St Augustine is super cute in the historic district. They have a bunch of cute little shops. You can check out the fort, and there's a super old school house. Orlando has a ton of things to choose from, depends on what you're interested in and your price range.

Harry's for sure, it's a little nicer and it's fantastic. Maybe Conch House (I think they're still around) for a cool over the water dining experience.

I love the Floridian, Burrito Works and the Ice Plant, but there are so many good ones! Here’s some more recommendations on my blog https://thefloridatravelgirl.com/best-st-augustine-restaurants/

For the first half, St Augustine has some AMAZING sunset cruises on private sailboats ♥️ Congratulations!

We went to St. Augustine last minute so couldn’t find any reasonable priced hotels on the beach so stayed at the Courtyard across the beach. Check out the Embassy Suites which was right on the beach. The property was very nice from the beach.