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2-Day Winchelsea Itinerary

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Wanderlog staff
Updated
• updatedAug 21, 2025

Winchelsea in 2 days

If you only have 2 days to spend in Winchelsea, we’ve narrowed down the top places you should check out to get the best experience of your time here.
With favorites like William the Conqueror, Church of Saint Mary, Rye, and Winchelsea Town Well, 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 Simon The Pieman and The Ypres Castle Inn so you can get the best taste of Winchelsea 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 Winchelsea?
  • 1-Day Winchelsea Itinerary
  • 3-Day Winchelsea Itinerary
Visiting Winchelsea? See our Winchelsea Trip Planner.
Feel free to follow our itinerary exactly or tailor it to your own needs — happy wandering!
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Table of contents
  • Winchelsea in 2 days
  • Most popular attractions
  • Northeast side of town

Day 1

Most popular attractions
For day 1, we strategically grouped the most popular attraction, Rye, 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 7 hours of your day.
1

William the Conqueror

4.4
(1478)
•
4.1
(748)
$$$$affordable
Pub
Restaurant
Nestled near Rye Harbour, the William the Conqueror pub is a delightful spot that perfectly blends traditional British fare with Mediterranean flair. After a day at Camber Sands, this dog-friendly establishment welcomes you and your furry companions with open arms. The menu features classic pub dishes like burgers and fish and chips alongside enticing Greek options such as homemade moussaka and chicken souvlaki.
A business friend of mine ate here last night. He has a Greek wife and told me it was the best Greek food he'd had outside Greece. So I gave it a go!! indeed, the food is delicious. The location on Rye harbour is beautiful an atmospheric I ate outside and had the feta cheese saganaki and the moussaka. The cheese that starter was exquisite. The moussaka is not enormous but probably the freshest and tastiest I have had in the UK too, it tasted genuinely homemade and came with a lovely fresh Greek salad. The prices are probably slightly higher than some pubs nearby but you pay for the quality and it's certainly worth it, I am very happy to endorse my friend's statement about some of the best Greek/Cypriot food I've had in the UK.
Neil — Google review
William the Conqueror in Rye offers a pleasant atmosphere and is a good option in the area. However, the food prices are comparable to London, but the dishes lack the depth of flavor and appeal one would expect at that price point, despite being filling. Additionally, there was no check-back on the food.
Farhoud S — Google review
Lovely range of yummy Greek and Cypriot food, we enjoyed the Halloumi pitta and Cyprus mix. Prices were reasonable, portions were generous and staff were all friendly and attentive.
Steph G — Google review
We are on holiday staying at Camber, we always visit this lovely pub for food. My husband had the Tiger Prawns and I had the grilled halloumi salad with fries and pitta bread delicious 😋
Susan B — Google review
We decided to eat here because it wasn't busy, we had parking outside and they offered Greek food which we really enjoyed. Good service and great pub, nice decoration.
Marta F — Google review
What a lovely public house, situated right by the Harbour. The staff were extremely friendly & the service was super quick. We had the chicken souvlaki & Cyprus mix. The portions were generous & both very tasty. They also cater for GLUTEN FREE & take extra care when informed of the allergen. Would highly recommend.
Jodee H — Google review
I recently had a fantastic meal at William the Conqueror, a charming pub near Rye Harbour. My partner and I spent £33 for two incredibly filling dishes: I thoroughly enjoyed my delicious vegan Halloumi Burger, and my partner raved about their baked Risotto. The pub itself is a friendly, no-frills local spot, reportedly dating back to the 1890s. It's known for its good quality food, including traditional pub fare and Greek specialties (the landlord has Greek Cypriot heritage!). You can even eat outside near Rye Harbour when the weather's good. It tends to be popular with tourists during the summer and weekends, and they sometimes have live music. It's a great spot to relax over a meal and a pint, close to the picturesque Rye Harbour.
Shreyans M — Google review
Nice pub with a good menu, but not too fancy. Food was good, as was the Guinness and friendly service. Too full for a desert, but they also looked good. Smallish but free car park belonging to the pub, and a much larger one within a couple of minutes walk. Recommended, and we'll be back.
Mark L — Google review
Rye Harbour, Rye, TN31 7TU, United Kingdom•https://www.williamtheconqueror.co.uk/•+44 1797 223315•Tips and more reviews for William the Conqueror
6 min · 2.7 mi
2

Church of Saint Mary, Rye

4.7
(400)
•
4.5
(829)
Anglican church
Sights & Landmarks
Historic Sites
Churches & Cathedrals
The Church of Saint Mary in Rye, a historic Episcopal church dating back to the 12th century, offers visitors a rich experience. The church features a visitor center providing ample information and the opportunity to climb its bell tower for stunning views of Rye's rooftops, harbor, and sea. This classic English village church boasts over 900 years of history and showcases various architectural styles.
This is a lovely church to visit. We came here twice during our short visit to Rye. They have a series of short leaflets explaining the various aspects of the church, such as the Tower, the Windows and the Clock, each costing only £0.25. Entrance is free, but there is a small charge to climb up to the tower, which is well worth it if you can manage the 84 steps up very narrow stairs and corridors. You are rewarded with great panoramic views over the lovely Rye Town and the surrounding landscape and River Rother.
T H — Google review
A big church for a small town indicating the cinque port status and importance of Rye in medieval times. An interesting interior with plenty of information panels. The only church I've seen where the clock pendulum extends into the nave. For £5 you can climb the tower and view the clock mechanism and the bells up close. From the tower roof there are fantastic views.
Herm D — Google review
If you visit Rye, you simply cannot mis this Church. It's right in the center of the town. If you managed to climb up to the top of the church, you can get a clear and unobstructed view of the entire town of Rye. And there are a lot of old bells stored on the clock tower.
Michael P — Google review
Beautiful and historic church in the old village of Rye. This historic church has been a dominant feature of the town for over 900 years. However it was extensively damaged in 1377 during a raid by French invaders but was later restored. It has one of the oldest working church turret clocks, installed in 1561-2 and the clock's pendulum swings in the body of the church. An additional feature is the Victorian stained glass windows, Plus for a real treat you can also climb the church tower for a panoramic view of Rye.
Ross D — Google review
Great architecture, ancient church with access to the bell tower and roof. Just a shame they decide to be political.and fly a Palestinian flag instead of the union flag or st George flag
Tony J — Google review
Lovely church. I would recommend taking a trip up the tower. Whilst you do need to pay, this gets you a year pass. The views from the top are well worth it. It's also very interesting passing through the bell chamber and past the bell frame. The passage way is a little narrow, and obviously there are steep steps.
Richard G — Google review
Well worth a visit. The stories and myth that surround this place add a magical element. While lighting a candle, you get the sense that you are listened too. I cannot recommend this church enough.
Hollie S — Google review
Such a peaceful vibe - lovely church - welcoming volunteers and soulful surrounds. Worth a visit and a prayer 🙏🏽
Jane J — Google review
Church Square, Rye, TN31 7HF, United Kingdom•http://www.ryeparishchurch.org.uk/•+44 1797 222318•Tips and more reviews for Church of Saint Mary, Rye
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Where
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Travelers
2
Rooms and guests
Rooms
1
Adults
2
Children
0
Travelers
2
4 min · 0.22 mi
3

Rye

5.0
(68)
Outdoor Activities
Hiking Trails
Rye is a charming English town located near the coast in East Sussex. Its center features picturesque cobbled lanes lined with medieval, half-timbered houses and the historic redbrick Lamb House, once owned by writer Henry James. The Norman St. Mary’s Church overlooks the town from its tower, while the 14th-century Ypres Tower now houses the Rye Castle Museum, showcasing local history through paintings and displays.
UK•http://www.ryetowncouncil.gov.uk/•Tips and more reviews for Rye
6 min · 2.7 mi
4

The Strand Gate

4.7
(10)
Historical landmark
The Strand Gate, a well-preserved medieval structure in Winchelsea, East Sussex, is a testament to the area's rich history. Dating back to the 14th century, this single-lane gate was originally even taller and featured two portcullises. Today, it offers excellent views of Rye Harbour Nature Reserve and Camber Castle. As visitors pass through the gate or explore its interior, they can appreciate its enduring construction and learn about its significance through informative blue plaques.
Well preserved medieval gate at the southeast corner of Winchelsea, from which there are excellent views over Rye Harbour Nature Reserve and Camber Castle. The road still heads through the gate, but it's possible to walk inside the gate to get a closer look at the construction. The gate is now only two thirds of its original height. Like many historic buildings in Winchelsea, there's a blue plaque on the gate outlining its history.
Andrew T — Google review
Winchelsea is a beautiful location. By walking the quiet streets a lot of interesting history becomes evident. The Strand Gate, built in the early 14th century.
Clara F — Google review
Winchelsea is a beautiful location to visit when in East Sussex, just by walking the quiet streets a lot of interesting history becomes evident. The Strand Gate, built in the early 14th century, would have overlooked the old port of Winchelsea when built and would have been a clearly visible impressive structure when first seen by visiting ships. Take time to look around and enjoy the views as well as the history, if you look hard enough you can see the remains of Camber Castle from here.
Ian M — Google review
Historic gate acting as an entrance to Winchelsea. Access via a steep incline from the main A259. Two way traffic passes through this gate but is only wide enough for one car at a time and so there is a mirror to allow you to see if there is oncoming traffic.
Ian F — Google review
Interesting historical site.
Julie K — Google review
A beautiful place with outstanding views.
Lynn C — Google review
Cool historic feature
Robert W — Google review
Really nice village, be careful when driving around area.
Steve S — Google review
1 Strand Hill, Winchelsea, TN36, United Kingdom•Tips and more reviews for The Strand Gate
4 min · 1.4 mi
5

Winchelsea Beach

4.3
(331)
Outdoor Activities
Beaches
Winchelsea Beach is a charming seaside village situated in the parish of Icklesham in East Sussex, England. It's positioned around 10 miles east of Hastings and about 1.5 miles southeast of Winchelsea. The beach overlooks Rye Bay and the River Rother estuary, offering a gently sloping shingle beach that stretches for miles during low tide.
Winchelsea, TN36 4NA, UK•Tips and more reviews for Winchelsea Beach
8 min · 1.4 mi
6

Mary Stanford Lifeboat House

4.3
(147)
•
3.4
(29)
Historical landmark
Association / Organization
Nestled in the serene landscape of Rye Harbour, East Sussex, the Mary Stanford Lifeboat House stands as a solemn tribute to the courageous lifeboat crew who perished during a harrowing rescue mission in 1928. This historic structure not only commemorates their bravery but also serves as a poignant reminder of sacrifice amidst nature's beauty.
Lonely former lifeboat house standing as a reminder of the tragic 1928 disaster, which resulted in the loss of the Mary Stanford lifeboat and all crew members in a terrible storm. On a sunny day it's hard to imagine the terror the crew must have experienced, as the surrounding nature reserve and coastline seems so peaceful. There's an information board covering the story of the Mary Stanford in more detail. The walk from Rye Harbour Discovery Centre is easy, on level paths with good views over the nature reserve known for its bird life. There's a tremendous sense of space here thanks to the large area of open land.
Andrew T — Google review
The Mary Stanford Lifeboat House represents an interesting piece of history but is it worth visiting for itself? Not really as it's basically a shed, that you can't enter, and an information sign. It does make for a good photo opportunity though. This is because it is in a striking setting next to the beach and the walk through the nature reserve is very picturesque. So if you're in the area and strolling along the path then there's no reason not to stop by. Just don't expect a tearoom!
Damian C — Google review
A nice walk round the reserve to discover this building. Was rather quiet which gave an atmospheric feeling after reading what happened there.
Alan T — Google review
Along with Dungerness and the isolated, desolate west coast of the Romney Marsh, this is one of the most enigmatic and solitary places on the South Coast. However, the poignancy of the tragic story which unfolded here a century ago makes it a monument to bravery and self sacrifice. I slept 200 meters away, bivvy style over night, as was walking the coast and wanted to get some good light photos. It's truly a stunningly beautiful place that leaves a great impression on your imagination afterwards.
David C — Google review
True but very sad piece of history at this hut in memory of the life boat men who lost their lives from here. Can visit from the cycle/ walking path from winchelsea to rye harbour about the half way point. Lovely walk or cycle on flat ground. Can park near the toilets. Cafe near by too next to the caravan park.
Jo — Google review
Here the story is told of how a lifeboat crew tragically lost their lives whilst trying to rescue a ship caught in a storm. The lifeboat house is in a wonderfully remote and peaceful area of outstanding natural beauty. A lovely place for dog walking and, or bird watching.
Chris H — Google review
Such a sad story about the life’s lost of all the crew. This beautiful building should be restored to its original glory in memory of all those who died. Worth every step to find this place
A B — Google review
Very nice quiet place - lots of local info signs placed to see old and new photos inc the tragic story of the loss of life at sea
Ash P — Google review
Harbour, Rye, TN36 4LU, United Kingdom•http://www.marystanford.org.uk/•Tips and more reviews for Mary Stanford Lifeboat House
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Where to eat

Even the most seasoned adventurers need a break to chow down some food. Close to Church of Saint Mary, Rye, these restaurants are about a 1-minute walk away.

Simon The Pieman

4.1
(266)
•
3.0
(458)
$$$$affordable
Tea house
Cake shop
Nestled in the heart of Lion Street, Simon The Pieman proudly claims its title as the oldest tearoom in the area, making it a charming spot for a light lunch. This delightful establishment not only serves an impressive selection of savory pies but also boasts a tempting cake shop that draws visitors in with its mouthwatering displays.
Wow the scones are awesome. We had cream tea and got to experience the best scones, jam and cream I’ve ever had. The scones are light, fluffy and delicious. The service was great, with the staff being friendly and attentive. Very happy we chose Simon the Pieman for our tea break, it was well worth it.
Laurie M — Google review
We ate here as it was dog friendly but the food was mediocre at best. The offer of a warm sausage roll ended up being one that had been microwaved and of course the pastry was soggy. We also had a baked potato which was barely warm. The cakes looked good but we didn't sample them.
Andy K — Google review
A very nice place to hang out and chill 😀 I tried their Cheese and Onion pastry and Carrot cake! Both were so delicious 🤤 and I would definitely recommend this place to everyone! One of the best places to eat in Rye. Amazing experience it was!! 😍
VIDHI M — Google review
Came in for some lunch today whilst visiting Rye and it was wonderful. Panini's were nice and fresh, tasted delicious and the staff were lovely and accommodating, especially the lovely waitress in the pink jumper :) thank you! My only regret was not trying any of the cakes or pastries, they looked delicious. We will definitely be back if we’re ever visiting again :)
Holscal 9 — Google review
Very basic food served by friendly staff in what is the oldest tea room in Rye. Had better sandwiches from a supermarket, over priced for what you get, to be expected as it’s a tourist destination. Not unpleasant, just not good value for money.
Scott B — Google review
Lovely to visit Simon The Pieman Tearooms in Rye. They not only do really tasty cakes and pastries to take away. The scones were only £1. They also do meals inside, brilliant home cooked food and very reasonablely priced. I had cottage pie and then some mince pies with cream, both very very filling and tasty. The pot of tea, even came with another jug of hot water to top up the teapot. A very old traditional Tearooms, with an open fire, very welcoming in this cold wet weather. The staff are lovely friendly and helpful. Well worth a visit, right next to the church and cinema. #simonthepieman #simonthepiemanrye
Venetia C — Google review
To be avoided. The location is beautiful, the staff is friendly, and the cottage pie was nice, which prevents this from becoming a 1 star review. The quality of the rest of the food was below par. And charging 5 pounds for a tiny amount of lettuce as a side salad is daylight robbery.
Jorrit H — Google review
Lovely little restaurant with great food and service. The food is excellent and very tasty. The cakes are devine. Great place for tea and cake or a proper meal. The location is a nice historical building, great setting to enjoy from local food. I can highly recommend.
Michel L — Google review
3 Lion St, Rye, TN31 7LB, United Kingdom•+44 1797 222207•Tips and more reviews for Simon The Pieman

The Ypres Castle Inn

4.5
(977)
•
4.5
(746)
$$$$affordable
Pub
Nestled in a charming old-world pub, The Ypres Castle Inn offers a cozy atmosphere with plush velvet booths and a roaring fireplace. The inn features an ever-changing selection of guest beers, including Sussex-based ciders and locally produced vodka or gin from Kent. Guests can also enjoy delicious charcuterie boards and local cheeses while sipping on their favorite brews in the welcoming pub or spacious beer garden.
A near old-school pub with a lovely beer garden and a good selection available. I love the no fuss interior. It's in a great quiet, tucked away location.
Jennifer K — Google review
Great little place for people that like pubs the breweries haven't commercialised. Great beers and ciders that are different from the usual everywhere and a great stout (called Blacks) that's a lovely change from Guinness. They do good cheese plates and pork pies. Open log fire with very friendly staff. The owner is there in the bar most of the time chatting to everybody everywhere. He loves his 'work' and creates a very welcoming, open atmosphere. Nothing is fancy, but it's all very authentic and honest. If you're in Rye and looking for a pleasant distraction for a couple of hours, seek it out. You''ll probably be pleased you did.
David S — Google review
Came here about ten years ago and once again starting off the day here. Liza kicks off with a Langudoc rosé. I had a Kent brewery 4.1% Golding. Lovely pint. Two real ales and a cider on handpump. A beautiful pub in a great setting. Friendly staff. Large walled beer garden with views over the wetlands to the sea. Looks like decking also being built. Only bar snacks and pork pies: not a food destination.
MADDOGLEP — Google review
Chilled out pub with a great beer garden, dates back to the 17th Century. We visited on a Sunday evening so there was only one cask ales on (they shut Monday - Weds), but there is a good choice of other drinks. Dog friendly. They don't serve food and access is down some steep steps.
Diane R — Google review
We had a lovely visit to the Ypres Castle Inn – the perfect spot to enjoy a cool drink in their beautiful beer garden. We sampled some of the bar food and were not disappointed – the cheese and pickle roll was delicious, and the large pork pie was absolutely spot on. The service was warm and welcoming from the moment we arrived. We actually turned up a little early before opening, but they were incredibly accommodating and made us feel right at home. A hidden gem with great atmosphere and friendly staff – would definitely recommend!
Amy W — Google review
Great old vibey little inn serving local ales, ciders and more. Well worth checking out after a visit to the 'castle' Pop down the stairs afterwards and you can go grab some lunch at the fish market and seafood bar! Perfect!
Stripealipe — Google review
Smells like an old book. Love this pub. Will be back.
Bradleigh H — Google review
Stumbled into this lovely little country pub on a beautiful day in Rye. Fantastic selection of beers and ciders, many from Sussex but lots from around the world. Beautiful beer garden, cozy fire, what more could you ask for?
Seth K — Google review
Gungarden, Rye, TN31 7HH, United Kingdom•http://yprescastleinn.co.uk/•Tips and more reviews for The Ypres Castle Inn
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Travelers
2
Rooms and guests
Rooms
1
Adults
2
Children
0
Travelers
2

Simply Italian

4.5
(1177)
•
4.4
(1727)
$$$$affordable
Italian restaurant
Simply Italian is a family-run, relaxed restaurant that offers classic regional Italian dishes. With a few locations across the South East, this traditional eatery in East Sussex serves freshly made pizza topped with quality ingredients like mozzarella and spicy nduja. Other menu highlights include spinach and ricotta cannelloni, spaghetti carbonara, seafood risotto, and homemade tiramisu for dessert. The atmosphere is cheerful and bright, offering a no-frills dining experience with simple yet delicious food.
We stopped at Trattoria for lunch back in March 🍴. Lovely atmosphere ✨, staff very helpful 😊 and food was nice 😋. The butternut squash risotto had a bit too much butternut squash for our liking, but the rest of the food was delicious 🍝.
Rasa J — Google review
I love Italian food and I have found a gem in Rye. So so good, the mussels were so delicious. The calamari was soft and lovely. The lobster ravioli was so flavourful, loved it. The chicken risotto was light and tasted good. The wines were good and the homemade tiramisu was light, just the right sweet and so nice. Highly recommend.
Ananya M — Google review
We stayed in Camber Sands Rye for 3 days and we came back to this restaurant twice for the lovely food, great decor and atmosphere and amazingly friendly staff. But it was the tiramisu that made us comeback right the following day 😋 Good prices for the quality of the food. Everything was so delicious! Highly recommended and can’t wait ti comeback!
CecilleJennette A — Google review
I was there Saturday 12/07, food was nice service was bad. Our server refused to let us move inside despite having a child who was cold. There were plenty of tables inside. She refused to have a candle lit on the cheesecake to celebrate my wife's birthday claiming it was too windy. Not going there again. Notice the candle hole on the cheesecake. Reply to the comments from the manager: first of all the other comments are from my friend, second she suggested to light the candle at the table after we ate half of the cheesecake. I guess I'll eat Italian food in another that thinks the customer is right.
Atef Z — Google review
If you're looking for rustic and authentic Italian food, this is the ideal place! 10/10. Ordered marguerita and pepperoni pizzas for the teens, seafood spaghetti, garlic bread and tagliatelle con funghi! Absolute delight. Apologies we ate the food as soon as it came to the table. Bought extra portions of home made tiramisu as it was absolutely gorgeous!
SnapNSpill — Google review
Great restaurant with lovely service. But the stand out is the food. Absolutely delicious! I took the Seafood spaghetti and a chocolate Sundae ice cream. Will definitely recommend
Nicola D — Google review
Nice restaurant in Rye with friendly staff, lot of space and good options in the menu. A great option for Italian food lovers living or visiting Rye.
Ricardo A — Google review
This is our third time visiting Simply Italian. Food is good as always, however the service we received this time was not so professional. Particularly from the young female staff who was serving us today.
Chiho C — Google review
12 Strand, Rye, TN31 7DB, United Kingdom•https://www.simplyitalian.co.uk/•+44 1797 226024•Tips and more reviews for Simply Italian
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Day 2

Northeast side of town
For day 2, we recommend exploring the northeast side side of town. Start the day off with Spike Milligan's Gravestone, then wind down and take it easy by the time you get to The Pipewell Gate. All together, your day would be filled with about 7 hours of non-stop fun.
1

Spike Milligan's Gravestone

4.5
(188)
•
4.6
(21)
Historical landmark
Spike Milligan's gravestone is located at St Thomas's Church in Winchelsea, East Sussex. The comedian passed away in 2002 at the age of 83, and his famous epitaph "I told you I was ill" was added to his gravestone after a dispute among his family members. This witty inscription marks the end of a bitter feud and serves as a humorous tribute to the beloved ex-Goon.
The famous epitaph on Spike Milligan's gravestone, "I told you I was ill", has been added to , at the end of a bitter feud between the ex-Goon's family members. The comedian died in 2002, aged 83, and was buried at St Thomas's Church in Winchelsea, East Sussex
Beatrix B — Google review
Well worn path can’t miss it. In a spectacular little village.
Steve L — Google review
Well worth a visit to see the legends gravestone if you’re in the area. It’s a lovely church and surrounding village too. Nice pub on the corner, makes for a fun few hours.
Patrick C — Google review
I did not visit Spike's grave, but I am sure it is there somewhere. Winchelsea itself was like a ghost town when I visited with only a corner shop and pub open. A few sights scattered through the town and a museum that was closed. Although this was probably due to H.M. The Queen passing on the day before.
Ian D — Google review
A great place to visit, wonderful church, lots of people had left coins and small stones around his grave.the village is peaceful and beautiful houses with a small independent shop.a great afternoon spent there
Bertie P — Google review
This may sound obvious but it is just a grave stone, and incase you are wondering it does not say "I told you I was sick" actually it is very hard to read. On saying the above, he was a big part of British comedy history and if you are near by in a very attractive village then worth a look at.. There was a few visitors there when we went, and it is pretty easy to find, turn your back on the church and follow the grass path that is very warn by other visitors.
Adrian B — Google review
Have visited a few times, there is a well trodden route leading to the grave. Spike was a very popular character.
Mick P — Google review
A humble gravestone with pebbles and coins as momentoea
Claire T — Google review
German St, Winchelsea, TN36 4EN, United Kingdom•Tips and more reviews for Spike Milligan's Gravestone
1 min · 400 ft
2

New Inn

Transport hub
When exploring the charming town of Winchelsea, you'll discover a variety of delightful accommodations to suit your preferences. Among them is the inviting New Inn, which offers a warm and cozy atmosphere perfect for unwinding after a day of adventures. Whether you're looking for a peaceful retreat or simply want to enjoy the local hospitality, New Inn provides an ideal base for your stay in this picturesque area. Don't miss out on experiencing its unique charm during your visit!
Winchelsea, TN36 4EN, United Kingdom•Tips and more reviews for New Inn
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2
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Rooms
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Adults
2
Children
0
Travelers
2
2 min · 0.13 mi
3

Blackfriars Barn and Cellar

4.3
(3)
Historical landmark
Blackfriars Barn and Cellar, located in Winchelsea, is a 14th-century ruin managed by the National Trust. Believed to have belonged to the local Dominicans, the Black Friars, it offers a glimpse into history with images of 12 ships considered medieval graffiti. The site provides striking views of the surrounding countryside and while access to the barn may be restricted due to safety concerns, visitors can still appreciate its historical significance from outside.
Remnants of Blackfriars Barn and Cellar. The cellar of course being below ground, but you can see the cellar doors which are located near the roadside. The site is owned and managed by National Trust. Currently unable to go in the 'barn', as they are concerned about the cellar ceiling collapsing.
Ian F — Google review
Striking ruin in the care of the National Trust, situated by the roadside and overlooking good views of the surrounding countryside. Access to the barn was prohibited when I visited due to safety concerns, but it's still possible to get a good view in from outside.
Andrew T — Google review
Winchealsea is a lovely place to walk around, with places of interest like Blackfriars barn & cellar, the well, St Thomas church and beacon view point with gorgeous scenery and walks
Nicola D — Google review
Icklesham, Winchelsea, TN36 4HH, United Kingdom•https://www.winchelsea.com/the-town-story/town-trail/black-friar…•Tips and more reviews for Blackfriars Barn and Cellar
2 min · 0.1 mi
4

Winchelsea War Memorial

4.7
(3)
•
4.5
(4)
Park
(Translated by Google) I'm not a fan of the church garden, but I'm very impressed by this place 🥰 it's a wonderful place (Original) Nem rajongok a templomokert, de nagyon megfogott ez a hely 🥰 csodalatos hely
LUCK S — Google review
St Thomas Churchyard, High St, Winchelsea, United Kingdom•http://warmemorialsonline.org.uk/node/106822•Tips and more reviews for Winchelsea War Memorial
1 min · 200 ft
5

Church of St Thomas, Winchelsea

4.8
(97)
•
4.7
(238)
Episcopal church
Sights & Landmarks
Churches & Cathedrals
The Church of St Thomas in Winchelsea is a historic and peaceful place with a lot of local history. The ruins around the church create an atmospheric setting, and the beautiful architecture and interior make it a must-see for history enthusiasts. The churchyard features magnificent stained glass windows dating back to the early 20th century, designed by Scottish artist Douglas Strachan. Additionally, visitors can admire impressive stone tombs built into the walls and a large organ inside.
Outstanding church at the centre of the picturesque small town of Winchelsea, with atmospheric ruins in the churchyard and magnificent stained glass windows. The windows date from between 1929 and 1933, and were designed by Scottish artist Douglas Strachan and gifted by Scottish barrister Robert Younger. They are themed with biblical scenes, war memorials and local imagery. Other notable features inside include the impressive stone tombs built into the walls, and the large organ. Construction of the original gothic church building began in 1288. However, the building was extensively damaged in a French raid in 1380, and its condition deteriorated over the next five centuries. By the early 1800s, the building was at risk of collapse, but was extensively restored in 1850. Today, it is beautifully maintained, and a credit to the town. There's unrestricted parking available on nearby roads for visitors to the church, and information books inside the church detailing its history and significant features. The Easter flower arrangements inside were lovely to see.
Andrew T — Google review
St Thomas church is in Winchealsea which is lovely place to walk around. It has gorgeous stained glass windows, grave stone of Spike Milligan in its grounds, nice places to sit down outside and building open to go in.
Nicola D — Google review
Wonderful church to look around, the stained glass windows are very beautiful. The pillars with old sea farmers graffiti on are good to amuse children of all ages. Also the graves of what looks like medieval knights or noble men are very well displayed! To finish off out side is Spike Milligan's grave!
Andy F — Google review
This church has such immense history, this alone is impressive, but seeing the remnants of the church as you approach leaves one speechless when you enter the actual church. It is very large and most impressive. But for me, the fact that this is the final resting place of Spike Milligan, whose tombstone can be found just outside the church entrance, was simply a wonderful experience. Winchelsea is a beautiful place to visit, simply amazing.
Douglas G — Google review
Lovely peaceful church, full of history with amazing tombs. Also the grave of musician and comedian Spike Milligan.
Kenneth M — Google review
Positioned fittingly in the centre of Winchelsea is the church dedicated to ‘St Thomas the Martyr’ – Thomas Becket, Archbishop of Canterbury.  A really peaceful historic church. Well worth a look around. There is a lot of history within the area. The architecture and interior are beautiful and a must for local history enthusiasts. The grounds are so peaceful and absolutely wonderful with all the Graves and flowers everywhere. Took me a while to walk around and absorb the beauty of it all.
Beatrix B — Google review
Beautiful church definitely worth visiting!
Vendulka P — Google review
Lovely very old historical church with Spike Milligans grave in the graveyard Big stained glass windows in memory of those whose lost their lives in the First World War.
S F — Google review
Monks' Walk, Winchelsea, TN36 4EB, United Kingdom•https://winchelsea-icklesham-churches.org.uk/•Tips and more reviews for Church of St Thomas, Winchelsea
2 min · 400 ft
6

Winchelsea Town Well

4.3
(9)
Historical landmark
Located on Castle Street, the Winchelsea Town Well is a unique pyramidal building that houses a well gifted to the community by Thomas Dawes in 1851. The Victorian structure incorporates medieval arches and buttresses, with a shaft plunging 130 feet down lined with red brick. While access to the pump workings is restricted behind locked gates, visitors can still catch a glimpse inside.
BEAUTIFUL church, wonderful stain glass windows. Pretty well kept houses and a very good museum telling the history of the town.
Gillian Y — Google review
Attractive historic well building that still houses the pump workings. The gate was locked but it's still possible to see inside. Worth a passing look if you're visiting Winchelsea as it's only a short walk from the village centre.
Andrew T — Google review
The whole town of Winchelsea is steeped in history, the well is a landmark, but there is not much to see. I was told the actual well ,which is covered by boarding is 100 feet deep
Mick P — Google review
Winchealsea is a lovely place to walk around, with places of interest like the well, St Thomas church and beacon view point with gorgeous scenery and walks
Nicola D — Google review
Town well dating back to 1851. Surrounding building has been well maintained. Access to the pump itself is not permitted as behind locked gates but you can still see the mechanism quite clearly.
Ian F — Google review
Pretty little well house. Another historic site in this beautiful little town. Only take a couple of minutes to see.
Francesca P — Google review
It's a lovely town to have a brief look around.
William M — Google review
1 Castle St, Winchelsea, TN36 4HU, United Kingdom•Tips and more reviews for Winchelsea Town Well
4 min · 0.21 mi
7

The Pipewell Gate

5.0
(1)
Historical landmark
The Pipewell Gate, also known as the Strand Gate, is a remarkable 13th-century structure that still allows traffic to pass through its single lane. This enduring construction was originally even taller and featured two portcullises. It stands as a testament to the lasting architectural prowess of its time.
1 North St, Winchelsea, TN36, United Kingdom•Tips and more reviews for The Pipewell Gate
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Where to eat

Under a 5-minute drive from The Pipewell Gate, here are a few close by recommendations for when you get hungry exploring around.

The Ship Inn

4.1
(1275)
•
4.1
(357)
Restaurant
Hotel
Pub
The Ship Inn is a charming 16th-century inn located in the medieval Cinque Ports town of Rye. The inn offers colorful rooms, a rustic pub, and cooked-to-order breakfast for all family members, including furry ones. Originally a warehouse for contraband seized from smugglers, this historic building dates back to 1592. It's an ideal spot to enjoy brunch after exploring Rye Harbour Nature Reserve or to stop for lunch during a day out in town.
Food was amazing and really nice service. The Sunday roast dinner was lovely and hubby’s trout salad was lush. We also had desserts. Not too badly priced for two people.
Billy B — Google review
Really enjoyed the food. Whilst it may be slightly more expensive than normal pub grub. It was much better quality. I had the fish and chips. The tartar sauce was amazing. Dog friendly pub.
Neville S — Google review
A wonderful friendly pub with amazing food . The food is freshly cooked and lots of attention to detail with flavourful food. Dog friendly. A shout out to all the staff but particularly Tom who gave us great attention and even information of things to do locally
Jane D — Google review
Both had belly of pork. Best I have ever had. The whole meal was first class. I don't usually eat the cracklin as it is usually either chewy or too hard. It was perfect, crunchy & tasty. Would highly recommend having a meal here. Staff were all friendly as well.
Peter H — Google review
Excellent food.. Had the steak and half a pint of prawns. Really good. Staff were super pleasant and friendly will visit again. Right next to a car park as well. Happy days!
Spanish C — Google review
My partner and I was looking for somewhere to have a lovely dinner on our last day, we came across the ship inn rye. We ordered the belly pork dinner and wasn't disappointed, it was really good. The portions are small compared to your own dinner at home. I went to pay and left a tip, it was only later that I checked the bill and saw there was a surcharge, but when i offered a tip they never said ive already paid, so be careful when paying the bill
Nigel W — Google review
Lots of empty tables but told by rude staff member they were completely full and we should have booked. Was a Monday night so quiet. We went elsewhere but walked past an hour later and the same tables still empty. Many places much better without the rude staff.
Leisa W — Google review
We went in to book a table The manager(?) told us he only had 2 tables left for 8! So we went odor a quick walk around the town. Unfortunately we actually didn’t eat here. As we sat down and ordered our wine and food, we were informed no more fish & chips. So we left. We ended up in the Standard Inn. Much nicer atmosphere and great fish & chips. Aggrevation at first but in the end we were much better off. Thank you staff @ the Standard Inn, you saved our evening!
Brigitta V — Google review
The, Strand, Rye TN31 7DB, United Kingdom•http://theshipinnrye.com/•+44 1797 229256•Tips and more reviews for The Ship Inn
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What's the weather like in Winchelsea?

It depends on when you visit! We've compiled data from NASA on what the weather is like in Winchelsea for each month of the year: see the links below for more information.

  • Weather in Winchelsea in January
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  • Weather in Winchelsea in October
  • Weather in Winchelsea in November
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All road trips from Winchelsea

  • Winchelsea to London drive
  • Winchelsea to Torquay drive

Explore nearby places

  • Winchelsea
  • Rye
  • Camber
  • Northiam
  • Battle
  • Hastings
  • Bodiam
  • Tenterden
  • Woodchurch
  • New Romney
  • Dungeness
  • Bexhill-on-Sea
  • Dymchurch
  • Sissinghurst
  • Burwash
  • Smarden
  • Goudhurst
  • Ashford
  • Lympne
  • Pevensey
  • Hythe
  • Hailsham
  • Eastbourne
  • Polegate
  • Paddock Wood
  • Leeds
  • Folkestone
  • Yalding
  • Royal Tunbridge Wells
  • Chilham
  • Capel-le-Ferne

All related maps of Winchelsea

  • Map of Winchelsea
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  • Map of Camber
  • Map of Northiam
  • Map of Battle
  • Map of Hastings
  • Map of Bodiam
  • Map of Tenterden
  • Map of Woodchurch
  • Map of New Romney
  • Map of Dungeness
  • Map of Bexhill-on-Sea
  • Map of Dymchurch
  • Map of Sissinghurst
  • Map of Burwash
  • Map of Smarden
  • Map of Goudhurst
  • Map of Ashford
  • Map of Lympne
  • Map of Pevensey
  • Map of Hythe
  • Map of Hailsham
  • Map of Eastbourne
  • Map of Polegate
  • Map of Paddock Wood
  • Map of Leeds
  • Map of Folkestone
  • Map of Yalding
  • Map of Royal Tunbridge Wells
  • Map of Chilham
  • Map of Capel-le-Ferne

Winchelsea throughout the year

  • Winchelsea in January
  • Winchelsea in February
  • Winchelsea in March
  • Winchelsea in April
  • Winchelsea in May
  • Winchelsea in June
  • Winchelsea in July
  • Winchelsea in August
  • Winchelsea in September
  • Winchelsea in October
  • Winchelsea in November
  • Winchelsea in December

Looking for other day-by-day itineraries in Winchelsea?

Check out our other curated itineraries that are also filled with jam-packed days:

  • 1-Day Winchelsea Itinerary
  • 3-Day Winchelsea Itinerary

Day itineraries for nearby cities

  • 2-Day Folkestone Itinerary
  • 2-Day Royal Tunbridge Wells Itinerary
  • 2-Day Hastings Itinerary
  • 2-Day Eastbourne Itinerary
  • 2-Day Ashford Itinerary
  • 2-Day Rye Itinerary
  • 2-Day Hythe Itinerary
  • 2-Day Bexhill-on-Sea Itinerary
  • 2-Day Hailsham Itinerary
  • 2-Day Tenterden Itinerary
  • 2-Day Battle Itinerary
  • 2-Day New Romney Itinerary
  • 2-Day Paddock Wood Itinerary
  • 2-Day Goudhurst Itinerary
  • 2-Day Chilham Itinerary
  • 2-Day Dungeness Itinerary
  • 2-Day Dymchurch Itinerary
  • 2-Day Woodchurch Itinerary
  • 2-Day Polegate Itinerary
  • 2-Day Pevensey Itinerary
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  • 2-Day Burwash Itinerary
  • 2-Day Bodiam Itinerary
  • 2-Day Northiam Itinerary
  • 2-Day Sissinghurst Itinerary
  • 2-Day Capel-le-Ferne Itinerary
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  • 2-Day Leeds Itinerary
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