Things To Do
Castillo de San Marcos National Monument
This centuries-old fort has stood watch over the bay since the 1600s, and it’s also where Brian asked Alaina to be his girlfriend AND where he popped the question! It’s full of history, but for us, it’ll always be part of our love story.
Lightner Museum
Once a grand hotel, now a museum filled with antiques, and a dreamy courtyard. It’s romantic and peaceful.
Flagler College
Originally built as a luxury hotel in the 1800s, now one of the most beautiful college campuses in the country. Brian went to school here, so it’s extra special to us. The courtyard and architecture are worth seeing, even just for a quick stroll.
Ponce de Leon's Fountain of Youth Archaeological Park
A whimsical little park where peacocks wander. The spring is said to grant eternal youth, worth a sip, just in case!
Old Town Trolley Tours St Augustine
This hop-on, hop-off trolley is a fun and easy way to see the city. Great for first-timers or if you just want to cruise around and learn a little along the way.
Ghost & Gravestones Ghost Tour
A spooky trolley tour that’s part history, part spooky. Alaina’s mom & stepdad love ghost tours, so if you’re into the supernatural, this one’s a must.
St. Augustine Lighthouse & Maritime Museum
Climb the 219 steps for one of the most stunning views in town. The lighthouse is iconic, peaceful, and a little spooky (in the best way).
San Sebastian Winery
Tastings, rooftop music, and local wine? Yes, please. This is an easy afternoon favorite.
City Gate Spirits
Right by the old city gates, this spot offers fun (and strong) spirit tastings. A great stop to sip something new and locally made!
No Name Bar
A dive bar with a view. Right across from the fort, this bar has live music almost every night and a great mix of locals and visitors. Alaina bartended here for years, so it’s close to our hearts. Always a fun stop if you want a drink, some good people-watching, or to just say hi to some of our friends!
The Tini Martini Bar
Our go-to date night spot for cocktails. Cozy, romantic, and right on the bayfront with a great view.
Auggie's Draft Room
Pour-your-own beer wall, rotating taps, and a relaxed atmosphere make this a fun spot to try something new.
Sarbez!
Grilled cheese + arcade games = a match made in heaven. This funky little bar is great for grabbing a beer and embracing your inner kid.
Mojo's Tacos
Where it all began. Our first date was here, over tacos and queso. Safe to say we recommend the vibe and the food.
Beaches at Vilano
One of Brian’s favorites! Great food, water views, and a breezy, relaxed vibe. It’s the perfect spot for a casual lunch or dinner by the water.
Ice Plant Bar
Inside the old ice factory, Ice Plant is known for incredible cocktails and great food. It’s one of our picks for a fancy dinner or date night.
Barley Republic
Irish pub with the best chicken tenders. Bonus: they carry Alaina’s favorite beer, Collective Arts Guava Gose. We also went here for dinner right after the proposal, so obviously, we love it here!
River & Fort Restaurant & Roof Top Lounge
Come for the rooftop views, stay for the cocktails. One of the best sunset spots in town. We had drinks here right before he proposed! You can also see where it all happened from the rooftop!
The Backyard at Meehan's
Hidden behind an Irish pub, this outdoor bar is relaxed and perfect for a laid-back drink.
Harry's Seafood, Bar & Grille
A romantic courtyard and dishes with a Southern twist. This was Alaina’s mom & stepdad’s first date spot, so it holds a special place in our hearts.
Saint George Street
The heartbeat of downtown! Filled with shops, music, food, and endless charm.
Aviles Street
The oldest street in the U.S., and one of the quietest corners of downtown. It’s lined with art galleries, local shops, and hidden gems that make it worth a walk through.
St. Augustine Beach
Wide, peaceful, and beautiful! Perfect for a morning walk, an afternoon swim, or a sunset you won’t forget.
Vilano Beach
A quiet beach across the Vilano bridge. Great for escaping the crowds.