25 Ways to Fall in Love with St. Augustine Florida

What makes the best romantic getaways? A historic old town to explore or a delicious food scene to devour? How about large doses of nature and bountiful romantic attractions? Maybe you’re looking for some adult beverages and exciting nightlife or just want to relax and enjoy world-class amenities. You’ll find all of these romantic things to do in St Augustine and more!

With this 25-point list, you can plan a complete romantic getaway to St Augustine, Florida, or just add a special date night into your vacation to America’s oldest city.

Explore the City

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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.

Ride the Old Town Trolley or Red Train Tour

Photo Credit: Floridas Historic Coast.

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. 

There are two primary differences between the Old Town Trolley and the Red Train Tour. Old Town is a hop-on, hop-off tour, while Red Train is a continuous circuit. This difference gives you more options to explore with Old Town and choices on where to board, but it makes a lap on Red Train take less time with fixed seating.

The other difference is where the tour starts. Old Town starts from the Old Jail complex, and Red Train starts from Ripley’s Believe it or Not. Both companies offer free parking while you are on the tour. You can also package tours with their associated partners, Ripley’s for Red Train the Old Jail complex for Old Town.

​​Take a Romantic Carriage Ride

Photo Credit: Floridas Historic Coast.

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. Except, perhaps if you include a bottle of wine and a pair of keepsake glasses like they offer at The Tasting Tour. You’ll want to book ahead for this special carriage tour and not just hope for the best.

If you really want to spice things up, you can add a charcuterie board to the experience for an additional fee. You can even add a third or fourth person to your romantic journey if you so desire. While your relationship might not allow it, they’ll certainly fit in the carriage. Any more than four, and you’re back to a train scenario.

Explore the St Augustine Historic District on Foot

Photo Credit: Jenn Coleman.

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. St George Street runs through the heart of the historic district, but it’s only open to foot traffic. That’s right; you have to be walking to enjoy this exquisite collection of boutique shops and specialty restaurants.

You can hire a guide or create your own self-guided walking tour of St Augustine. Either way, you’ll enjoy one of the most compact and pedestrian-friendly cities in America

Indulge In the St Augustine Food Scene

Photo Credit: Jenn Coleman.

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. They keep the chain restaurants at bay while making culinary magic with fresh-caught seafood, farm-to-table vegetables, and an almost European flair. When you visit St Augustine, be sure to eat local and keep this tradition going.

Munch a Brunch

Photo Credit: Ancient City Brunch Bar.

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?

St Augustine’s brunch choices are, well, historical with plenty of yummy options. However, we have our eyes and stomachs set on the Ancient City Brunch Bar when we come back. We had a taste of their sweet treats and lattes during our food tour and want to come back to experience their famous Bruncharcutrie Boards.

Take a Food Tour

Photo Credit: Jenn Coleman.

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. You can’t even hit them all with a single food tour, but more stops are better than one, plus you get to explore the district with a fun guide.

Our ‘most romantic food tour’ has to be St Augustine Experiences’ Not Just A Chocolate Tour. You get up to five chocolate and sweets tastings from local shops and a gift bag of treats to take home. The tour lasts about 90 minutes as you wander through the old brick streets of the Ancient City.

Visit the Whetstone Chocolate Factory

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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 and how it goes from tropical beans to the world’s favorite confectionery, including a tour of the production facility.

The term ‘factory’ is a bit misleading but in a good way. I can relate to the Whetstone story of an engineer who wanted to do something different with his life, so Henry and Ester Whetstone opened a small ice cream store on St. George Street. Their chocolate fantasies blossomed with an exclusive contract for Disney World that evolved into production contracts with every major chocolate supplier, including developing a critical step in creating Hershey Kisses.

Mass producing chocolates in a 10,000 sq. ft. facility seemed closer to engineering than a sweet shop on St George, so they downscaled the business to small-scale production on King Street. That’s where they operate today, where they produce chocolate with only the finest beans that ship fresh daily.

Have a Romantic Dinner at a Local Restaurant

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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.

Some of the ‘must try’ restaurants include The Floridian with upscale southern cuisine, the Ice Plant Bar with fresh farm-to-table food, and the freshly caught seafood at Catch 27. These were our dinner choices, but we can’t wait to come back and experience more of the St Augustine food scene.

Venture out into Nature

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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.

Go to the Beach

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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. It’s everything that love is and can be wrapped into a singular moment.

St. Augustine features 42-miles of beautiful beaches, from the upscale coast of Ponte Vedra Beach to the pristine shores of the GTM Preserve and south to Crescent Beach. The quiet beaches of St Augustine make the perfect counterpoint to the bustle of the Historic District.

Ride a Bike

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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.

Biking in St. Augustine features over 150-miles of dedicated bike trails and bike-friendly streets where you pedal on elevated boardwalks over alligator-filled wetland marshes and ride under a canopy of tropical trees. You’ll find some of America’s best rail trails, not to mention the gemstone of this entire biking belt, the Ancient City herself – St. Augustine. Feel the salt breezes as you bask in ocean views and estuary escapes on your perfect bike date.

Partake in a Paddle

Photo Credit: Floridas Historic Coast.

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. This network of brackish saltwater marshes and estuaries is a paddler’s dream. You can explore for hours around islands and inlets with nothing but birds to keep you company.

Explore the GTM Preserve

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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.

Start your visit by stopping by the welcome center, where you’ll learn why this ecosystem is so important for everything from protection from storm damage to commercial fishing. Then you’ll have options for your visit, from renting a paddle craft from the outpost to hit the water or renting a fat tire bike to pedal the trails. You could also choose to hike the trails through the estuary or cross over to the ocean side, where you’ll find the more pristine beaches in the area.

Tour Romantic Attractions

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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. However, many of these attractions make fabulous dates, and we’re only including the best of the best romantic things to do in St Augustine here.

Visit the Castillo de San Marcos

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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. Maybe it’s the views from the ramparts. Who knows, but the Castillo de San Marcos is one of America’s only ‘castles’, so it’s making the list.

The Castillo is unapologetically a fortress. Its cannons defended the harbor of St Augustine for centuries. It has been attacked several times and besieged twice. It has never been conquered, but it has changed hands six times through treaties. The building closes at 5:00, but the grounds remain open until midnight, so you can always take your after-dinner stroll to the Castillo to make room for dessert. This strategy is particularly useful if you’re going to a ghost tour that starts from the old town gate afterward.

Climb the St Augustine Lighthouse

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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. Maybe she was only pining for a solitary man, or perhaps she imagined his quads after carrying buckets of oil to the lamp every night. No judgment. You do, you boo.

The St Augustine Lighthouse has 219 spiraling steps climbing 160′ up into the air. From the top, you get an aerial view of St Augustine and an unobstructed view of the Atlantic Ocean. You also get a pretty good workout on the way up.

Go to a Museum

Photo Credit: Jenn Coleman.

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.

Florida Historic Coast lists 22 museums in St Augustine, and other people claim the entire city is a living, breathing museum. So if you’re going on a museum date, pick something that interests both of you. Also, use this time to find the rhythm of your partner. No two people naturally go through a museum at the same pace, but if you can follow each other’s lead, it can be a tremendously rewarding undertaking. I know that we have bonded immensely over our mutually compatible shared appreciation of museums.

Take a Harbor Cruise

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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. From wine tasting to dolphins to city views, you’re sure to find a St Augustine harbor cruise that floats your boat.

Visit A Love Tree

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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.

There are about seven love trees scattered around St Augustine. Part of the adventure is to find one (or all) of them for your canoodling challenge. Maybe you’ll create a lasting tradition or just simply go on an afternoon snipe hunt. Either way, if it ends with a kiss, can it be that bad?

Have a Spirited Adventure

Photo credit: Jenn Coleman.

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. Plus, since the Historic District is so walkable, you don’t have to worry about driving back to your hotel.

Try Wine Tasting at the San Sebastian Winery

Photo Credit: Floridas Historic Coast

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?

San Sebastian is one of Florida’s premium wineries and a pioneer in using Florida’s local Muscadine grapes to craft premium, sparkling, and dessert wines. They also use Vinifera grapes for more traditional Chardonnay, Pinot Grigio, Petite Sirah, and Cabernet Sauvignon along with Port and Cream Sherry dessert wines. In all, they have won over 700 awards for excellence in winemaking and counting.

Visit the St Augustine Distillery

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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. Augustine better for future generations. They preserved, restored, and transformed Florida’s oldest ice plant into America’s most visited craft distillery.

We liked all their liquors, but we loved their mixers. Made with Florida harvested ingredients like pure cane sugar, grapefruit, and cinchona bark (where you get quinine from), they offer a taste of the Sunshine State in every glass.

Go on a Brewpub Crawl

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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. From there, take a 20-minute walk to the granddaddy of St. Augustine craft beer, Dog Rose Brewing Company on Bridge Street in Lincolnville. 10-minutes farther, you reach Ancient City Brewing’s taproom just off the town square. Saunter across the square to sample A1 Ale Works‘ extensive collection of some of the best Florida craft beers. Finally, cross the Bridge of Lions to reach your final stop at Old Coast Ales.

If you want to make the full spirited circuit, stop in at San Sebastian Winery and St Augustine Distillery since you’ll be walking right by them.

Partake in St Augustine Nightlife

Photo Credit: Jenn Coleman.

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.

Take a Ghost Tour

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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 ghost tours take you through ancient cemeteries, a funeral home turned B&B, and the old city gates where ghosts are rumored to greet incoming guests. If you don’t think ghost tours make for a good date night, think again. Afterward, you will not want to sleep alone, if you sleep at all…sounds like a successful date night to me!

Listen to Live Local Music

Photo Credit: St. Augustine Ponte Vedra
The Beaches Visitors and Convention Bureau VCB.

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. For sure, we know that Jimmy opened for local legend Gamble Rogers there and later dedicated his Fruitcakes CD to Gamble after his death.

Visit St Augustine has an excellent resource page to find local live music. There you’ll find anything you’re looking for, from Blues to Bluegrass to Rock and R&B. Don’t be surprised if there are a dozen or so venues open and jamming on any given Saturday night.

Come to Festivals and Concerts

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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. The Amp offers more than 40 top-tier events every year.

St Augustine offers a full slate of festivals and events in addition to the performances at The Amp. Combining an activity that you love with the magic of St Augustine creates a perfect framework for an unforgettable vacation.

Experience the Nights of Lights

Photo Credit: Jenn Coleman.

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. The downtown businesses and many residences light up their buildings, creating what National Geographic describes as one of the world’s most dazzling holiday light displays.

From trams to prams, boats to floats, there are almost as many ways to see the lights as there are participating businesses. No matter how you choose to see the lights, be prepared for something special.

Relaxing with the Amenities

Photo Credit: Ponte Vedra Inn and Club.

One of the best ways to enjoy the romance of St Augustine is with the amenities at your host hotel. Here’s how.

Stay at a Romantic Inn

Photo Credit: Jenn Coleman.

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. They offer bikes to guests, or you can walk and explore the district and then return to your secluded retreat with gardens, a fire pit, and a pool. Best of all, it’s all child-free.

We also loved The Ponte Vedra Inn and Club 20 minutes up the coast. It’s a five-star / five-diamond property that offers a true luxury beach resort experience that generally emphasizes golf, tennis, and general wellness.

Take a Spa Day at Ponte Vedra

Photo Credit: Ponte Vedra Inn & Club.

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. You can eat a delicious meal at the Gourmet Spa Café while you’re relaxing at the outdoor specialty pool and therapy grottos.

A spa day is a perfect way to unwind and relax after a weekend of walking through the brick streets of historic St Augustine.

Romantic St Augustine FAQs

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Is St Augustine a romantic city? St Augustine’s idyllic oceanside setting and old world charm makes it one of the most romantic cities in America.

Can you walk around St Augustine with alcohol? The City of St. Augustine prohibits drinking alcoholic beverages in public.

Does St Augustine have a good nightlife?With plenty of bars and pubs, you can find live music almost every night as well as delicious food at the city’s many local restaurants.

Wrapping Up the Most Romantic Things to Do in St Augustine

Photo Credit: Jenn Coleman.

When Henry Flagler came to St Augustine in 1883, he fell in love with the history and scenery. He moved to the city and began the construction of Florida’s first true luxury hotel, the 540-room Ponce De Leon Hotel. As the years went on, the Ponce became Flagler College, but St Augustine remained one of the premier romantic destinations in Florida and all of the United States. Now the Ancient City is filled with romantic things to see and do.

Take a romantic getaway in St Augustine, Florida. You might find yourself coming back, again and again, to catch up on activities missed and to find new experiences to enjoy.

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