Rooftop at 1912 Ocean Bar & Rooftop

Love makes you feel on top of the world (or so the saying goes). Maybe that’s why romance rises to the occasion when date night is spent at a rooftop restaurant or bar. With pleasant temperatures and magnificent views, escape the hustle and bustle of St. Augustine’s cobblestone streets by taking things up a notch. That is… all the way up to the best rooftop restaurants and bars in St. Augustine and nearby Jacksonville.

Rooftop Restaurants and Bars in St. Augustine

Not far from the iconic Lion’s Bridge, the following rooftop restaurants and bars in St. Augustine offer bird’s-eye views of The Ancient City.

Casa Reina Taqueria & Tequila

1 Anderson Cir, St. Augustine, FL 32084

Just a stone’s throw from the Lion’s Bridge and Matanzas River, this gem is a top date night destination with rooftop seating, as well as patio and dining room tables. Casa Reina hits all the right notes with splendid scenery, flavorful fare, and affordable date night prices.

Open for lunch and dinner (with separate menus), expect large portions. The Carnitas Platter is a crowd-pleaser. This house-braised pork entrée features caramelized onions, poblanos, red bell peppers, Guajillo BBQ sauce, and crema drizzle, with refried beans and yellow rice.

Aside from signature margaritas, libation lovers can try various tequila and mezcal flights. Plus, Casa Reina has good mojitos and sangria, and non-alcoholic choices like Mexican Cane Sugar Coca-Cola.

Wide exterior shot of Casa Reina
Photo courtesy of Casa Reina Taqueria & Tequila

Milltop Tavern

19 1/2 St. George St., St. Augustine, FL 32084

Built as a gristmill in the 1880s, Milltop Tavern became a rooftop restaurant and bar in the 1950s. To this day, it dominates as a go-to listening room for live music and pub-style munchies.

The rooftop on the backside of Milltop grants views of Castillo de San Marcos National Monument and the Matanzas River. The small patio with bar stools on the opposite side of this historic hideaway overlooks the city’s most popular pedestrian corridor.

Pesca Rooftop

117 Vilano Rd., St. Augustine, FL 32084

Located inside—or should we say on top of—the Hyatt Hotel is one of the most stunning lobby bars. With a backdrop of pristine Vilano Beach, Pesca Rooftop has a lounge menu comprised of Latin and Caribbean infusion.

Signature drinks are often served in vibrant blowfish-shaped glasses. Try the Vilano Vixen, made with locally distilled St. Augustine Vodka, passion fruit, orgeat, lemon, and soda.

Once the sun sets, snag a table inside the dining room. The romantic dinner menu is curated by award-winning chef Michael Lugo. The lobster paella is divine!

Note that Pesca's rooftop hours are Thursday and Friday, 3pm – close and Saturday and Sunday 12pm – close, whereas the lobby and dining room has additional hours.

Pesca's Rooftop
Photo courtesy of Pesca Rooftop

River & Fort

12 Avenida Menendez, St. Augustine, FL 32084

This large, popular eatery has something for everybody. Limited reservations are available for the full-menu dining room and courtyard seating. However, we recommend you take your chances for the first-come, first-serve rooftop spaces.

On both the second and third floors, the rooftop spaces have a pizza kitchen. But with impeccable views, this pizza night is sure to be uber romantic. Try the Filet & Caramelized Onion Neapolitan pizza, paired with either a locally brewed beer, wine, or cocktails. Do save room for the wood-fire baked beignets.

Saint

44 Avenida Menendez, St. Augustine, FL 32084

Saint is a sophisticated yet inviting Italian restaurant known for its elevated cuisine, craft cocktails, and stylish ambiance. Located in the heart of the historic district, Saint blends modern flair with old-world charm, offering both lunch and dinner menus.

One of its standout features is, of course, the rooftop dining area, offering sweeping views of the city’s iconic skyline and a romantic atmosphere that’s perfect for date night or a memorable evening with friends. Whether you're savoring fresh seafood or sipping a signature cocktail under the stars, the rooftop at Saint creates a truly unique experience.

Listen, this place is super tasty so, after feasting on the rooftop, plan to take a long walk down some of St. Augustine's most romantic streets.

Salt Life Food Shack

321 A1A Beach Blvd., St. Augustine Beach, FL 32080

Salt Life has three locations in the Northeast Florida region but the St. Augustine Beach spot undoubtedly tops the Jacksonville Beach and Fernandina Beach restaurants. That’s because it is one of the best rooftop restaurants and bars in St. Augustine.

Directly across from the Atlantic Ocean, feast on raw bar favorites, sushi, street tacos, handhelds, coastal greens, and, my personal fav, loaded poke bowls.

A mid-week date night to Salt Life is a great choice since sushi, edamame, and wine are half-off on Tuesdays and margaritas and oysters are half-off on Thursdays.

Glasses of red and white wine at The Cellar Upstairs
Photo courtesy of The Cellar Upstairs

La Cocina at The Cellar Upstairs

157 King St., St. Augustine, FL 32084

A longstanding destination beloved by locals and visitors alike, the San Sebastian Winery is ever-changing to better serve customers. In 2024, for example, The Cellar Upstairs morphed into La Cocina at The Cellar Upstairs, still presenting a gorgeous rooftop view. You’ll love soaking up the San Sebastian River and its unique marsh, while also taking in live jazz tunes.

Leading the charge is Chef Norberto Jaramillo, who boasts two decades of experience. He's finessed pairing the finest culinary ingredients with exceptional wines. This space now offers multiple menus, including bar, lunch, dinner, and chef's pairing menu.

Consider doing the free wine tasting in the main winery downstairs to discover which vino varieties please your palate. San Sebastian Winery makes reds, whites, rose, sangria, and port, mostly with muscadine grapes harvested in Florida.

The Chop House

330 Pine Lake Drive, Ponte Vedra Beach, FL 32081

Located in the up-and-coming Nocatee neighborhood, The Chop House offers an elevated dining experience—literally and figuratively. This recently-opened, upscale steakhouse features a charming rooftop terrace that provides calming views of preserve lands and a small lake.

Perfect for date nights or special celebrations, couples can enjoy prime cuts of steak, fresh seafood, and expertly crafted cocktails while dining on the rooftop. The Chop House's rooftop ambiance blends elegance with coastal charm, offering both open-air seating and a cozy, inviting vibe. With impeccable service and a refined menu, The Chop House delivers a memorable culinary experience.

1912 Ocean Bar & Rooftop

619 Ponte Vedra Blvd., Ponte Vedra Beach, FL 32082

The highly anticipated 1912 Ocean Bar & Rooftop opened in the summer of 2023 for dinner and drinks; and, then in 2024, introduced Sunday brunch. The restaurant offers amazing views of the Atlantic Ocean with indoor and outdoor seating on the second floor, plus, a comfy rooftop lounge on the third floor.

The menu features flatbreads, salads, seafood, and steaks. This rooftop is best enjoyed on a warm night. Unfortunately, I dined here on a windier evening and felt cold despite the heating lamps.

I also was slightly underwhelmed by the meal my date and I shared at 1912. It was fine but I’d expect better than fine at a fine dining establishment. Still, I wouldn’t hesitate to return again for small plates and cocktails on the rooftop this spring or summer. You just can't be the location!

Cocktail glasses toasting
Photo courtesy of River & Fort

Elevated Patio Seating in St. Augustine

Technically not rooftops, but the following elevated outdoor decks and wrap-around patios boast top-notch views in St. Augustine.

Meehan's exterior boasts water views.
Meehan's Irish Pub | courtesy of Maria DiCicco

Bonus! If you’re dreaming of a rooftop wedding venue, check out The White Room.

Rooftop Restaurants and Bars in Nearby Jacksonville

If and when you’re visiting the other coast, check out amazing rooftop bars in the Tampa Bay area! And, of course, Orlando has its fair share of rooftop bars and restaurants too.

Nancy DeVault is a fitness enthusiast, news junkie, shoe lover, adult beverage fan and travel addict. She works as a Florida-based freelance writer and editor. Nancy is always down for date night, girls night out and family fun adventures.