Fun Things to Do in St Augustine for Couples: 12 Date Ideas

Picture winding cobblestone streets, centuries-old architecture, and a laid-back vibe that’ll have you strolling hand in hand, ice cream cones in tow, all day long. Whether you’re scouting for the perfect date night spot, looking for free things to do in St Augustine for couples, or simply hoping to impress your sweetheart with a little historically inclined flair, you’ve got options. From the historic district to the sweeping views at the St Augustine Lighthouse, this city is brimming with opportunities to spark some romance.

Without further ado, here are 12 epic—yet charmingly low-key—things to do in St. Augustine for couples, guaranteed to set the mood for a getaway you’ll never forget.

1. Stroll the Beaches at Sunrise

One of the most fun things to do in St Augustine for couples is to start the day with the ultimate coastal cliché: walking hand in hand on a near-empty shoreline as the sun slowly peeks over the Atlantic. Augustine Beach is a local favorite, offering miles of soft sand and gentle waves perfect for wading.

If you’re both early risers, greet the day at Vilano Beach, where the pastel hues of morning stretch across a tranquil seascape. Better yet, this romantic escapade won’t cost you a dime—making it one of the best free things to do in St. Augustine for couples. It’s just the two of you, the sound of the surf, and maybe a few seagulls eavesdropping on your whispered plans for the day.

2. Wander Through the Historic District & Take a Carriage Ride

The heart of the city is the historic district, and it’s practically begging to be discovered slowly, step by step, at your side. Lose yourselves amid the centuries-old streets and admire the intricate Spanish Colonial architecture.

For a true old-world treat, hop into a carriage ride through the historic neighborhoods at dusk, when the gas lanterns cast a warm glow on the cobblestones. You’ll feel like you’ve been transported back in time—just without the funny hats (though feel free to buy one from a local shop for flair). As you pass by landmarks like the Bridge of Lions, you’ll realize this city was practically built for romance.

3. Explore the Lightner Museum & Flagler College

If your style of romance includes a dash of culture, then plan on spending a morning at the Lightner Museum, housed in the former Alcazar Hotel built by railroad tycoon Henry Flagler. Inside, you’ll find an eclectic collection of fine and decorative arts that set the stage for intriguing conversations—because who doesn’t love a little debate over which Victorian vase is the prettiest?

Afterward, wander over to the regal campus of Flagler College, another Flagler masterpiece. Marvel at the Tiffany stained glass, ornate ceilings, and perfectly manicured courtyards. It’s a setting that might just inspire you to call each other “darling” a little more than usual.

4. Sip From the Fountain of Youth

Legends say that if you drink from the Fountain of Youth, located at the Fountain of Youth Archaeological Park, 11 Magnolia Ave, you’ll gain eternal youth. Sure, it’s more of a fun myth than a scientifically backed fact, but why not give it a try?

The park itself is steeped in history and natural beauty. Stroll through the lush grounds, watch the resident peacocks strut their stuff, and imagine yourself as a time traveler soaking up the essence of the Ancient City. Even if the water doesn’t shave a few years off your life, the laughter and the memory of this quirky experience are guaranteed to keep you feeling young at heart.

5. Toast to Your Love at San Sebastian Winery’s Cellar Upstairs

For couples who appreciate a good vintage, a visit to the San Sebastian Winery at 157 King St is a must. Wander through the facility on a guided tour to learn about the winemaking process—swirl, sniff, and sip to your heart’s content.

Then make your way up to The Cellar Upstairs for a rooftop experience like no other. From this vantage point, you can enjoy panoramic views of the skyline while savoring a glass of local wine paired with light bites. Often, there’s live music to set the mood, and as you clink glasses under the Florida sun, don’t be surprised if the moment feels straight out of a romance novel.

6. Meander Along St. George Street & Find Your Perfect Date Night Spot

If you’re looking for things to do in St. Augustine for couples that combine history, shopping, and cuisine, St George Street hits the trifecta. This pedestrian-only thoroughfare cuts right through the old town, offering a blend of boutiques, galleries, and tasty eateries. Wander in and out of artisan shops, sample local treats, and maybe pick up a trinket to remember your trip.

As evening approaches, linger over candlelit dinners at cozy bistros or enjoy a date night at a charming wine bar. Don’t rush—St. George Street is best savored slowly, relishing the atmosphere and each other’s company.

7. Indulge in a Chocolate Tour

For those who believe that chocolate is the way to anyone’s heart, this one’s for you. Sign up for a guided chocolate tour at one of the city’s local chocolatiers. As you learn about the bean-to-bar process, you’ll get to nibble on samples that range from velvety truffles to decadent fudge. Chocolate tastings are just so much better when you can share reactions with someone you love.

By the end, you’ll have a newfound appreciation for the confection—and maybe an armful of sweet souvenirs to take home. It’s the kind of fun thing to do in St. Augustine for couples that ends on a richly satisfying note.

8. Discover the Castillo de San Marcos

It wouldn’t be a trip to St. Augustine without a visit to the Castillo de San Marcos, the oldest masonry fort in the continental U.S. Made from coquina (seashell-based limestone), the fortress has stood guard over the waterfront for centuries. Roam its bastions, peer through the ancient cannons, and soak up the panoramic views of the bay. It’s easy to imagine yourselves as adventurers stepping back into the days of pirates and Spanish colonists.

If you time your visit right, you might even catch a historical weapons demonstration. Together, listen to the sound of a 300-year-old cannon going off.

9. Explore the Matanzas National Estuarine Research Reserve

If you’re both nature enthusiasts looking for free things to do in St. Augustine for couples, head south of town to the Matanzas National Estuarine Research Reserve. This protected habitat is bursting with wildlife, salt marshes, and maritime hammocks.

Lace-up your sneakers and set off on one of the walking trails, or rent a kayak and paddle through calm, scenic waters. Keep your eyes peeled for dolphins, manatees, and countless bird species. Breathing in the fresh air and sharing quiet moments in nature will leave you both recharged and ready for whatever adventure comes next.

10. Enjoy Live Music and Nightlife in the Historic District

When the sun sets, St. Augustine’s nightlife scene awakens with a mellow vibe. The historic district offers plenty of cozy corners and outdoor patios where you can settle in for some live music. Grab a table at a local craft beer taproom or wine bar, and sway gently to the tunes of a local jazz trio or acoustic guitarist.

The city’s musical offerings run the gamut, so you’re bound to find something that suits your tastes. Plus, as the evening lights twinkle above, it’s hard not to feel a sense of intimacy and contentment sitting side by side, sipping and swaying in perfect harmony.

11. Stay in a Charming Bed and Breakfast

Last but certainly not least, cement your couples’ retreat by booking a night at a delightful bed and breakfast tucked away in a historic home. These cozy inns often boast antique furnishings, wraparound porches, and friendly hosts who serve up home-cooked breakfasts that’ll put your standard scrambled eggs to shame.

Some are steps away from the city’s most iconic landmarks—imagine waking up and strolling over to the Bridge of Lions before the crowds roll in. Others are nestled near quiet corners of the old town, perfect for couples who want a private hideaway. Either way, a B&B stay adds a personal, romantic touch to your St. Augustine adventure.

12. Climb the St. Augustine Lighthouse

For a literal high point in your relationship, scale the 219 steps of the St. Augustine Lighthouse and Maritime Museum at 100 Red Cox D. Yes, it’s a bit of a climb, but think of it as a couple’s fitness challenge with a truly breathtaking payoff.

Once you reach the top, you’ll be rewarded with sweeping views of the coastline and the city’s rooftops. The breezes will cool your exertion-flushed faces as you snap a few selfies—just try not to drop your phone.

Afterward, explore the keeper’s house and exhibits. This experience is a gentle reminder that, together, you can rise to new heights—both literally and metaphorically.

Bonus Tip: Embrace the Car-Free Lifestyle

Part of the city’s charm is its walkability. Between browsing St. George Street, exploring the Lightner Museum, marveling at Flagler College, and sipping wine at the San Sebastian Winery, you’ll quickly realize that St. Augustine’s main attractions are all just a pleasant stroll (or short ride) away.

You can roam the historic district for free things to do in St. Augustine for couples, like window shopping, street performances, and people-watching—all without spending a cent on transportation. Treat yourselves by leaving the car behind and discovering the city on foot, on a scooter, or bike.

Slowing down is part of the St. Augustine experience, and there’s no better way to savor these romantic moments than keeping pace with each other.

Ready for a St. Augustine Romantic Adventure?

When it comes to things to do in St. Augustine for couples, this coastal gem delivers the goods. From scenic beaches and historic tours to mouthwatering chocolates and fine wine, the Ancient City offers a buffet of experiences for every pair.

Savor a sunrise stroll at Augustine Beach, raise a toast at the Cellar Upstairs, pose against the grandeur of the Castillo de San Marcos, delight in a sweet chocolate tour, or embark on a carriage ride through the historic heart of town. With each shared adventure, you’ll find yourselves weaving a tapestry of memories that will long outlast any postcard or souvenir.

And guess what? Not everything requires a lavish budget. There are plenty of budget-friendly and free things to do in St. Augustine for couples, from wandering the historic district to exploring Matanzas National Estuarine Research Reserve, that won’t cost a dime and still leave you feeling connected and inspired.

So pack your bags, grab your sweetheart’s hand, and get ready for a legendary date night (or two, or three). Romance practically drips from the city’s old wooden balconies, winds around the coquina walls of its storied forts, and lingers in the salty coastal air.