12 Dreamy Things to Do in St Augustine for Couples (That Aren’t Just Candlelit Dinners)
Planning a romantic getaway that’s equal parts charming and exciting can feel like a lot. But St. Augustine gets it right with old-world architecture, sunset sails, and candlelit restaurants made for lingering conversations.
Couples looking for more than the usual dinner-and-a-movie will love how this coastal city blends history, beauty, and spontaneity.
From wine tours to waterfront walks, there’s no shortage of fun things to do in St. Augustine for couples who want to make their trip feel special.
Whether it’s your first weekend away or your fiftieth, you’ll find unique experiences to match any couple’s vibe.
These are the most unforgettable things to do in St. Augustine for couples, and they’re too good to miss!
St. Augustine-Style Romance: Cruises, Carriages & Boozy Tours to Fall For
Carriage Rides
Clip-clop your way through romance with a cozy ride from Country Carriages, Old City Carriages, or St. Augustine Horse & Carriage.
Snuggle up as you trot past cobblestone streets and gas lamps that glow just right around downtown St Augustine.
These rides aren’t just for tourists, as they’re a dreamy throwback that lets you wander hand in hand through the past.
Bonus: Most drivers double as storytellers, so expect fun facts, folklore, and a few cheesy jokes in the mix.
Winery & Distillery Tours
Level up your next date with a Corks & Forks Culinary Tour or the ultra-sleek Wine & Dine Culinary Tour, both offering sips, bites, and strolls through St. Augustine’s historic charm.
If you’re in the mood for something more guided, try the City Walks Food & Wine Tasting Tour or The Perfect Pairing: Wine, Cocktail and Food Experience.
Prefer to cruise in comfort? The Mobile Wine Tasting and Food Pairing Tour has you covered with curated stops and no risk of getting lost.
Plus, make time for a tasting at San Sebastian Winery, one of the most iconic date night ideas St Augustine has on tap.
Ghost Tours
Ghost tours might not sound romantic at first, but they’re the perfect excuse to huddle close and share a few playful scares.
Exploring haunted streets under moonlight adds just the right dose of thrill to your evening stroll.
Choose between a classic walking tour or a haunted trolley ride like the St. Augustine Ghosts & Gravestones Trolley of the Doomed, or go even deeper into lore with A Ghostly Experience, St. Augustine Creepy Crawl, or the Paranormal Investigation of Old Fort Grounds Tour.
They are eerie, exciting, and just mysterious enough to make sparks fly, especially when something goes bump in the night!
Visit “Love Trees”
Find the city’s hidden romantic icons by hunting for love trees—two species growing together as one—scattered across historic St. Augustine.
A top spot to start? The lush campus of Ponce de Leon Hotel (Flagler College), where the trees are as entwined as your weekend plans.
Don’t skip Aviles Street, where charm and history collide on one of the oldest roads in the United States.
According to local lore (and plenty of happy couples), stealing a kiss under these trees is one of the most tried-and-true St Augustine date ideas.
Sunset Cruises
Set sail on a St. Augustine Sunset Cruise with Live Music and Drinks for golden hour views that feel tailor-made for romance.
Whether you’re sipping on something chilled or swaying to live music, it’s the kind of vibe that turns a good date into a core memory.
Or opt for something extra special, like the Sunset Tasting Cruise and a Private Sunset Sailing Charter Along the Bayfront if you’re in the mood for uninterrupted swooning.
With other options like Florida Water Tours and the St. Augustine Dolphin Watch & Historical Harbor Tour, the breathtaking views and views of the city don’t stop—even when the sun does.
Cozy Bites, Candlelight Vibes & Waterfront Wow-Moments
Fine Dining
Elevate your evening with a reservation at Collage Restaurant, where white tablecloths and global flavors set the mood for something unforgettable.
If you’re into steaks and seafood, Michael’s St. Augustine brings the upscale Southern flair without being too formal.
Prefer historic ambiance with your filet? Raintree Restaurant serves it all in a restored Victorian home that practically whispers romance.
These spots are among the top-tier date ideas St Augustine has to offer, and your taste buds will thank you.
Waterfront Dining
Watch the sun sink into the horizon with fresh seafood in hand at Cap’s on the Water, where the vibes are just as delicious as the menu.
If you’re craving that toes-in-the-sand feeling without sacrificing quality, The Reef delivers oceanfront views and cozy tables built for two.
Whether you’re sipping a cocktail or sharing dessert, the setting alone makes this a must-do. Add this to your dreamiest night out in St Augustine Florida, and it’ll feel like a vacation (no plane ticket required).
Casual Charm
If your perfect date includes crab cakes and courtyard string lights, Harry’s Seafood Bar & Grille will charm your socks off. The lively atmosphere and Cajun flavors keep things fun without being fussy.
The Floridian adds a farm-to-table twist with Southern comfort food and vintage vibes that are equal parts trendy and timeless.
These relaxed gems are perfect for slow dinners and good convo—aka ideal for Augustine for couples just looking to unwind.
Wandering, Breathtaking Views & Lazy Day Magic in the Nation’s Oldest City
Historic Strolls & Sightseeing
Start with St George Street, where cobblestone paths, local shops, and charming cafés make every step feel like a postcard.
For unbeatable photo ops and centuries-old stories, walk hand in hand past the Castillo de San Marcos, where cannons and coastlines collide.
Pssst…hop aboard the St. Augustine Hop-On Hop-Off Trolley Tour by Old Town Trolley Tours if your feet beg for a break and you’ll be exploring the city like pros.
Bonus tip: Weave through the Colonial Quarter or take the St. Augustine Historic District Walking History Tour for a deeper dive into local legends and landmark architecture.
Beach Walks & Nature
Trade busy streets for sandy toes with a stroll along Vilano Beach, where crashing waves and quieter vibes set the perfect slow pace.
If you’re up for something a bit more active, head to Anastasia State Park for trails, shelling, and kayaking adventures that don’t skimp on scenery.
Level up the nature experience with a Wildlife Adventure: Boat Cruise & Kayak Eco Tour, where dolphins, birds, and mangroves are the supporting cast to your romantic lead.
Or spend a splashy day at Marineland Dolphin Adventure, and make a real connection with marine life at Anastasia State Park.
Museums & Culture
Step into the opulent Lightner Museum, once a grand hotel, now filled with antiques, art, and everything elegant.
Then marvel at the architectural fusion inside the Villa Zorayda Museum, inspired by the Alhambra palace in Spain.
For couples who like a touch of weird with their wonder, check out Ripley’s Believe It or Not!, Potter’s Wax Museum, and the historic Old Jail Museum.
From St Augustine History Museum to the St. Augustine Pirate & Treasure Museum, these stops honor Henry Flagler, Ponce de Leon, and the legacy behind the St Augustine Lighthouse.
Spa Day
Escape into serenity with a couples massage at the elegant Ponte Vedra Inn & Club, just a short ride from downtown. It’s not just a spa—it’s a full-on retreat with ocean breezes and plush robes included.
Whether you book a body wrap, facial, or full-day treatment at one of the luxury spas in St. Augustine, it’s the ultimate reset button.
And yes, it’s worth bragging that you’re relaxing in one of the most romantic spa towns in the United States.
Is Your Romantic Getaway Plan Ready for a Glow-Up?
Couples deserve more than just a dinner date and a quick stroll, especially in a place as timeless as St. Augustine.
From ghost tours to golden hour sails, there’s a treasure trove of fun things to do in St. Augustine for couples that make every moment feel special.
Start planning your dream trip with ease by checking out vacation packages through Tripster, where you can book all your St. Augustine attractions and hotels in one place.
Whether you’re going big with carriage rides or keeping it chill with beachside sunsets, everything you need is just a click away.
Make your list, pack your bags, and don’t sleep on the most charming things to do in St. Augustine for couples!
Things to Do in St Augustine for Couples FAQs
When is the best time of year to visit St. Augustine for a couples trip?
Spring (March–May) and fall (September–November) offer the best weather with fewer crowds and lots of romantic outdoor activities. These seasons also provide ideal conditions for beach strolls, alfresco dining, and festivals.
Are there any romantic hotels or bed-and-breakfasts in downtown St. Augustine?
Yes, St. Augustine is known for its charming inns and historic bed-and-breakfasts, especially near Aviles Street and the bayfront. Many romantic hotels offer couple-friendly amenities like private porches, spa tubs, and complimentary wine hours.
What are some unique date night ideas in St. Augustine?
Try a ghost tour with paranormal equipment, sip wine on a rooftop during a live music cruise, or do a chocolate and wine pairing walk. These offbeat experiences make for memorable and interactive evenings together.
Are there any romantic things to do in St. Augustine on a budget?
Absolutely! Walk hand in hand through St. George Street, visit the “love trees,” explore the Castillo de San Marcos exterior, or catch a beach sunset—all free or low-cost options. Many museums also offer discounted entry or free days.
Is St. Augustine walkable for couples exploring without a car?
Yes, the historic downtown area is very pedestrian-friendly, with most major attractions, restaurants, and shops within walking distance. For anything further out, the Hop-On Hop-Off trolley is a convenient and fun option.
Can couples do any water activities in St. Augustine?
Definitely—sunset sails, dolphin tours, kayak eco-adventures, and even brunch or wine cruises are all great options. Many launch from Vilano Beach or the marina near the Bridge of Lions.
What’s a good indoor date idea if it rains during our trip?
Visit one of St. Augustine’s unique museums like the Lightner Museum, Ripley’s Believe It or Not!, or Villa Zorayda. You can also enjoy wine tastings or spa treatments at luxury resorts.
Are guided food and wine tours worth it for couples?
Yes, they’re a fun way to sample multiple restaurants and local dishes in one evening without the hassle of planning. Many include curated wine pairings and historical storytelling for a well-rounded experience.
Where can I book couples attractions and packages in advance?
Use trusted platforms like Tripster to explore, plan, and reserve St. Augustine attractions and hotels. You’ll find vacation packages through Tripster that help save money and time.
