Some of the most popular romantic things to do in St. Augustine include sunset walks by the bayfront, candlelit dinners at historic restaurants and holiday light tours during Nights of Lights. Ghost tours, boat cruises, and carriage rides also make great options. Many couples enjoy combining dinner with a show or walk along the waterfront to make the night extra special.
Romantic Things To Do in St. Augustine for Couples
St. Augustine is one of the most charming and romantic destinations in Florida. Its historic streets, scenic waterfront and warm coastal breezes create the perfect setting for couples looking to reconnect or celebrate something special. If you’re planning an anniversary trip, honeymoon weekend, or even just a relaxing evening for two, there are countless romantic things to do in St. Augustine that promise unforgettable moments.
Watch the Sunset at the Bayfront or Vilano Beach
Few moments are more romantic than watching the sun dip below the horizon together. St. Augustine’s Bayfront near the Bridge of Lions offers a picture-perfect view as the sky turns shades of pink and gold over the Matanzas River. Bring a blanket and find a quiet spot by the seawall or walk hand in hand along the waterfront promenade. For a more secluded experience, head to Vilano Beach. The beachside pier and walkways provide a breezy, peaceful place to watch the waves and sky change colors. Don’t forget to stop for ice cream or a glass of wine nearby before or after your sunset stroll. Many couples enjoy extending their evening with a quiet dinner nearby. Some even bring a picnic or toast with a chilled bottle of wine. Sunset-watching is one of the most peaceful romantic things to do in St. Augustine and adds a special touch to any evening itinerary.
Take Old Town Trolley’s Nights of Lights Tour
(Seasonal)
If you’re visiting between mid-November and late January, experiencing Old Town Trolley’s Nights of Lights Tour is a must. This beloved tradition transforms downtown into a glowing wonderland with millions of white lights draped over buildings, trees and historic landmarks. It’s a magical backdrop for a holiday-themed date night in St. Augustine, FL. Couples can stroll through Plaza de la Constitución, book a cozy horse-drawn carriage ride or hop aboard the Nights of Lights Tour for festive music and narration. Some opt for a scenic boat cruise with Fury St. Augustine to see the lights from the water.
With shops staying open later and musicians performing throughout the square, the atmosphere is lively and festive. Plan ahead to grab a cup of hot cocoa or seasonal dessert as you walk. Visitors often say it feels like stepping into a fairy tale. However you choose to explore, this is one of the most magical seasonal romantic things to do in St. Augustine.
Enjoy a Romantic Dinner at a Local Restaurant
No date night in St. Augustine, FL, is complete without a delicious meal in a beautiful setting. The city’s culinary scene offers plenty of options for romantic dining:
• Columbia Restaurant: Dine on Spanish-Cuban classics in a historic setting filled with hand-painted tiles and wrought-iron accents.
• Catch 27: Focused on fresh, locally caught seafood, Catch 27 offers a relaxed yet refined dining experience with creative flavors and a charming courtyard.
• Michael’s: Known for its award-winning steaks and wine list, Michael’s features elegant decor and a quiet ambiance perfect for couples.
• Casa Reina: This lively rooftop restaurant serves Latin fusion cuisine with stunning views of the bayfront.
Many restaurants offer patio or balcony seating, where candlelight and ocean breezes complete the experience. Be sure to make a reservation in advance, especially on weekends or during busy travel seasons. Some venues offer live acoustic music or romantic lighting features to enhance the ambiance. Choosing the right dinner spot shows thoughtfulness and creates space for meaningful conversation. Picking the right dinner spot is one of the most meaningful romantic things to do in St. Augustine, allowing couples to slow down and savor the moment together.
Romantic Trolley or Carriage Rides
A nighttime tour through historic St. Augustine is one of the most relaxing and memorable ways to spend time together. Old Town Trolley Tours® offers narrated rides that highlight the city’s rich history, perfect for couples who enjoy learning together. For something more intimate, a private horse-drawn carriage ride is a timeless way to explore the streets. These rides often come with cozy blankets during the cooler months and follow routes through the prettiest parts of the old town. It’s a peaceful and picturesque way to enjoy a date night in St. Augustine, FL, especially under the glow of street lamps and twinkling holiday lights. Some companies offer customized routes or even champagne packages for special occasions. You’ll feel transported to another era as you take in the slow rhythm of the evening.
Go on a Ghost Tour for Two
Add a little thrill to your evening with a spooky walk through the city’s haunted past. St. Augustine is known for its ghost stories, and many local tours highlight the legends behind its oldest buildings. Ghosts & Gravestones® offers a theatrical, trolley-based ghost tour, while several companies provide walking tours or haunted pub crawls. You’ll visit cemeteries, old jails and historic homes while hearing tales of mysterious happenings. These nighttime outings are ideal for adventurous couples who like a mix of history, mystery and a few good laughs. Tours often include expert guides in costume who bring the city’s haunted heritage to life. It’s one of the more unexpected and playful romantic things to do in St. Augustine, especially if you’re both fans of a good story.
Take a Scenic Boat Cruise or Sail
St. Augustine’s waterfront is even more beautiful from the deck of a boat. Couples can book a sunset cruise or private charter to sail along Matanzas Bay. You’ll enjoy views of the Castillo de San Marcos, the lighthouse and the city skyline glowing in the evening light. Fury St. Augustine offers both group sailboat experiences and private bookings for those looking for a more exclusive night on the water. These cruises often include refreshments and soft music, making it easy to relax and reconnect. Some even offer champagne and special packages for proposals or celebrations. Experienced captains often provide fun facts about the coastline and local landmarks. If you’re looking for relaxing romantic things to do in St. Augustine, this one is hard to top. Bring a light jacket, especially in the cooler months, and enjoy the fresh air as you sail into the evening.
Catch Live Music or a Show
If you love music, make it part of your date night in St. Augustine, FL. Local wine bars and restaurants often feature acoustic sets, jazz trios, or singer-songwriters that set the mood. Check out spots like Prohibition Kitchen or Cellar Upstairs for live performances in intimate venues. The Colonial Oak Music Park also hosts outdoor shows under the canopy of massive oak trees, offering a truly atmospheric setting. For a theater option, visit Limelight Theatre or The Waterworks, where you’ll find rotating productions of classic plays and original works. Sharing live music or a show is one of the most memorable romantic things to do in St. Augustine, especially for couples who bond over the arts. Check performance schedules online before your visit to plan ahead. Local events often change seasonally, so there’s always something new to discover.
Visit the St. Augustine Lighthouse at Night
For something truly unique, consider booking a Dark of the Moon Tour at the St. Augustine Lighthouse. These special nighttime tours combine history, scenic views and a touch of paranormal fun. Couples can climb the tower together and look out over the city lights, then explore the lighthouse grounds by lantern. It’s a little spooky, a little romantic and very memorable. Guides share stories of former keepers, shipwrecks and unexplained phenomena, all while encouraging a deeper look into the city’s coastal history. This is one of the more adventurous romantic things to do in St. Augustine and ideal for couples who like something different. The climb to the top may be a bit of a workout, but the view is absolutely worth it.
Take a Wine or Spirits Tasting Tour
Start your evening with a tasting experience that sets the tone for the night. San Sebastian Winery offers complimentary tastings and a rooftop bar with live music on weekends. For something stronger, the St. Augustine Distillery offers guided tastings of small-batch spirits in a beautifully restored historic building. Both spots are close to downtown and easy to pair with dinner or a walk. Adding a tasting stop to your date night in St. Augustine, FL, adds flavor and fun to your outing, especially if you enjoy discovering new things together. Many couples turn the experience into a fun way to learn about local craftsmanship. Tours often include behind-the-scenes views of how the beverages are made, giving the outing an educational twist too.
Tips for Planning the Perfect Date Night
• Go Midweek: Tuesday or Wednesday nights are often quieter and more relaxed than weekends.
• Make Reservations: Many restaurants and tours fill up quickly, especially during Nights of Lights or holiday weekends.
• Plan for Parking: Use the city’s parking garage or consider a ride-share to avoid stress.
• Check the Weather: December through February can be cool at night, so bring a jacket or blanket if you’ll be outdoors.
• Combine Activities: For a well-rounded experience, try pairing dinner with a show, or a wine tasting with a ghost tour.
• Dress Comfortably: Wear shoes that can handle streets, and bring a light sweater even in warmer months.
A little planning goes a long way when creating a smooth, enjoyable date night in St. Augustine, FL. With so many romantic things to do in St. Augustine, you can mix and match experiences that suit your style as a couple.
FAQs
Bayfront Park near the Bridge of Lions and Vilano Beach are two favorite spots. Both offer panoramic views, sea breezes and plenty of room to relax. You can also catch beautiful sunset views from a boat on Matanzas Bay or from the rooftop of Casa Reina. It’s one of the simplest yet most memorable romantic things to do in St. Augustine.
Yes! From rooftop dining at Casa Reina to historic ambiance at Columbia Restaurant, there are many places perfect for a date night in St. Augustine, FL. Look for patios, candlelight and bay views for added atmosphere. Michael’s and Preserved also offer fine dining experiences that feel personal and special.
Try a ghost tour, sunset cruise or wine tasting at San Sebastian Winery. You could also book a nighttime visit to the lighthouse or join a haunted pub crawl. Taking a romantic carriage ride or catching live jazz at a local wine bar are also standout romantic things to do in St. Augustine.
Absolutely. This seasonal event is one of the most romantic experiences in the city. Choose a trolley, carriage or boat tour, or simply walk the historic streets hand in hand. It’s a top highlight for any date night in St. Augustine, FL, during the holidays, and many restaurants stay open late to help you make a full evening of it.
St. George Street, Aviles Street and the bayfront near Plaza de la Constitución are beautiful in the evening. Their historic charm, quiet corners and soft lighting make them ideal for strolling together. These areas also give you easy access to dessert spots, wine bars and scenic views. Street performers and boutique shops can also make the walk more engaging.
Yes. Try Casa Reina, O.C. White’s or River & Fort for great food and lovely views of the Matanzas River. These spots are perfect for enjoying a relaxed date night in St. Augustine, FL, by the water, especially around sunset. A waterfront setting creates a naturally calming backdrop for any meal.
