Things To Do
Activities & Site Seeing:
Tour of Flagler College
Flagler College Historic Tour – Caroline’s Alma Mater! Explore one of St. Augustine’s most breathtaking landmarks with a guided tour of Flagler College’s historic campus. Once the opulent Hotel Ponce de Leon, this stunning Spanish Renaissance building now serves as a college and showcases extraordinary architecture, Tiffany-stained glass windows, hand-carved wood details, and rich Gilded Age history. Tours depart daily from the Rotunda on King Street and last about 45-60 minutes — a must-see for history, architecture, and St. Augustine culture lovers.
Saint George Street
Historic St. George Street is the heart of the Historic District in St. Augustine, Florida, and one of the city’s most iconic and walkable landmarks. It’s a pedestrian-only street that follows a roadbed first laid out in the 1700s. Enjoy local shops, restaurants, and more!
Castillo de San Marcos National Monument
The Castillo De San Marcos is a 17th-Century masonry fort in St. Augustine, Florida, built by Spain to defend its New World claims. It is the oldest masonry fortification in the continental United States and a key symbol of early European colonial power in North America. Fun Fact: this is where we got engaged!
St. Augustine Beach Pier
Catch a sunset at the pier or relax at the beach!
Lightner Museum
The Lightner Museum is a historic museum and cultural landmark located in the heart of downtown St. Augustine, Florida. It occupies the former Hotel Alcazar, a grand Gilded Age resort built in 1888 by industrialist Henry Flagler. The museum showcases art, decorative objects, and artifacts reflecting both local and global heritage.
The Oldest House
The Oldest House Museum, also known as the González-Alvarez House, is a historic museum complex in St. Augustine, Florida. Operated by the St. Augustine Historical Society, it preserves Florida’s oldest surviving Spanish colonial dwelling and offers an immersive experience of the region’s layered history spanning more than three centuries.
Aviles Street
Aviles Street is a famous historic street in St. Augustine, Florida — one of the city’s most iconic and charming locations. It’s widely recognized as the oldest street in the United States and is a major highlight of the city’s historic downtown area. Aviles Street is a walkable, pedestrian-friendly corridor lined with: Art galleries and artisan studios, Boutique shops and antique stores Cafés, wine bars, and restaurants, Public art and murals that celebrate local culture.
Old Town Trolley Tours St Augustine
Iconic hop-on/hop-off tour of historic St. Augustine. The perfect way to explore major sites like the historic downtown, Castillo de San Marcos, and more at your own pace.
Saint Augustine Distillery
St. Augustine Distillery is a craft distillery in St. Augustine, Florida, known for its award-winning, farm-to-bottle spirits like bourbon, rum, gin, and vodka, made from local ingredients. Located in a restored historic ice plant, it offers free tours and tastings daily, showcasing its production process and history, and is adjacent to the farm-to-table Ice Plant restaurant. Take a self-guided tour, which includes multiple spirit tasting opportunities or - for the true spirit-enthusiast, book an in-depth, educational guided tour and tasting experience.
San Sebastian Winery
San Sebastian Winery is one of Florida’s premier wineries, known for producing a wide range of award-winning wines — including table wines, sparkling wines, and dessert styles — with a focus on both Vinifera varieties (like Chardonnay and Cabernet Sauvignon) and native Muscadine grapes. The winery has earned hundreds of awards for its wines over the years. The winery is located at 157 King Street in a restored Henry Flagler East Coast Railway building just a few blocks from historic downtown St. Augustine. Its location pays homage to the area’s deep history — St. Augustine is often associated with early American wine history. Winery tours and tastings are offered seven days a week. You can enjoy guided and self-guided tours, which usually include a short audio-visual presentation about winemaking and an opportunity to sample several wines. Tastings are available for adults (21+) and the gift shop features bottles, wine accessories, gourmet foods, and customizable gift baskets.
St. Augustine Alligator Farm Zoological Park
The Alligator Farm Zoological Park is a historic wildlife park and zoo located on Anastasia Island (about 1.5 miles from the Bridge of Lions). It’s been operating since 1893, making it one of Florida’s oldest continuously running attractions. It’s best known for its collection of crocodilians and reptiles, but it’s much more than just alligators – it’s a full zoological experience with many species of animals, birds, and educational exhibits. Fun Fact: this is Anthony’s favorite attraction in St. Augustine!
St. Augustine Lighthouse & Maritime Museum
The St. Augustine Lighthouse & Maritime Museum is a historic 1874 lighthouse on Anastasia Island offering some of the best panoramic views in the city. Guests can climb 219 steps to the top and explore maritime exhibits, shipwreck artifacts, and the restored keeper’s house. It’s a scenic, photo-worthy stop that blends coastal history with beautiful waterfront views.
Coffee Shops:
The Kookaburra Downtown
The Kookaburra Downtown is a beloved Aussie‑American coffee shop in St. Augustine, known for its freshly roasted coffee, creative espresso drinks, and Australian‑inspired pies and pastries. The café began in downtown St. Augustine in 2012 and has since grown into a local favorite with multiple locations across the area, serving everything from honey‑spiced lattes to savory “Aussie lunch pies.”
Relámpago Coffee Lab
Relampago Coffee Lab is a specialty coffee shop and café known for its high‑quality, freshly roasted beans and carefully brewed espresso drinks. The name Relámpago means “lightning” in Spanish, and the café is focused on bold, flavorful coffee experiences in a relaxed setting.
Bars:
The Tini Martini Bar
Tini Martini Bar is a cozy martini‑focused cocktail bar in historic downtown St. Augustine, located on the bayfront at the Casablanca Inn with outdoor seating and views over Matanzas Bay. It’s known for its creative specialty martinis and classic cocktails, a relaxed vibe, and live jazz or blues music on weekend nights — perfect for sipping and socializing after dinner. 🌅🍸 And fun fact: it’s Caroline’s absolute favorite bar in St. Augustine!
Stogies Jazz Club & Listening
Stogies is a jazz club, cigar lounge, and nightlife venue in historic downtown St. Augustine, known for its relaxed, old‑city atmosphere, daily live music, and extensive drink and cigar selection.
The Backyard at Meehan's
The Backyard at Meehan’s is a casual outdoor dining and bar space located just behind the main Meehan’s pub. It’s set up like a tropical courtyard and patio area with a laid‑back vibe — a nice alternative to the traditional Irish pub interior.
Scarlett O'Hara's
Scarlett O’Hara’s was a longtime pub and grill in the heart of historic downtown St. Augustine, known for its laid‑back vibe, drinks, pub food, and live music. It had indoor and outdoor bar areas, a front porch, and a reputation as a favorite hangout for locals and visitors alike over many years.
Odd Birds Cocktail Lounge and Kitchen
Odd Birds is a craft cocktail lounge and full‑service restaurant with a vibrant, eclectic atmosphere blending Latin‑inspired cuisine and small‑batch, creative drinks.
Restaurants:
Purple Olive Restaurant & Catering
Purple Olive Restaurant & Catering is a well-loved, chef-driven restaurant on Anastasia Boulevard in St. Augustine, FL, known for its fresh, eclectic dinner menu with Mediterranean-inspired and American dishes. (Reservations Recommended)
Forgotten Tonic
Forgotten Tonic is a popular New-American restaurant and cocktail bar tucked away on historic Aviles Street in downtown St. Augustine. It’s known for its creative handcrafted cocktails, extensive wine list, and a menu of elevated comfort dishes — from shareable appetizers to hearty mains — all served in a stylish yet relaxed setting. (Reservations Recommended)
Ice Plant Bar
Ice Plant Bar (also known simply as The Ice Plant) is a standout restaurant and cocktail bar in St. Augustine’s historic downtown, housed in a beautifully restored 1920s industrial ice factory that once made ice for the local fishing industry. Today it’s known for its craft cocktails — often featuring house‑pressed juices, artisanal syrups, and precisely curated ice — along with a farm‑to‑table menu that includes local seafood, grass‑fed meats, vegetarian options, and daily specials served in a vintage‑industrial setting.
Catch 27
Catch 27 is a well‑liked seafood restaurant and cocktail spot in the heart of historic St. Augustine’s downtown, known for its fresh, locally caught Florida seafood and seasonal, scratch‑made dishes. Caroline’s personal favorite! Its menu blends Southern charm with coastal flair — think seafood entrees, inventive appetizers, house‑made sides, and creative cocktails — and it offers both intimate indoor seating and a relaxed outdoor courtyard. (Reservations Recommended)
Blackfly The Restaurant
Blackfly The Restaurant is a beloved, coastal‑focused restaurant on Anastasia Island just over the Bridge of Lions in St. Augustine. It’s known for its fresh, locally sourced seafood, creative surf & turf dishes, brick‑oven pizzas, and an extensive wine and cocktail selection, all served in a lively yet relaxed setting that blends casual comfort with sophisticated flavors. (Reservations Recommended)
St. Augustine Fish Camp
St. Augustine Fish Camp is a popular seafood restaurant right on the waterfront in downtown St. Augustine’s Lincolnville neighborhood, known for its fresh coastal dishes, laid‑back vibe, and beautiful views of the San Sebastian River. The menu features a mix of classic and creative seafood — from oysters and shrimp to grilled fish, clam bellies, and signature shrimp & grits — plus handcrafted cocktails and a welcoming outdoor dining area perfect for sunset dinners.
Burrito Works Taco Shop
Burrito Works Taco Shop – A longtime local favorite right on St. George Street in historic downtown St. Augustine with a casual, laid‑back vibe and Baja‑Mex flavors. They’re especially known for their customizable tacos, burritos, nachos, and their signature UFO (a taco/burrito/quesadilla hybrid). Open until around 2 AM on weekend nights.
Mojo Old City BBQ
Mojo Old City BBQ is a laid‑back barbecue and Southern cuisine spot blending flavors from different regional barbecue traditions. It’s part of the larger Mojo BBQ family, which has multiple locations throughout North and Central Florida.
Cap's On the Water
Cap’s On the Water is a waterfront restaurant and bar located right on the Intracoastal Waterway in St. Augustine’s Vilano Beach area. It’s famous locally for its scenic views, especially at sunset, and its laid‑back but polished coastal vibe perfect for a meal with a view.
The Reef
The Reef is one of St. Augustine’s most iconic oceanfront restaurants, located right on the Atlantic Ocean at North Beach/Vilano Beach — about three miles north of downtown. It’s especially known for spectacular water views, creative seafood cuisine, and a relaxed yet refined coastal vibe.
Beaches at Vilano
Beaches at Vilano is a laid‑back waterfront restaurant and bar right on the Tolomato River near Vilano Beach. It’s known for its Caribbean‑inspired, seafood‑forward menu, scenic water views, and relaxed, beachy vibe — a favorite local hangout that feels like a little tropical escape just minutes from downtown.
Aunt Kates
Aunt Kate’s is a family‑run, historic seafood restaurant sitting right on the Tolomato River in Vilano Beach. It’s been serving locals and visitors for over 100 years with a focus on fresh, coastal Florida flavors and a relaxed, scenic atmosphere.