You know that feeling when you’re planning something special for Valentine’s Day, scrolling through the same tired restaurant suggestions and generic date ideas? St. Augustine doesn’t do generic. While other cities might offer you a prix fixe menu at a chain restaurant overlooking a parking lot, this city delivers centuries of atmosphere, hidden courtyards, and sunsets that look like they were painted just for you and your person.
Whether you’re celebrating your first Valentine’s Day together or your fiftieth, we’ve rounded up the most swoon-worthy spots in the Old City that’ll make Valentines Week feel like the opening scenes of your favorite love story. These aren’t just places to visit. They’re backdrops for the kind of moments you’ll be looking back on fondly for years to come.
Climb to New Heights at the St. Augustine Lighthouse
Nothing says “I love you” quite like huffing and puffing together up 219 steps, right? But hear us out. The St. Augustine Lighthouse & Maritime Museum at 100 Red Cox Drive isn’t just about the workout. It’s about what happens when you reach the top, slightly breathless, and see the entire coastline spreading out before you like a watercolor painting. The Atlantic glitters to the east. Downtown St. Augustine unfolds to the west. And somewhere between catching your breath and taking in the view, you’ll probably steal a kiss at 165 feet above sea level.
The lighthouse is open daily from 9:00 AM to 6:00 PM. Morning light is softer and perfect for photos, while late afternoon brings golden hour. After you descend, explore the keeper’s house and maritime hammock nature trails. Book tickets in advance during Valentine’s week, and bring a light jacket for the breezy observation deck.
Sip and Savor at San Sebastian Winery
Wine and romance have been going steady since, well, forever. At San Sebastian Winery (157 King Street), they’ve perfected the art of both. Founded in 1996 in one of Henry Flagler’s original East Coast Railway buildings, this spot has racked up over 957 awards for their wines made from Muscadine and hybrid grapes. But you’re not here for the statistics. You’re here for the experience.
The complimentary tours run every 20-25 minutes from 10:00 AM to 5:00 PM Monday through Saturday, and 11:00
AM to 5:00 PM on Sundays. You’ll learn about the wine-making process, sure, but more importantly, you’ll sample wines together and discover which ones make you both say “oh, THAT’S good.” Maybe it’s the Blanc Du Bois. Maybe it’s the Cream Sherry. Either way, you’re discovering something new together.
After the tasting, head up to La Cocina at the Cellar Upstairs on the third floor. This rooftop restaurant serves international cuisine Tuesday through Sunday from 11:00 AM to 9:00 PM, and the views of St. Augustine’s skyline are the kind that make you forget to look at your phone. The open-air deck is especially lovely when the weather cooperates, which in mid-February usually means comfortable temperatures and gentle breezes. Pair your meal with a bottle of something you discovered downstairs.
Check out what’s happening at the winery during Valentine’s week, as they often feature special tastings or events. Even if you’re not big wine enthusiasts, the setting alone is worth the visit.
Find Your Sunset at Vilano Beach Pier
Forget everything you think you know about beach sunsets. The Vilano Beach Pier flips the script entirely. While most Florida beaches give you sunrise over the ocean, this spot north of downtown lets you watch the sun set over the water, specifically over the Matanzas River with downtown St. Augustine in the distance. The Castillo de San Marcos. The Mission of Nombre de Dios cross. The city skyline catching the last rays of the day. It’s the kind of view that makes you understand why people write love songs.
The pier is open 24 hours with free parking, which means you can show up whenever the mood strikes. But for Valentine’s Day week, time your arrival for about 30 minutes before sunset. Grab one of the two-seater swings (yes, they have swings on the pier), and just settle in. The Art Deco touches, the blue mosaic artwork in the pavilion, even the dolphin statues perched above the water all add to the charm.
If you’re feeling ambitious, make a whole evening of it. Walk the beach first, maybe do that barefoot stroll through the sand that everyone secretly loves but pretends is cliche. Then head to the pier as the light starts to change. Stay until the sky turns that impossible shade of pink-purple-orange that only seems to exist in Florida. And if you’re hungry afterward, Cap’s on the Water is nearby with waterfront dining that’ll keep the romantic momentum going.
Dine Like You Mean It
St. Augustine’s restaurant scene could fill an entire article on its own, but a few spots stand out for Valentine’s Day romance. Collage Restaurant at 60 Hypolita Street serves globally-inspired cuisine in a European-style atmosphere that practically demands candlelight and meaningful conversation. The seasonal menu means you’re getting the freshest ingredients, and the small size means reservations are absolutely essential during Valentine’s week. Think of it as the kind of place where you linger over every course and barely notice two hours have passed.
For something with a French accent, The Drunken Horse offers authentic French cuisine in a setting that feels like you’ve been transported to a Parisian bistro. The courtyard walls create an intimate atmosphere even though you’re in the heart of a busy area, and the music selection leans French, which somehow makes even casual conversation feel more romantic.
If you want waterfront views with your meal, The Reef and Cap’s on the Water both deliver fresh seafood with scenery that doesn’t quit. These spots are a bit more casual but no less special, particularly if you snag outdoor seating. No matter where you choose to dine during Valentine’s week, make reservations now. The popular spots fill up faster than you’d think.
Don’t Miss the Love Tree
Before you leave the historic district, make a pilgrimage to the Love Tree at 6 Cordova Street.
This isn’t just any tree. It’s actually two trees, a sabal palm growing straight out of the heart of an oak, so tightly intertwined that separating them would kill both. Legend has it that a couple planted these trees side by side as a symbol of their devotion, and now locals believe that a kiss in front of the Love Tree will seal two hearts forever.
It’s free, it’s a little bit magical, and it makes for a great story when people ask about your Valentine’s Day plans.
Take a Romantic Carriage Ride
Sometimes the best way to see St. Augustine is from the seat of a horse-drawn carriage, clip-clopping down brick streets while someone else handles the navigation. Several companies offer carriage rides through the historic district, and they’re exactly as romantic as you’d imagine. You’ll pass centuries-old landmarks, hear stories about the city’s past, and have about 45 minutes where your only job is to sit close and enjoy the ride.
Companies like Coastal Carriages and Country Carriages operate daily tours that wind through downtown, showcasing the architecture and atmosphere that makes this city special. For Valentine’s week, consider booking a private carriage for just the two of you. Most tours accommodate up to four or six passengers, but having the carriage to yourselves adds an extra layer of intimacy. Some companies even offer wine packages if you want to add a toast to your tour.
The rides work in any weather (they provide blankets when it’s cool), and they’re particularly magical in the evening when the city takes on a softer glow. Book ahead during Valentine’s week, as these fill up quickly.
The Details That Matter
Valentine’s Day in St. Augustine can feel like you’ve stepped into a different era, which is precisely the point. A few practical notes:
- Weather in mid-February typically runs between 55°F and 72°F. Perfect for walking around, sometimes requiring a light jacket in the evening.
- Parking in the historic district can be tricky. Consider parking at the St. Augustine Visitors Center and taking the trolley into downtown.
- Many restaurants and attractions offer Valentine’s Day specials during February 10-14. Check the Old City calendar for the most up-to-date event listings.
Making It Your Own
The spots we’ve covered are tried and true for a reason. They deliver. But the best Valentine’s Day experience in St. Augustine is the one you create yourselves. Maybe that means ducking into The Ancient Olive on St. George Street to sample olive oils and balsamic vinegars together. Maybe it’s booking a ghost tour because you both love a good scare and holding hands in the dark. Maybe it’s simply finding a quiet bench in the Plaza de la Constitución and watching people go by while sharing a bag of something sweet from Kilwin’s.
The beauty of Old City is that it rewards curiosity. Take a wrong turn down Aviles Street and discover a tiny courtyard you’d never have found otherwise. Follow the sound of live music and end up at a bar you weren’t planning to visit. Buy flowers from a street vendor not because it’s Valentine’s Day and you’re supposed to, but because they caught your eye and you wanted to see your person smile.
St. Augustine has been hosting love stories for more than 450 years. Couples have walked these streets through every conceivable era, wearing every imaginable style. But the essentials haven’t changed. Good food. Beautiful views. The chance to slow down and remember why you chose each other in the first place.
This Valentine’s Week, Old City is ready for your chapter. The lighthouse is waiting. The wine is breathing. The sunset over Vilano Beach Pier is warming up for its nightly performance. All that’s missing is you two, ready to add your own story to the ongoing romance of America’s oldest city.
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