6 Ideas for a Romantic St. Augustine Getaway

Nestled in the heart of Florida, St. Augustine isn’t just the oldest city in the U.S.; it’s a romantic haven where history and charm intertwine. Picture European-style buildings adorned with colorful flowerboxes, the rhythmic clip-clop of horses along brick-laden streets, and the enchanting glow of lights dancing off the water. In St. Augustine, love isn’t just in the air; it’s etched into every corner of the city, including its famed love trees! For a fun photo opportunity, visit the nearest one on Bridge Street by the elementary school. Ready to immerse yourself in this amorous ambiance? We’ve curated a list of the most romantic experiences in St. Augustine, perfect for couples seeking to rekindle their spark on vacation. Here are six of our top picks:

Romantic couple holding hands on a sailboat near St. Augustine, FL

1. Private Boat Tour

Among the myriad aquatic adventures in St. Augustine, our top pick is the exclusive sailing experience offered by Sailtime Northeast Florida. Based in Camachee Cove near the Usina Bridge on the way to Vilano Beach, Sailtime presents a bespoke sailing journey complete with a captain and first mate. Their catamaran, boasting a sprawling hammock suspended over the water, offers an unrivaled sense of serenity under the blue skies. With a diverse fleet at their disposal, Sailtime ensures a memorable sail, but remember to book early as the private tour is limited to one per day. Call us at 904.824.4301 and we will help you book your adventure. Looking for more options? Try a sunset sail on the Schooner Freedom, a rowdy bash on the pirate ship, or SUP paddleboarding at the Vilano beach pier.

Pro Tip: For an extra touch of luxury, opt for Sailtime’s sail featuring a private chef, elevating your romantic escapade to new heights.

Couple enjoying red wine and charcuterie during a romantic getaway in St. Augustine

2. San Sebastian Winery & Whetstone’s Chocolate Factory Tour

We shouldn’t have to explain the romance quotient in wine and chocolate–you can combine the two in St. Augustine! Start at Whetstone’s Chocolate and get a tour of the factory where they make their most popular chocolates. The tour is fun (you have to wear hairnets–so you’ll start things off with a laugh!), and the chocolate is delicious. Plus, true chocolate lovers will appreciate the history of chocolate making, as well as the tastings focusing on the subtle differences between various chocolates. After the tour you can get an iced hot chocolate (our favorite), and a box of candy to take home in their gift shop. Tickets can be bought at the door, fee required. Call them with questions at 904.825.1710.

Just a few doors away from Whetstone’s is the San Sebastian Winery. You’ll learn more about the grapes grown for these award-winning Florida wines, then have an opportunity to taste seven wines so you can choose your favorites. If it’s a weekend, head upstairs to their Jazz & Blues Bar, and enjoy more drinks, as well as an amazing overhead view of the west end of the historic district. Tours are free and given every 20 minutes until 5:00pm. Call the winery with questions at 904.826.1594.

Pro Tip: If you like tours with alcohol, also plan on taking the free tour at the St. Augustine Distillery. Their gift shop has lots of super cute souvenirs to remember your romantic visit by!

Romantic St. Augustine couples massage

3. Private Couple’s Massage

Treat yourselves to ultimate relaxation after your other romantic adventures around St. Augustine. You don’t even have to be on a reality dating show to enjoy a relaxing massage for two–you can arrange to have this little luxury right in your room! We’ll schedule two massage therapists to give you and your boo a Swedish, deep tissue, or sports massage–massaging your muscles while your stress melts away. Advance notice required; please inquire as to availability when booking your getaway.

Couple enjoying a romantic dinner and champagne at a restaurant in St. Augustine, Florida

4. Dinner at An Atmospheric Restaurant

After a relaxing massage, take a luxurious bath in one of our large jetted tubs, then put on your fanciest, sexiest clothes for an intimate dinner. St. Augustine’s narrow streets are lined with charming buildings–and some of our favorite restaurants are in those old buildings. A romantic restaurant is the perfect spot for reconnecting as a couple. Some of our favorites include Collage (we love the front room with the fireplace) and Sainte George Restaurant (great views of the fort and the bay). If you’re staying at our Beachcomber Cottages, check out the seafood at Pesca at the new Hyatt Place on Vilano Beach. In addition to Pesca, there is a romantic rooftop deck with drinks and small bites. Both restaurants are by Michael Lugo, the talented chef behind Michael’s downtown. We also get all googly-eyed over the ambiance at Cap’s on the Water. Also located on Vilano, Cap’s is old Florida at its most romantic–trees dripping with Spanish moss, white lights strung through the limbs, and right on the water. The food is delicious–you’ll find the list of fresh catches on a blackboard at the front entrance. If you’re coming to town to celebrate a special occasion, check out our list of St. Augustine’s best special occasion restaurants.

Pro Tip: The rooftop deck at Hyatt Place gets crowded for sunsets, so go early to snag one of the comfy outdoor couches.

Couple on the beach during a romantic getaway in St. Augustine, FL

5. Walk on the Beach

There’s a reason so many commercials show couples walking hand and hand through the sand. The sound of the waves, kicking water at each other–it makes you feel playful and fun! Drive about 15 miles south on A1A, and you’ll find Crescent Beach–a quiet, wide beach that has maintained its natural scenic charm. It’s one of our favorites for taking peaceful long walks. Our other favorite is Vilano Beach, in front of our Beachcomber Cottages. Vilano Beach has more shells than most beaches in St. Augustine, and it’s a favorite among shark tooth hunters. If you want to sit on any of the 20 miles of beachfront in St. Augustine, just ask to borrow our beach chairs.

Romantic St. Augustine bed with flowers, champagne and chocolate strawberries

6. See Your Favorite Band & Dance the Night Away

Do you remember the songs that were playing when you first started dating? Reignite that spark when you see those bands live at the St. Augustine Amphitheater! They have a huge variety of acts all year long, from Widespread Panic to Foreigner to the Beach Boys. No matter your taste in music, you’ll find an act that’s right up your alley. The Amphitheater is just across the Bridge of Lions, literally a few minutes from our inn. View the schedule to make your plans.

If you would like a romantic getaway at our St. Augustine bed and breakfast, book your room now! Our calendar seems to fill up more and more quickly these days.

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