How To Enjoy Valentine’s Day in St. Augustine, Florida

The atmospheric and lovely ancient city welcomes you. Soak in all the sights on a romantic getaway. The best-rated St. Augustine Beach condos offer the perfect place to settle in so you can happily enjoy all the romantic activities.

But not sure where to start? We cover the top tours, events, and things to do to maximize the romance along the water.

Valentine’s Events & Tours

The dreamy atmosphere is in full display when you join one of the city’s top tours.

There are quite a few to go over and we certainly can’t cover them all. However, we highly recommend a tour with the Tasting Tours. Carefully curated seasonally, The Tasting Tours offers various routes for a romantic journey through the city via its top-quality restaurants, bars, and dessert shops. You can tour on a horse and carriage or a walking tour, covering top food and wine pairings or desserts.

It is one of the most revered romantic adventures in St. Augustine. All romantic St. Augustine vacations are made better with it on the itinerary.

We also recommend a visit to one of the more luxurious restaurants in the city. There are three that take the cake. These are Collage in downtown, Llama Restaurant on the island, and The Reef beachside. Llama, in particular, is stunning, a sensational and atmospheric one-room restaurant with authentic Peruvian dishes. 

Reservations are required for all the above listed restaurants. Contact them directly for hours and capacity limits.


Ready to see the sights with your loved one? We highlighted some quick and attractive romantic activities for your weekend getaway.

  • Anastasia State Park: This massive state park encompasses nearly half of the island and has many things to do away from the crowds, like kayaking, hiking, and settling on the beach.
  • Pasta 101: A. Chef’s Cooking Studio offers seasonal classes for cooking genuine top-quality pasta. Book today or else the spots for Valentine’s Day will be gone!
  • Sail the Schooner: The Schooner Freedom is a spectacular sailing ship housed in St. Augustine for decades. You can book a sailing adventure for a small group or pair and ride up the inlet under the sunset.

There’s no shortage of romance in the ancient city.

Take a Stroll in Washington Oaks Gardens 

couple holding hands on walk

Washington Oaks is spectacular and we would be remiss if we didn’t specifically cover it for you. Coated in thick Spanish moss, this entrancing park is an ideal romantic spot. It has a rose garden, best visited in the spring, where the colors truly pop and glow. There is a small beach with little foot traffic. Guests will see a small pavilion to relax and a trail along an open garden.

Entrance to the park is $5 per vehicle. It is open daily from sunrise to sunset. 

Watch a show at A Classic Theatre

A Classic Theatre is the defining performance arts theatre in the city. Led by an esteemed team of theatre lovers, like Deborah Dickey and Anne Kraft, A Classic Theatre provides quality community-led shows provoking new ideas in the theatre world. You can see that passion and drive for high-quality theatre in the play line-up, including shows covering the history of the Panama Canal and the work of Gertrude Stein. It is a lot more focused on challenging shows, history, and smaller runs compared to musicals and other showcase productions.

Theatre is just an amazing way to bond with a loved one. Stay connected on the website or through social platforms to see what the team is prepping for the 2021-2022 season. A Classic Theatre is located at 102 M L King Ave.

Get a Couple’s Massage

St. Augustine beach rentals may offer some relaxation on your trip, but it is hard to compete with a couple’s massage. We highly recommend a visit at the Spa at Omni Amelia Island Plantation north of St. Augustine. For an in-city stop, we recommend Small Indulgences or Debbie’s Day Spa and Salon. Both have full, half, and stress relief focused massage therapy.

Take in the View From the Lighthouse

Climb to dizzying heights and hold each other in the serene quiet atop the St. Augustine lighthouse, where on any given evening, you stand in full view of the shimmering lights of the city and the glistening waves of the ocean. Close your eyes and listen to the music of the crashing waves and keeling seagulls as the salt-tinged breezes caress your faces.

Dine at Michael’s Tasting Room

The ambient atmosphere of this Spanish-style wine bar and tapas restaurant will set the mood for an evening of exploration and intrigue in the Ancient City. The authentic food and live Spanish music will make you both feel as though you’ve been transported back in time to the early days of St. Augustine’s Spanish settlers, while the modern menu and wine selection will bring you back to the present moment.

Share a Kiss Under the Love Tree

At the Mission Nombre de Dios, there are two trees entwined tightly around one another—a palm tree and an oak—which are said to bind couples who kiss under their branches together forever. Embrace each other in a fairytale moment that is sure to bring good luck and greater memories.

Plan Your Next Adventure

St. Augustine is one of the area’s premier romantic getaways. Upon admiring the lights, the waterfront, and the historic architecture, it is easy to see why.

Go for a Ride in a Horse-Drawn Carriage

Take a private tour through the beautiful, weathered streets of St. Augustine’s historic district, immersing yourselves in the old world charm of narrow cobblestone streets and a city with a storied past, all accompanied with a bottle of wine.

Have a Sunset Picnic on Vilano Beach

Drive out to Vilano Beach for a picnic with your special someone, set against the stunning backdrop of the Florida sunset. Here, the two of you can share a glass of wine on the beach and a picture-perfect view from Porpoise Point of the romantic old buildings in downtown St. Augustine.