Curator’s statement
St. Augustine is special to me because it beautifully blends rich history with laid-back coastal charm. As the oldest city in the US, you can feel the stories in the architecture, forts, and cobblestone streets, yet it never feels stuffy or overly formal. I love spending time exploring the nearby federal and state parks, where the beaches, dunes, and wildlife offer a peaceful contrast to the lively energy of downtown. The mix of culture, nature, and that fun, welcoming atmosphere makes it a destination I’m always excited to return to.
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Things to do in St. Augustine
Cold breeze, warm hearts, and a whole lot of ocean therapy.
Visit Castillo de San Marcos
I enjoyed this so much more than I expected to. Standing on the stone walls overlooking the water, you can literally feel the layers of history—it’s powerful, scenic, and completely worth your time.
Take the trolley tour
I always recommend starting with the trolley. It gives you context for everything you’re seeing, helps you get your bearings, and makes the city’s stories come alive in such an engaging way.
Walk the dunes & beach trails
The dunes are my happy place. The mix of palms, oaks, magnolia trees, and sea air feels peaceful and grounding—a beautiful contrast to the energy of downtown.
Wander & shop downtown
Strolling St. George Street and the surrounding blocks is part of the fun. I love popping into boutiques, discovering local art, and just soaking in the lively atmosphere.
Enjoy the food scene
The dining here is part of the experience. From fresh seafood to cozy historic restaurants, every meal feels special—especially if you can snag a water view.
Sunrise on Vilano Beach
If you’re willing to wake up early, this is magic. The beach feels quiet and untouched, and watching the sky change colors over the Atlantic is a peaceful way to start the day.
Explore Anastasia State Park
When I want space and nature, this is where I go. The ancient dunes and maritime forest trails feel serene—it’s hard to believe downtown is just minutes away.
Browse Uptown’s antique & local shops
A little less crowded than the main tourist stretch, Uptown has its own charm. The antique stores and locally owned shops are perfect for slow wandering and unexpected finds.
Waterfront dining at sunset
Ending the day by the water just feels right here. Whether it’s casual seafood or something more elevated, sunset over the marsh or intracoastal never disappoints.
Add a spa or massage afternoon
After a day of cobblestone streets and exploring, a massage or spa stop feels indulgent in the best way—the perfect balance of adventure and relaxation.
Places to eat & drink in St. Augustine
When in Florida… you order the lobster roll. Buttery, messy, completely worth it—and yes, I’d order it again without hesitation. St. Augustine knows how to do seafood right.
The Columbia Restaurant: A classic for a reason. Spanish-inspired dishes, great sangria, and a beautiful old-world atmosphere right in the heart of downtown.
Caps on the Water: If you can get in, go. Casual seafood, palm trees, and sunset views over the intracoastal—it’s the kind of Florida dining experience people picture in their heads.
The Floridian: Fresh, local, and Southern-inspired with a creative twist. It feels cozy and thoughtful—perfect when you want something authentic and not overly touristy.
Ice Plant Bar: Craft cocktails done right. The vibe is industrial-chic, the drinks are elevated, and it’s a fun stop before or after dinner.
Harry’s Seafood Bar & Grille: A lively spot with New Orleans flair. Great for Cajun flavors, outdoor seating, and people-watching in the heart of the action.
Raintree Restaurant: Romantic and charming, especially in the courtyard. It’s a wonderful option for a slower, more intimate dinner.
Beachcomber Restaurant (Anastasia Island): Toes-in-the-sand casual with solid seafood and cocktails. It’s relaxed, unpretentious, and perfect after a beach walk.
Prohibition Kitchen: A fun, energetic atmosphere with live music and elevated comfort food. Great for a lively evening out.
Forgotten Tonic: Creative, beautifully plated dishes and excellent cocktails. It’s one of those places that feels trendy but still approachable.
St. Augustine Distillery: A great daytime stop to sample local spirits and learn a little history. It’s interactive, fun, and a nice break from walking.
Need to know
It’s more walkable than you think. Downtown is compact and very walkable, but the streets are brick and cobblestone—comfortable shoes are a must.
Weather can surprise you. Even in Florida, winter can feel chilly (especially with ocean wind). Bring layers—you may want a light jacket in the morning and sunscreen by afternoon.
Parking takes patience. If you’re staying outside of downtown, plan ahead for parking. The trolley is a great way to avoid stress.
Make dinner reservations—especially on weekends. The best waterfront and historic spots fill up quickly.
Balance history with nature. Don’t just stay downtown. The beaches, Anastasia State Park, and Vilano offer a peaceful contrast and are absolutely worth your time.
It’s busy during peak seasons. Spring break and holiday weekends bring crowds. If you prefer a quieter experience, consider shoulder season travel.
Sunrise > Sunset (Sometimes!). Everyone talks about sunset—but sunrise on the beach is often quieter and just as beautiful.
Travel Advisor
Susie Pryfogle
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