6 Ideas for a Romantic St. Augustine Getaway

Reconnect with these Romantic Couples’ Activities in St. Augustine, FL


St. Augustine is not just the oldest city in the country, it’s one of the most romantic cities as well: European style buildings with balconies and flowerboxes, horses clip-clopping along brick streets, and lights reflecting off the water. Throughout the city, love is around every corner–St. Augustine is so romantic, it even has several love trees!

We’ve put together a short list of some of the most romantic things to do in St. Augustine–perfect for the couple looking to reconnect while on vacation. Here are six of our favorite things:

romantic getaway in St. AugustinePrivate boat tour. There are lots of great things to do on the water in St. Augustine–a sunset sail on the Schooner Freedom, a rowdy bash on the pirate ship, SUP paddleboarding at the Vilano beach pier. But my favorite boating excursion is the private sail with Sailtime Northeast Florida. This boating company is located in Camachee Cove, which is at the base of the Usina Bridge on the way to Vilano Beach.

Sailtime will provide you with a captain, first mate, and a spectacular boat. I love their catamaran, because it has the huge hammock that is suspended over the water. Laying in that netting, the water furling in white splashes underneath me, the blue sky above me…I’m getting lost in a daydream just thinking about it!

Sailtime has an entire fleet of boats–let us know what sounds good to you, and we’ll see if they have one available. But book early–the private boat tour package is limited to one sail a day. Call us at 904.824.4301 and we’ll be happy to book a sail for you.

2. San Sebastian Winery and Whetstone’s Chocolate Factory Tour. We shouldn’t have to explain the romance quotient in wine and chocolate–so what a great idea to 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, the true chocolate lover 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.

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 7 wines so you can choose your favorites. If it’s a weekend, you can 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.

Tickets can be bought at the door for the Whetstone tour (fee required), and winery tours are free and given every 20 minutes until 5:00pm. San Sebastian Winery, 157 King Street, 904.826.1594. Whetstone’s Chocolate Factory, 139 King Street, 904.825.1710.

3. Couples massage. You don’t 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.

couples getaway in St. Augustine, Florida4. Dinner in a small dark 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 old, narrow 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), Michael’s Tasting Room (amazing food plus a dreamy, romantic atmosphere and interesting wine list), and Old City House (we’re a sucker for the old stone buildings).

We also get all googly-eyed over the ambiance at Cap’s on the Water. Located on Vilano Beach (about a 10-15 minute drive from the inn, depending on traffic), 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.

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 and umbrellas!

6. See your favorite band. 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 Amphitheatre! They have a huge variety of acts all year long, from Vince Gill to Alice in Chains to Widespread Panic to Wu Tang Clan…seriously, if you like music of any kind, you’ll find an act that’s right up your alley. The Amphitheatre is just across the Bridge of Lions, literally a few minutes from our inn. See their schedule at www.staugamphitheatre.com.


If you would like a romantic stay at our St. Augustine bed and breakfast, book your room now to ensure you get a reservation! Our calendar seems to fill up more and more quickly these days. Also, if you’re coming to town to celebrate a special occasion, check out our list of St. Augustine’s best special occasion restaurants.