so I agreed. Scallops, shrimp, a crab cake, mashed potatoes and broccoli. The scallops and shrimp were cooked and seasoned to perfection. The crab cake was one of the top rated crab cakes I have ever had. Overall it was a perfect meal for me. The bartender, Lessie?, was awesome too.
I went back the next day to get the crab cake sandwich with a couple of friends and we all loved it.
It’s a nice waterfront restaurant and friendly staff in St. Michael. Everything we had was really good. The soft shell crab is huge and delicious. The mussels were really good. My son had a grilled fish taco. He said it was really good, I could tell, he cleaned up his plate 😁 The price is very reasonable especially for a waterfront restaurant. It’s nice to sit at the patio, unfortunately it was really hot that day so we preferred to sit inside.
Not sure what happened. We used to love this place when it was the St. Michaels Crab and Steak and then when Blu Miles started, it was pretty good. We went there yesterday and had to send the food back. I got vegetable crab soup that first came out cold and then we had them heated up. It tasted like there was cleaning solution in it so we sent it back. I never send anything back.
The weight staff was very helpful, however.
Odd spot amazing location. Wait staff smoking cigarettes at the bar as they serve you. That was interesting. Good was really good and location in the water was great. We were there at 530pm on a Friday and we were the only ones there. Odd for a great waterfront location. Locals must know something us tourists don’t.
We happened here by chance because there was parking spot but decided to stay and so glad we did. It was a wonderful evening to sit outside under the moonlight. The owner (I believe that's who it was) was very welcoming and checked on the guests seated outside multiple times. Our waitress was very friendly, attentive, and accommodating.
The food was wonderful. The hubs and I started with soups: Maryland vegetable crab and cream of crab. Both came out piping hot, very tasty, and with plenty of crab meat. The oysters were good, on the smaller side, but had a nice ocean flavor. Rounding out dinner - Grilled chicken sandwich with pickled onions and coconut shrimp with a raspberry sauce. Lemon raspberry cake for dessert.
Lovely place to grab a meal and enjoy the time outside on the deck. Menu was short but sweet. We took our 2 youngest children ages 6 and 8 and they were very happy with the food and the outdoor atmosphere. The marina provides excellent views! Soft shell crab sandy was very delicious.
305 Mulberry St, St Michaels, MD 21663, USA•
Harrison's Harbour Lights
4.1
(281)
4.0
(162)
Seafood restaurant
Harrison's Harbour Lights is a chic waterfront restaurant that offers an upscale dining experience with stunning views of the marina. Guests can indulge in a delightful array of seafood, steak, and chops while enjoying the picturesque scenery of sailboats gliding by. The highlight here is their all-you-can-eat oyster buffet, featuring eight delectable preparations including raw, fried, and even crab-stuffed options. Dining on the second floor provides panoramic harbor views that enhance your meal.
We had a great dinner, yes the chicken and crab cake were amazing despite the past review of the chicken. The chicken was cooked perfectly, crab cake delicious, and fresh zucchini. They serve warm cornbread muffins with dinner and they are amazing! The service was great for dinner and breakfast. The views are wonderful!
Christine D — Google review
Nice place, perhaps a little past its prime.
The bar and restaurant servers were very friendly and made good food suggestions.
It was a shame that our room overlooked the trash bins and parking lot when there were only a few guests. The rooms with a great view of the bay went empty.
We were really looking forward to our dinner here tonight, and while the staff was friendly, we left disappointed by how a serious issue was handled or rather, not handled at all. I ordered the crab cake and fried chicken dish, but the chicken was almost entirely raw on the inside (photo attached.) When we flagged it to our server, there was no apology or sense of urgency. They swapped it for an extra crab cake only because we asked and we received an 'okay,' but no one from management ever checked in, and we were never offered a re-cooked meal, a discount, or even a simple “we’re sorry.”
We had a full meal: appetizers, entrees, and dessert, so the complete lack of acknowledgment was frustrating. Mistakes can happen, but what’s disappointing is how little was done to take responsibility for it. A friendly attitude is appreciated, but it doesn’t make up for undercooked poultry and silence from the team.
8NOV.2024 First time eating here and the panoramic views are beautiful while enjoying a meal and drinks on the second floor. A nice drive from Western Maryland to have a day in St. Michael’s.
Angie was wonderful and attentive. My glasses of Prosecco were delicious and crisp. My oyster 🦪 Rockerfeller took a bit to get to my table and they were ok(lots of spinach, I like spinach). Very fresh and tasted local(local is good). I’ve eaten better. The fried green tomatoes 🍅 were fresh and the batter could’ve been better. Delicious bits of crab meat on top and the sauce was good and different. The bacon 🥓 wrapped scallops were filling and well cooked through and through.
Nice local spot to drop in for good food and drinks. Everyone is very nice and welcoming here. You’ll be glad you stopped in.
We had an incredible time in the commodore suite. The Restaurant was incredible and it had a great view of the Marina. Our Servers were friendly and knowledgeable and the Food was presented well and quite tasty.
Mussels and corn bread were good. About the rockfish tacos: really good rockfish, not so good taco. Scallops: Overcooked, had to return the dish, unfortunately (the server had the courtesy of removing them from the bill). Nice view but overall wasn’t the best experience. Went to a different place for dessert.
We had dinner at Harbour Lights and had a great meal. The dining room was quiet in early May, and we walked in without a reservation around 530 PM on a Friday. We had a great view of the Marina and the dining room itself has great views all around. The menu is huge and they have seafood and non seafood options.
We ordered the crab dip, crab cakes, and rockfish imperial style. My husband also enjoyed the orange crush. All of our food was delicious and cooked perfectly. They serve delicious cornbread while you wait, and we also loved the coleslaw.
Great spot for a romantic date and views are spectacular.
The atmosphere is very nice and it over looks the water. The half and half crab soup was more like glorified tomato soup. It was awful and not very warm/hot at all. Our seafood extravaganza dinner was very good. At the end of our meal, our server didn’t ask if we needed anything else like dessert, coffee or tea, nothing. She just handed us the bill. I don’t think I have ever dined out where this has happened. I don’t think we will be coming back here.
101 N Harbor Rd, St Michaels, MD 21663, USA•
Need a place to stay?
Where
When
Navigate forward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.
Navigate backward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.
When
Navigate forward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.
Navigate backward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.
When
Navigate forward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.
Navigate backward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.
Travelers
2
Travelers
2
Gina's Cafe
4.6
(328)
4.5
(363)
Restaurant
Ginas Cafe offers a distinctive and enjoyable dining experience by combining a diverse Tex-Mex menu with Maryland's seafood. Situated in downtown St. Michaels, this restaurant and bar serves pescatarian-friendly dishes infused with Tex-Mex flavors, influenced by its sister establishment, Ginas Cantina in Millersville.
We stopped by Gina’s by chance. There are many fancy looking restaurants in St Michael’s. And frankly from the outside this isn’t one of them. But WOW is the food and drink a 5 star experience! It’s super fresh, delicious and so tasty. The margarita was made to perfection, I’m not exaggerating. The service was fast and friendly. They are only open until 5 I believe do get there by 4. You won’t be sorry!
Colleen H — Google review
The service and the atmosphere are outstanding. The heated outdoor tent is really cute and fun. We really enjoyed our outing. The food was only ok though. We got a bunch of different things. I got the Miami tango tacos which were ok. The sprouts were a bit intense on the tacos.
The nachos are almost the same as the dips. So it was a bit redundant that we got both of them. I would pick one. Maybe the dips because the chips were really fresh and delicious and crispy but you kind of lose that with the cheese. We got the chili melts which were pretty much like the two appetizers. So I’d recommend selecting one of these items.
The grilled cheese and tomato soup were not traditional. It was a quesadilla but the goat cheese and balsamic wasn’t a good addition to the flavors in my opinion. The tomato soup wasn’t creamy at all and was a bit too much of the overpowering fresh tomato flavors.
Overall amazing experience but not the best food. I’d come back for the fun experience and the chill vibe :)
Perfect way to end the day on our visit to St Michaels. A tad inconspicuous, but a real treat! Laid back casual vibe inside, outside seating available. Excellent Margaritas compliment a menu with a Mexican vibe but offering healthy options (no beef, pork or chicken). Service is perfectly on point.
Maybe I'm not a fan of Mexican food but I have had better elsewhere. We got the Shore Nachos, which had crab and homemade nachos. The crab was soggy and made the nachos wet and floppy. The cheese made up for some of it but I just was not impressed. The service and location are outstanding. I should have gotten another dish.
We must have got them on a bad day. Been coming here for years by boat and a normal go to and usually great food and great service. Not today. Drinks were way off service was OK and food seemed like it came out of a can. Taco salad was so soggy nobody could finish. Sorry but this just was not a good day
Nachos were big as your head. Excellent. Xango toriolla wrapped cheesecake. Spectacular. Talking with the staff the whole time. Like a family dinner. The best.
We just had the most fun at Gina's! The food was amazing! (thank you Angie!) and the margarita's!!!! the best!!! Our bartender was perfection! Thank you for delicious tacos, nachos, margaritas and the most attentive and kindest service!
Incredible, creative tacos and quesadillas. Fun cocktail menu. Friendly staff and loved the atmosphere. Would definitely recommend if you’re looking for a quick, delicious bite with a casual vibe!
601 S Talbot St, St Michaels, MD 21663, USA•
Theo's Steaks, Sides & Spirits - St. Michaels
4.5
(259)
4.5
(372)
expensive
Steak house
Nestled in the charming town of St. Michaels, Theo's Steaks, Sides & Spirits is a delightful blend of modern elegance and traditional steakhouse vibes. This inviting eatery boasts a menu that highlights expertly hand-carved steaks alongside an array of upscale appetizers and classic American dishes. The ambiance strikes a perfect balance between casual comfort and sophisticated dining, making it an ideal spot for both locals and visitors alike.
I almost cancelled my reservation because I figured I could get good steak in Washington DC where I live!! But I'm glad I didn't! The Steak Diane tenderloin medallions were incredibly tender, flavorful, perfectly seasoned - just like your website says. The Caesar Salad dressing was so delicious, green beans were buttery and perfectly cooked, and the cheesecake brulee was creamy yet light.
Perfectly crafted martinis and excellent, attentive service by Alissa Q. So so good, thank you!
Joe M — Google review
Very nice, charming and intimate place. Lots of nooks and crannies. Our room was intimate with only 4 tables
Our waiter, Chance, was very attentive without being intrusive. He was a delight! The food was amazing! We are not big eaters, but the portions look large. Special occasion, so we had champagne and dessert. Very understated curb appeal. Highly recommend, especially for a romantic dinner.
Pretty disappointed. Not a kid-friendly spot at all. It might work for most people, but we spend our weekends boating up and down the Chesapeake Bay and eating out with our 9-year-old daughter, who’s really well-behaved and likes food.
We stopped at Theo’s in St. Michaels, got seated, and asked the waitress if they had any kids’ options. She said they got rid of the kids’ menu completely and didn’t have any alternatives. The only thing they could offer her was a hamburger. We got up and left. Other upscale restaurants we've been to usually offer options or at least ask what our daughter likes.
Wow. Hands down some of the best steaks I’ve ever had.
We came here for a proper steak dinner, and it delivered big time. Kept it simple with mains and a few sides—onion rings, mushrooms, and fries. The onion rings were spot on, but the real star? The meat. I know my steaks, and these were cooked to perfection.
We ordered both medium, and as you can see in the photos, they came out exactly right. Went with the ribeye on the bone ($87) and the New York strip ($67). Pro tip: we asked for thick cuts, and the super friendly waitress made sure the kitchen nailed it just how we wanted. Couldn’t have asked for a better steak night.
Total cost with one glass of wine 262 including 20% tip
Had an excellent birthday meal served by Mr.Chance Miller. Service was outstanding!!! The waygu steak was chef kiss! The best key lime pie ever. Everything was delicious even the espresso. I can’t wait to return again. Thanks for the great hospitality on the eastern shore!!!!!!
Thoroughly enjoyed our dinner at Theo’s!
Food is top quality, prepared and presented beautifully. Service was friendly and on point.
Our reservation overlapped happy our so the noise generated by two women who no doubt had one too many was loud and annoying…fortunately when the hour ended and proceed returned to standard they left.
This can be resolved by simply reserving after 6:15PM.
We will return!
Very nice, high end restaurant! Recognized our anniversary with a complimentary glass of champagne to celebrate the occasion. Staff were friendly, food was fantastic, atmosphere was high end!
Chance was fabulous and welcoming. The food was delicious 😋 thank you for a lovely evening.
407 S Talbot St, St Michaels, MD 21663, USA•
Create your ultimate travel itinerary
Plan your itinerary, find lodging, and import reservations — all in one app.
Best-of categories in St. Michaels
Restaurants
Attractions
Cheap eats
Romantic places
Family restaurants
Museums
Shopping
Bars
Kid-friendly attractionsPopular road trips from St. Michaels
What's the weather like in St. Michaels?
It depends on when you visit! We've compiled data from NASA on what the weather is like in St. Michaels for each month of the year: see the links below for more information.
- Weather in St. Michaels in January
- Weather in St. Michaels in February
- Weather in St. Michaels in March
- Weather in St. Michaels in April
- Weather in St. Michaels in May
- Weather in St. Michaels in June
- Weather in St. Michaels in July
- Weather in St. Michaels in August
- Weather in St. Michaels in September
- Weather in St. Michaels in October
- Weather in St. Michaels in November
- Weather in St. Michaels in December
All road trips from St. Michaels
Explore nearby places
All related maps of St. Michaels
- Map of St. Michaels
- Map of Cambridge
- Map of Annapolis
- Map of Bowie
- Map of Solomons
- Map of Hanover
- Map of Baltimore
- Map of Oxon Hill
- Map of National Harbor
- Map of Washington DC
- Map of Alexandria
- Map of Salisbury
- Map of Ellicott City
- Map of Dover
- Map of Silver Spring
- Map of Mount Vernon
- Map of Arlington
- Map of Bethesda
- Map of Milton
- Map of Sandy Spring
- Map of McLean
- Map of Havre de Grace
- Map of Rockville
- Map of Potomac
- Map of Woodbridge
- Map of Vienna
- Map of Marion Station
- Map of Fairfax
- Map of Lewes
- Map of Rehoboth Beach
- Map of Reston
St. Michaels throughout the year
Looking for other day-by-day itineraries in St. Michaels?
Check out our other curated itineraries that are also filled with jam-packed days:
Day itineraries for nearby cities
- 2-Day Washington DC Itinerary
- 2-Day Baltimore Itinerary
- 2-Day Annapolis Itinerary
- 2-Day Alexandria Itinerary
- 2-Day Arlington Itinerary
- 2-Day Rehoboth Beach Itinerary
- 2-Day Lewes Itinerary
- 2-Day Fairfax Itinerary
- 2-Day Rockville Itinerary
- 2-Day Dover Itinerary
- 2-Day Silver Spring Itinerary
- 2-Day Bethesda Itinerary
- 2-Day Cambridge Itinerary
- 2-Day Havre de Grace Itinerary
- 2-Day Salisbury Itinerary
- 2-Day Woodbridge Itinerary
- 2-Day Ellicott City Itinerary
- 2-Day McLean Itinerary
- 2-Day Vienna Itinerary
- 2-Day National Harbor Itinerary
- 2-Day Reston Itinerary
- 2-Day Solomons Itinerary
- 2-Day Milton Itinerary
- 2-Day Potomac Itinerary
- 2-Day Bowie Itinerary
- 2-Day Hanover Itinerary
- 2-Day Oxon Hill Itinerary
- 2-Day Sandy Spring Itinerary
- 2-Day Mount Vernon Itinerary
Planning a trip to St. Michaels?
Save all the best places to visit with WanderlogDownload the travel planning app everyone's been raving about
- Itinerary + map in one view
- Live collaboration
- Auto-import hotels and reservations
- Optimize your route
- Offline access on mobile
- Optimize your route
- See time and distance between all your places
