The 25 Most Romantic Things To Do in St Augustine Florida
Explore the City
St Augustine is famously known as the Ancient City and is America’s oldest city, so it makes sense to start your romantic Florida getaway by exploring the city. There are different ways to tour St Augustine, but you’ll only go wrong if you don’t venture out and explore.
Both the Old Town Trolley and Red Train Tour operate in St Augustine. Each tour follows a similar route and introduces you to over 100 historic points of interest along the way. Either one is a fantastic experience and an ideal introduction to St Augustine.
Some people enjoy trains; others find romance blossoms one-on-one with their partner. Nothing is more romantic for these traditionalists than an old-fashioned horse-drawn carriage.
Explore the St Augustine Historic District on Foot
The St Augustine Historic District resides roughly within the boundaries of the old city walls. Only the old gate remains, but you still see how the town spreads out from the central plaza.
We loved the St Augustine food scene because the locals love it. More than just eating where the locals eat, the dedicated community of local purveyors creates a one-of-a-kind experience.
A modern troubadour once sang – Girls Just Want to Have Brunch. This might seem a little weird, but brunch is the most romantic meal of the day. Is there a better way to celebrate sleeping in and snuggling?
On the subject of food tours, you should take one. Heck, you should take two because a bunch of brunches isn’t the only overwhelming food choice in St Augustine. There are way too many yummy treats to taste on a single visit.
If you’re looking for a just chocolate tour, go straight to the factory, St Augustine’s own Whetstone Chocolate Factory, that is. On the Chocolate Tasting Tour, you’ll learn everything you ever wanted to know about the history of chocolate
The classic date is dinner and a movie. However, the local restaurant scene is so good in St Augustine that we suggest you skip the movie and order dessert. Then, walk through the Historic District to work off the calories.
The Spanish settled St Augustine to drive the French out of Fort Caroline, near modern-day Jacksonville. They dispatched the French quickly in a series of massacres at the Matanzas Inlet. The Spanish kept their colony at St Augustine, but Jacksonville’s location at the mouth of the St. Johns River proved to be a more suitable location for industrialization. The city of Jacksonville flourished while St Augustine remained rich in history and natural beauty.
There’s a reason that enjoying long walks on the beach at sunset (or sunrise) is a dating cliché. The world is quiet, except for waves crashing on the sand and the song of sea birds and infinity is visible watching the Earth curve at the horizon.
At Coleman Concierge, we believe that couples that bike together stay together. The important caveat to that statement is that it applies to couples who successfully bike together. Some couples like to ride tandem, while others prefer to crank out miles. When you find your cadence, nothing beats biking as a way to bond and explore at the same time.
Some people’s language of love is paddling, and by that, we mean taking a SUP, kayak, or canoe out onto the water. The Matanzas and Tolomato Rivers converge at the St Augustine Inlet and flow into the Atlantic Ocean.
The Guana Tolomato Matanzas National Estuarine Research Reserve is a mouthful; that’s why locals just call it GTM. It’s located a few miles north of town at the confluence of the Guana and Tolomato Rivers and it’s the perfect place to get outdoors in St Augustine.
The internet lists over 90 fun things to do in St Augustine, but I wouldn’t call all of them romantic. For example, it takes a lot of kink to think that the Medieval Torture Museum constitutes a date night...lol!
There’s something intrinsically romantic about visiting a castle. It’s enough to make you forget that they were military forts, often with prisoners held captive in the dungeons. Maybe it’s dreaming of a fairytale romance, knights, and princesses.
Lighthouse keepers hold a special place in romantic lore. In the Summer of Love, Erika Eigen sang about wanting to marry a lighthouse keeper and keep him company.
Neurotypical people claim museums are the perfect alternative to dinner dates because you spend time together in an environment where you can talk and have something to talk about. People on the other end of the spectrum can appreciate not having to talk or even make eye contact. Life is about choices, and so is the museum scene in St Augustine.
If you don’t think that wind, water, wine, and sunsets are romantic, you need to take a 100-hour Hallmark movie crash course on romance. Once you get your compass calibrated, come on down to the docks for some nautical fun.
St Augustine’s Love Trees occur when two separate tree species grow in, on, and through one another. The local tradition is that if you kiss beneath a Love Tree, you’ll share an everlasting romance.
For centuries, young lovers have turned to the spirit world for amorous advice. That is to say, the world’s most popular love elixir, alcohol. St Augustine’s spirit scene is spooky good.
We’ve already talked about getting a bottle of wine for your carriage ride or harbor tour. Did you know that St Augustine is also home to the San Sebastian Winery?
The St. Augustine Distillery is a perfect example of this town’s community spirit. In 2013, the historic ice house seemed destined for development. Instead, a collection of 20 local families came together with a common vision: creating world-class spirits and leaving St.
Why just go to one brewpub when you can complete a 2.2-mile Brewpub Crawl in under an hour? The circuit is simple. Start at Bog Brewing on King Street, just across the San Sebastian River from the historic district.
Just because St Augustine is America’s oldest city doesn’t mean that the fun stops when the sun goes down. If anything, it has been around long enough to realize that age and time are just numbers. Don’t expect some rah rah rager; the Ancient City is far more sophisticated than that.
On the subject of spirits, many people believe that St Augustine is one of the ten most haunted cities in America. Who would have thought that a city founded on the massacre of 300 Frenchmen with one of the New World’s largest forts would be haunted?
St Augustine has a long and storied tradition of local music. Rumor has it that Jimmy Buffet got his start at Tradewinds Lounge, where they told him that he would never make it in the music industry.
The St Augustine Amphitheater is the largest venue in North Florida, with almost 5,000 seats. The natural beauty of Anastasia Island State Park enhances the outdoor seating to provide a beautiful setting for an incredible concert experience.
Of all the festivals in St Augustine, nothing is more romantic than the Nights of Lights. This festival traces its origins back to the Spanish practice of displaying a white candle in windows during the Christmas holidays, symbolically making room in their homes and hearts for Jesus.
St Augustine has some of the most romantic hotels in Florida, but here are two properties that we absolutely loved. The Collector Inn has 30 rooms located in a series of historic cottages just a couple of blocks away from the Historic District.
Ponte Vedra is an exclusive property for guests and members only. However, there is a loophole. Book a robed service, such as a massage for two in a private couples suite, then spend the rest of the day enjoying the spa facility.