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Unique Date Ideas in St. Augustine

Fantastic Ways to Spend a Date in Our Old City

Valentine’s Day is just around the corner, but that doesn’t mean you have to wait until then to go on a romantic date. There are lots of fun, unique ways to spend time with your significant other in St. Augustine! Here are a few of our favorites:

Nights of Lights (Ends January 31st)

The Nights of Lights festival returns to St. Augustine every year, bringing with it a dazzling display of holiday lights. With just over a week left of the event, this would be the perfect way to spend a date night! During the Nights of Lights, businesses and restaurants tend to stay open later, meaning you’ll have plenty of time to dine and shop while you enjoy the beautiful displays of holiday lights.

Trains, trolleys, and cruises also offer seasonal tours that take you through the most breathtaking areas. There are also tours where you can walk, take electric carts, and get a spectacular view of the city decorated in lights from the air.

Check out our Nights of Lights Tours blog for some inspiration!

Horseback Riding

If you’re looking for a unique, fun date idea, why not go horseback riding on the beach? Equestrian Adventures of Florida offers horseback tours on the beach as well as several trails throughout Central Florida’s preserves.

If you have a particularly special occasion, you can also create your own riding experience with one of their custom ride packages. Whether you take a romantic tour along the beach or on a trail, you’re sure to have a date to remember!

Feeling Hungry?

If you’re looking to wine and dine, head over to the Ice Plant! This factory-style restaurant and bar was originally built in 1927 and focuses on creating locally designed drinks and farm-to-table healthy meals. The waiters and bartenders here serve specially shaped ice to perfectly complement your drinks.

For the ultimate date night, visit Michael’s Tasting Room. Not only do they offer incredible dishes using local and seasonal ingredients, but they also have an award-winning wine selection. When you book a reservation at Michael’s, ask about their Date Night Experience, which comes with an amuse-bouche, sparkling wine for two, and a three-course dinner.

St. Augustine Love Trees

The St. Augustine Love Trees are the famous trees that have grown together and become entwined with one another over time. There are at least seven of these love trees throughout the city, mostly in the Downtown District. While exploring the city with your loved one, make sure you keep an eye out for these trees, and don’t forget to take a picture!

Romantic Tours

Experience the beauty of St. Augustine while aboard a romantic, old-fashioned horse-drawn carriage. The 45-minute carriage ride will take you through the stunning historic streets of St. Augustine while you enjoy a bottle of wine. You’ll even get a pair of souvenir wine glasses to remember your date by!

If you’re more interested in food, check out the Wine & Dine Rolling Tour. This three-hour tour is for people 21 years and older. Head out on chauffeured city tour while en route to visit five amazing venues. This tour includes all-inclusive food and wine/beer.

If you’re looking for a Sunday morning date, check out the Brunch & Bubbles Rolling Tour, a chauffeured city tour that takes you to five incredible brunch and lunch venues. Enjoy your morning with 3 hours of food, bubbles, and wine!

Painting with a Twist

Create some unique and colorful memories when you visit Painting with a Twist! Their painting classes are great for date nights, girls’ nights, bachelorette parties, and even family days. Some of their unique classes include painting your pet and trivia nights. You are even welcome to bring along your favorite beverage and some light snacks to enjoy during your painting session!

Escape Rooms

If you’re looking for a thrilling and unforgettable date, look no further than Escape U Escape Rooms! Delve into one of their three uniquely designed rooms and use your wits to find clues and race against the clock. Work as a team to beat the challenge in under an hour! Currently, their adventures include: Save the Fleet, St. Augustine’s Old Jail, and Castillo de Matanzas.

Stroll the Streets

There are plenty of fun things to do in Downtown St. Augustine. You can stroll down the streets and peruse the shops, or you can head into some of the museums, galleries, restaurants, and other historic buildings in the area. Either way, it’s easy to spend an entire day in St. Augustine!

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