St. Augustine, America’s oldest continuously inhabited European settlement, brims with enchanting activities for couples. This historic coastal treasure creates a romantic atmosphere with its cobblestone streets and timeless architecture that dates back centuries.
Romance seekers will find their perfect getaway here. The majestic Castillo de San Marcos, a masonry fort from 1672, stands as a testament to time. Couples can discover hidden treasures like the intimate Magic Hideaway speakeasy show at the historic Casa Monica Resort & Spa. The city’s charm extends beyond its prominent attractions. Lovers can seal their commitment with a lock at the secluded Vilano Beach or share a sunset view after climbing 219 steps at St. Augustine’s Lighthouse. The Lightner Museum, set in the former Hotel Alcazar from 1888, showcases fascinating exhibits. History buffs will love the locally owned St. Augustine Distillery, housed in a restored ice plant from 1917. The Old Town Trolley Tour takes visitors past more than 100 different points of interest. Couples can also paddle through the sparkling waters of Anastasia State Park. Each corner of St. Augustine holds a chance to create lasting memories together.
Start Your Romantic Getaway in the Historic District
St. Augustine blends centuries of history with modern comfort to create the perfect romantic escape. The Historic District makes a great home base that puts charm and convenience at your fingertips.
Check into a charming B&B or romantic hotel
St. Augustine’s historic bed and breakfasts give couples a chance at an intimate stay. The St. Francis Inn dates back to 1791 and combines old-world charm with modern comforts. A peaceful walled courtyard garden sits at its heart. History buffs will love Casa de Solana, the seventh oldest house in St. Augustine. This 250-year-old building started as a shelter for Native Americans and injured soldiers. Now it welcomes couples to its 10 unique rooms.
Many places offer romance packages to make your stay special. The Bayfront Marin House has some great options:
- Spa packages with champagne and chocolate-covered strawberries
- Anniversary celebrations with miniature wedding cakes
- Proposal packages if you’re ready to pop the question
The Casa Monica Resort gives couples a luxury experience that will make them “feel pampered and cherished”. These historic spots put you within walking distance of St. Augustine’s best attractions, so you can start exploring right away.
Evening stroll through St. George Street
St. George Street comes alive as the sun sets. This car-free street runs along an old colonial road from the 1700s. Many buildings here are either original or carefully rebuilt on historic foundations.
Couples can walk hand-in-hand past shops selling handmade leather goods, local art, and unique gifts. The street’s hidden courtyards give you quiet spots to pause and enjoy each other’s company. The colonial buildings make a perfect backdrop for photos, especially once the evening lights come on.
The magic really happens after dark. Lanterns light up the cobblestone paths, adding mystery to the street’s rich history. Couples can find cozy spots on second-floor balconies to watch people stroll below. Just look up now and then to catch all the beautiful architecture.
Dinner with a view at St. Augustine Fish Camp
St. Augustine Fish Camp takes waterfront dining to another level. The restaurant sits right on the water, setting up perfect views for a romantic dinner.
The patio becomes extra special at sunset. You’ll hear gentle waves nearby while you browse their drink menu. This spot captures everything great about dining on Florida’s coast. People love the clean, modern feel both inside and out.
Fresh seafood stars on the menu here. The key lime pie and crab cakes get lots of praise. You might wait a bit without reservations, but great service and water views make it worth it.
The restaurant stays open until 9pm Sunday through Thursday and until 10pm on Fridays and Saturdays. This timing lets you watch day turn to night over the water—a perfect start to your St. Augustine adventure.
Explore Hidden Historical Gems Together
St. Augustine’s charm extends beyond its busy tourist attractions. The city holds historical treasures where couples can share intimate moments surrounded by centuries-old stories. These hidden spots create the perfect setting to make lasting memories.
Visit the Lightner Museum’s secret gardens
The Lightner Museum sits in the historic Hotel Alcazar, built in 1888, and has more to show than its impressive Gilded Age artifacts. The south terrace and garden have gotten a refresh and stand as a true romantic hidden gem. This peaceful space has changed the museum’s feel by adding a vibrant community garden and outdoor area that stays true to Henry Flagler’s original vision.
The stunning Fountain Plaza anchors these gardens with original fountains designed by Flagler’s architects, Carrère and Hastings. Couples stroll hand-in-hand along brick-tiled paths until they reach the Oak Shade Garden. Here, an ancient oak draped with Spanish moss creates a natural canopy – just right for quiet conversations.
The interior courtyard’s serene koi pond and charming footbridge give couples a chance to feed colorful fish and take memorable photos. After seeing the museum’s three floors of elegant furniture and fascinating artifacts, Café Alcazar awaits. This unique spot sits where the hotel’s deep-end swimming pool once made a splash.
Find the Pirate & Treasure Museum
The St. Augustine Pirate & Treasure Museum at 12 South Castillo Drive gives couples an unusual yet engaging look at maritime history. This unique attraction takes visitors back 300 years to Port Royal, Jamaica, during the Golden Age of Piracy.
The museum showcases an impressive collection of pirate artifacts including:
- One of the only remaining authentic Jolly Roger flags
- Real treasure chests to touch and explore
- Props and costumes from famous pirate movies
The exhibits go beyond simple displays with audio shows, cannon demonstrations, and knot-tying activities. Adults pay $19.00 to join this swashbuckling adventure from 10 am to 7 pm daily (closed on Christmas Day).
Take a quiet walk around the City Gate and Castillo walls
The historic City Gate sets a romantic mood for couples who want a peaceful walk away from the crowds. Built in 1808 entirely from coquina, these pillars mean more than just marking St. George Street’s entrance.
The gate was part of the Cubo Line, a defense system that stretched about half a mile from the Castillo de San Marcos to the San Sebastian River. This first line of defense combined an earth wall covered with sharp-leaved yucca and a nine-foot palm log stockade.
Modern streets now cover the defensive walls, but couples can walk through the same gate that kept residents safe over two centuries ago. This spot sits right across from the Castillo de San Marcos and gives couples a quieter option than the busy attractions. It’s ideal for those who want both history and romance.
These historical gems let couples see St. Augustine’s rich past while making their own special memories together.
Unwind in Nature and Secluded Spots
St. Augustine’s natural beauty sets a romantic mood with quiet spots where couples can escape the tourist crowds. These peaceful retreats let couples connect while surrounded by stunning coastal views.
Canoe or paddleboard at Anastasia State Park
Anastasia State Park sits just a mile from the downtown historic district. This natural paradise spans 1,600 acres of pristine landscape where couples can find both excitement and peace. The park’s rich ecosystem makes it perfect to paddleboard or canoe through Salt Run inlet’s calm waters.
Couples can rent kayaks, canoes, or paddleboards from Anastasia Watersports and explore as they wish. The calm waters welcome beginners, and no experience is needed to enjoy this popular activity. The real magic happens when couples spot wildlife together in waters filled with:
- Dolphins playing in the distance
- Manatees gliding beneath the surface
- Sea turtles navigating the waters
The paddling adventure gives amazing views of the St. Augustine Lighthouse. These views create perfect backdrops for couple photos. Couples can end their water adventure with a relaxing hour on the beach for a romantic and refreshing experience.
Watch the sunset at Freedom Park
Freedom Park stands out as one of St. Augustine’s hidden romantic spots. This quiet haven features a paved path with sweeping marsh views that create magical moments during golden hour.
The park’s whimsical love letter mailbox makes it special. Couples can read touching notes from past visitors or write their own love letter with the available pen and paper—creating a sweet memory of their time together. Benches scattered throughout the park give couples perfect spots to watch the sky turn brilliant shades of orange and pink.
Walk hand-in-hand on Vilano Beach
Vilano Beach remains a local secret that gives couples a peaceful escape from St. Augustine’s busier beaches. This beach north of the city charms visitors with quiet shores, soft sand, and stunning views of both the Atlantic Ocean and Intracoastal Waterway.
The pedestrian walkway over A1A in North Vilano Beach, known to locals as the “Love Bridge,” adds romance to any visit. Couples can mark their love by adding a lock—a sweet tradition that makes their romantic getaway more special. The pristine shoreline often feels private, perfect for intimate talks and finding seashells to remember their time together.
Add a Touch of Magic and Mystery
St. Augustine’s enchanting nightlife gives couples magical experiences that blend mystery with romance. The ancient city reveals its mystical side after sunset through exclusive performances, haunted adventures, and celestial celebrations.
Experience the Magic Hideaway show
The Magic Hideaway show is one of St. Augustine’s most luxurious hidden gems. You’ll find it inside the historic Casa Monica Resort & Spa. World-renowned magician Bill Abbott performs in a velvet-draped showroom that fits just 22 guests. The night starts with tableside close-up magic and leads into a one-hour show of mind-reading and sophisticated illusions.
A $125 ticket has a complimentary cocktail and a chance to take photos and get autographs with the performer. This Saturday night experience is TripAdvisor’s #1 Attraction and creates the perfect romantic date night in St. Augustine.
Join a haunted pub crawl or ghost trolley tour
St. Augustine ranks among America’s top 10 most haunted places, and its after-dark tours let couples cuddle closer. The original Haunted Pub Crawl, 20 years old, takes couples through three or four haunted bars while guides tell chilling tales of ghostly encounters.
The “Ghosts & Gravestones” tour on the Trolley of the Doomed will take you to:
- Tolomato Cemetery’s mysterious grounds, home to five-year-old James and the legendary Ghost Bride
- The old City Gates, where Elizabeth, a child victim of yellow fever, waves to visitors
- Potter’s Wax Museum’s Chamber of Horrors for a special nighttime experience
The trolley tour runs for 60 minutes, costs $36.39 per person, and stays in the PG-13 range—spooky yet good for most couples.
Climb the Lighthouse for a moonrise toast
St. Augustine Lighthouse’s monthly Sunset Moonrise tour is a chance to see nature’s perfect timing. The sun sets over the Intracoastal Waterway while the moon rises over the Atlantic Ocean.
San Sebastian Winery provides a champagne toast, and The Reef Restaurant serves delicious hors d’oeuvres. Couples climb 219 steps to reach 165 feet above sea level, where they enjoy 360-degree views that create an unforgettable romantic backdrop.
These special events happen once monthly and need reservations. Tickets cost between $30-35 per person. The mix of history, height, and heavenly views makes this one of St. Augustine’s most unique romantic experiences.
Savor Local Flavors and Unique Tastings
St. Augustine’s food and drink scene gives couples amazing opportunities to share sensory experiences and intimate tastings together.
Tour and taste at St. Augustine Distillery
A beautifully restored ice plant from 1927 houses the St. Augustine Distillery, which crafts world-class spirits using local ingredients. Twenty local families founded this distillery with a commitment to green practices. The distillery welcomes visitors with free self-guided tours and spirit tastings daily from 10:30 a.m. to 5:30 p.m. Guests can sample four signature cocktails that showcase their handcrafted vodka, gin, rum, and bourbon while discovering their “farm-to-bottle” approach.
Share sweets at Whetstone Chocolate Factory
The sweet spot for couples lies in St. Augustine’s “Original Chocolate Tour” at Whetstone Chocolate Factory. This 45-55 minute experience lets visitors taste four different chocolates and learn to spot subtle differences between dark, milk, and white varieties. Multiple tours run daily, with adult tickets at $10.95 and children’s tickets (ages 5-17) at $8.45. Adult visitors receive a $2.00 coupon they can use at the King Street store.
Enjoy rooftop dining at La Cocina or Cellar Upstairs
La Cocina at the Cellar Upstairs sits above San Sebastian Winery and offers breathtaking views of the San Sebastian River and marshes. Live jazz fills the air Tuesday through Sunday. Chef Norberto Jaramillo brings his Colombian roots and 20 years of expertise to create Latin American-infused world cuisine. The restaurant’s menu options range from bar bites to lunch, dinner, and special chef’s pairings.
Summing all up
St. Augustine has a wealth of romantic experiences that go way beyond its historic charm. The Historic District’s cobblestone streets and the majestic Castillo de San Marcos are just the beginning. Couples can find hidden gems throughout this ancient coastal city. Those who venture off the beaten path get rewarded with intimate moments at Freedom Park’s love letter mailbox. They can share a champagne toast at the St. Augustine Lighthouse while watching both sunset and moonrise.
The natural beauty comes alive as couples paddle through Anastasia State Park’s peaceful waters. Vilano Beach’s secluded stretches of sand create perfect spots for private conversations. The city takes on a different character at night. Magical experiences like the exclusive Magic Hideaway show and spine-tingling ghost tours give partners plenty of reasons to stay close.
Food lovers will definitely enjoy their culinary experience. From waterfront dining at St. Augustine Fish Camp to rooftop views at La Cocina, the options are endless. These spots go together with one another perfectly with tastings at St. Augustine Distillery and Whetstone Chocolate Factory. Each flavor becomes a shared memory and each sip celebrates time spent together.
This coastal city offers something rare in today’s world – a chance to step back in time while creating new memories. Couples looking for both adventure and intimacy will love this place. They can climb 219 lighthouse steps together, lock their love on Vilano’s “Love Bridge,” or simply stroll hand-in-hand through secret gardens. America’s oldest city remains one of its most romantic destinations. It promises couples not just a getaway but a genuine experience filled with shared discovery and enchantment.