If you're looking for a way to see most of the recommendations on this list, purchase a one-day ticket for around $35 per person to ride on the Old Town Trolley Tour! It takes you throughout the city of St. Augustine and allows you to check out the sites while listening to the tour guide explain the history of it all.
Jared and Emma first visited the fort together just about a week before Jared bought the engagement ring in August of 2024! The standard pass required for general entry is $15 per person and free for active duty military and veterans (you just have to ask). They don't accept cash here, so don't forget your credit cards! This historical location accepts walk-ins and is completely self-guided and paced.
This distillery offers free tastings and tours 7 days per week for anyone over the age of 21 and includes a taste of vodka, rum, whiskey, and more! Located on top of the distillery is Ice Plant Bar, open for brunch, lunch, and dinner.
If the weather allows, take a walk through downtown St. Augustine! There are plenty of shops, bars, restaurants, and historic locations along the way.
Enjoy some food and drinks with a view of the river and the fort (hence the name) at this St. Augustine staple!
This location is a little further out of downtown but offers indoor and outdoor seating, great food and drinks, and live music.