Gay Florida Road Trip Guide: St. Augustine

St. Augustine Road Trip

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As luck would have it, my Big Gay Florida Road Trip overlapped my 40th birthday celebration. Since parties are out this year and social distancing in, I planned out my month-long journey with the intention of being in St. Augustine on my special day. Who wouldn’t want to toast to 40 years with a cup of water from the Fountain of Youth? My wife and dog even joined me for the celebration!

Margaret (left), Rachel (right) and Lola (the cute one in the front)

Founded in 1565, St. Augustine is on Florida’s “First Coast” and lays claim to being the oldest city in the U.S. Forty-two years before the English colonized Jamestown and fifty-five years before the Pilgrims landed at Plymouth Rock, the Spanish established at St. Augustine this nation’s first enduring settlement. The city features centuries-old Spanish-influenced architecture and iconic cultural sites.

There are an endless number of reasons to put a gay St. Augustine road trip on your travel bucket list. Nowhere else in Florida, let alone the U.S., will you find such picturesque architecture. And if winter is your favorite time to travel, then you’re in luck! St. Augustine lights up for Christmas. While the holiday season is the most breathtaking time to visit this European-influenced town, a St. Augustine road trip is perfect any time of year.

I spent four nights and nearly five days in St. Augustine. Even with the extended visit, there still wasn’t enough time to do everything on my list. Whether its museums to explore, souvenirs to purchase, beaches to enjoy, or food to eat, you’ll find it all in this charming town.

For more regional travel tips, check out our Northeast Florida Region guide.

How Gay is St. Augustine?

St. Augustine isn’t a gay town, but the LGBTQ community can be found all over the region, especially in this old city. In fact, ManAboutWorld named St. Augustine as one of the best ‘Gay places to go in 2015’. There’s even a gay-owned B&B or two (keep reading). So no worries – you’ll fit right in.

St. Augustine attracts people from all walks of life. While the politics lean more conservative, St. Augustine is welcoming to everyone.

Where to Stay

St. Augustine is known for Bed & Breakfast accommodations. Most are within walking distance of St. George St, the popular pedestrian-only thoroughfare lined with restaurants, shops, and attractions. However, the downtown area can get a bit crowded, so if peace and quiet is what you’re craving then it might be better to stay at one of the local hotels on the outskirts of town. Most hotels offer trolley and shuttle options into town.

Tryp by Wyndham

333 South Ponce De Leon Boulevard

Find comfort and easy access to the heart of St. Augustine at this ultra-modern property. Choose from traditional rooms and suites, some with balconies overlooking the San Sebastian River.

Unwind from your busy day of exploring with a wine or beer in the lounge, a dip in the pool, or soak in the hot tub. Guests get free parking and wifi, and there is a shuttle to get you to local attractions. Everyone will feel welcome here, including your four-legged family members.

The Tryp by Wyndham pool was cool, relaxing and perfect for an end-of-day dip. Photo by Rachel Covello

My Experience: I loved this property! The rooms were clean and spacious, bed comfortable, pool cool and relaxing, and property very attractive. But the staff is the main reason I would return to the Tryp by Wyndham over and over again. The General Manager went out of her way to make me feel special on my birthday by decorating the outside of my room.

To adhere to COVID guidelines, the lounge was closed during my stay, but I had no problem grabbing a couple of drinks to take to the pool or my room as needed. The breakfast staff also accommodated a few menu adjustments to meet my dietary needs and delivered meals directly to the room for isolation purposes.

The hotel was very quiet, which meant a good night’s sleep, but within close proximity to town and local restaurants.

Start planning your trip to TRYP here

At Journey’s End Bed & Breakfast

89 Cedar Street

Make yourself at home in the heart of Old Town St. Augustine. At Journey’s End is a relaxing oasis in the midst of all the action. The five rooms at this charming property have private baths and some features private outdoor areas.

Relaxation is taken seriously here. Enjoy complimentary cocktails and snacks in the afternoon then head to one of the porch rocking chairs to unwind and reflect on your day’s adventures.

This gay-owned property welcomes families including fur babies. Parking and breakfast are included. Start planning your journey here.

Other Places to Stay


Where to Eat & Drink

From casual to quality, the food and drink options in St. Augustine are endless. I filled my belly with seafood during my St. Augustine road trip and sampled a few other dishes and drinks along the way.

San Sebastian Winery

157 King Street

Wind down your busy day with wine at the San Sebastian Winery. Enjoy a complimentary tour and tastings of their signature wines. They’ve been producing and bottling on site since 1996. They are known for their award-winning dessert and sparkling varieties, but don’t miss the Vintner’s White – my favorite!

Head up to the Cellar Upstairs Wine and Jazz & Blues Bar to enjoy sips, snacks, and the sounds of talented local musicians. The only thing better than the wine and small plate menu offerings on this rooftop deck are the fantastic views of St. Augustine. Get all the details including tour and music schedules here.

My Tip: Order the charcuterie platter with your wine. Flavorful cheese and meats combined with generous portions make this a big win in my foodie book.

Charcuterie Platter at San Sebastian Winery. Photo by Rachel Covello


60 Hypolita Street

This intimate fine-dining spot has been romancing diners and their taste buds for over a decade. The beautiful artwork lining the walls of this cozy restaurant can’t compare to the creatively plated menu items. Collage’s eclectic global-inspired menu offers something for every palate including vegan options.

Favorites include fresh locally sourced seafood and produce, lobster ravioli, and rack of lamb. Their wine list is one of the most extensive in northeast Florida. Check out their menus, including daily specials, and reserve your memorable dinner experience here.

My Tip: You can’t go wrong with the Maple Leaf Farms Duck Breast. It was delicious. My wife had the Open Fire New World Paella, and while a beautiful presentation and popular with most patrons, as a seafood snob, it wasn’t her favorite version of a paella. But when I gave her my Homemade Butter Rum Cake, a birthday treat from the restaurant, it more than made up for her disappointment.

Open Fire New World Paella. Photo by Rachel Covello

Culinary Outfitters

173 Shipyard Way

Not everything is old in America’s oldest city. Head off the beaten path to one of St. Augustine’s newest restaurants that has fast become a local favorite. Culinary Outfitters has been serving-up delicious local seafood to locals for over 20 years. Now in a new bustling waterfront location with an 8,000 square feet patio and 250 seats there’s room for everyone.

Their innovative, fresh menu features fresh seafood, creative salads, and great burgers. Vegan, vegetarian, and gluten free diners will find delicious options too.

Culinary Outfitters also caters private and special events on site and off. Currently only offering take out check here for specials and reopening details.  

My Tips: This restaurant is a hidden gem and a local favorite. Everything on this menu is moan-worthy. The food was so good that I went twice. While you can order the standard entree, I enjoyed sampling a variety of appetizers for my main meal. I tasted several items, but the rich bisque Crab Soup with east coast blue crab and an old bay crouton was my favorite of them all. I also liked the Chili Charred Octopus, Charred Peel & Eat and the Fish Dip.

The Floridian

72 Spanish Street

For a new twist on the unique flavors of Old Florida head to the Floridian. Their creative and delightful menu offers innovative takes on classic southern cooking.

There’s something on their menu for everyone including vegans and folks avoiding gluten. Protein options include fresh seafood, tofu, and tempeh. Enjoy specialties like “Company’s Coming” (a southern-style charcuterie), blackened tofu and grits, or the “Southern Belle” entrée salad.”

The historic building houses a whimsical dining space and bar with beer, wine, and craft cocktails. Currently the Floridian is only open for carryout or dining on their outdoor covered patio and in their lush courtyard. See their menu and reopening updates here.

The Columbia

98 St. Goerge Street

Bask in the ambiance at this branch of the historic Tampa eatery. The Columbia St. Augustine provides a beautiful setting in the heart of Old Town. It makes for a great spot to relax with lunch, dinner, or even some sangria in their lush courtyard.

Enjoy specialties including favorites from the menu of Florida’s oldest restaurant (the Tampa Columbia opened in 1905)!  Try their famed Cuban Sandwich, chicken and rice, fresh seafood, and delicious small plate tapas.

The Columbia St. Augustine also makes a great setting for private events for up to 72 guests. Plan your visit to this oasis here.

My Tip: While I’ve had better seafood, the ambience is what makes this restaurant such a joy to visit. Don’t get me wrong – the food was delicious. But I didn’t venture here for the food. I was just excited to get swept away by the Spanish experience. I’m also addicted to fried plantains.

Harry’s Seafood, Bar and Grille

 46 Avenida Menendez

Find out yourself why Floridians are hooked on Harry’s. Harry’s has been serving-up southern and Creole-inspired dishes at their five restaurants around the state since 1987. Indulge in their take on southern favorites including fried green tomatoes and classic cocktails like Hurricanes and Bayou Bloody Marys. They also offer fresh seafood, burgers, and salads. A gluten-sensitive menu is available upon request.

My Tip – Try the crab-crusted Redfish Royale! Although not a local fish to Florida, the flavors of this plate were worth the Florida detour.

The St. Augustine location is housed in one of the city’s oldest bay front homes. Enjoy the charming dining rooms or the fun of live music in the lush courtyard overlooking the bay front scene. Well behaved leashed pups are also welcome in the outdoor dining area. Check out Harry’s menu and live music schedule here.


Like many Florida cities St. Augustine is home to a number of craft breweries. Many of the area’s taprooms are family friendly and have outdoor areas for optimum relaxation and refreshment. All offer beer to go, snacks and casual bites. Some offer full dining.

Just east of the old town on Anastasia Island is Old Coast Ales (300 Anastasia Boulevard). With up to 12 taps at a time there are plenty to choose from! They also offer wine, kombucha, and all natural sodas. Bring the family, including well-behaved fur babies, to lounge on their two patios or try your hand at the only ping pong table in town. Check out their beer menu and live music schedule here.  

Overlooking the bayfront on the edge of Old Town is A1A Ale Works and Taproom (1 King Street). They are known for their rotating selection of house crafted beers, their full bar, and diverse food menu. This large venue has indoor dining, two bar areas, and a small balcony overlooking the bayfront. They even offer catering and space for private events.  

Head west of Old Town to Bog Brewing (218 West King Street). This local microbrewery features seven rotating taps. The stand outs here are unique regional seasonal flavors such as smoked datil pepper ale. Enjoy sipping on site in the pet and family friendly open air beer garden.

What to Do on a Gay St. Augustine Road Trip

With all of the things to do in St. Augustine, my first recommendation would be to experience an Old Town Trolley tour on your first day in town. You can hop aboard to explore the region in its entirety or hop on and off at 22 different stops along the way. A one-day trolley pass is under $30 (if you order tickets online) and for only $10 more, you can get a two-day trolley pass. It’s worth every penny. Old Town Trolley also offers shuttle service from local hotels to the main station.

I used the Old Town Trolley map to navigate everywhere around town. These are some of the places I visited during my visit. Oh…and don’t forget to bring your camera! The photo ops are endless.

Ponce DeLeon’s Fountain of Youth Archaeological Park

11 Magnolia Avenue

Legend has it Ponce de Leon was searching for a magical Fountain of Youth. While there’s no evidence that he found it at this site it’s still a very cool place to explore. Archaeologists have been finding artifacts at this site for over a century.

Check out the sprawling waterfront property on your own, or with a knowledgeable guide. Aspiring Indiana Jones fans will “dig” the archaeological finds. And bird lovers wiIl appreciate the stunning peacocks wandering freely throughout the park. You can also bring your own furry friend. Pets are allowed on leashes.

Interact with interpretive historians throughout the park to learn the stories of the people who lived here for over the centuries. 

While here, head over to the Spring House for a sip from the alleged Fountain of Youth — it can’t hurt! I did, as I’m hoping to stay 40 forever.

Start planning your adventure here.

My Tip: Block at least two hours or more to enjoy everything this park has to offer. I loved the Discovery Globe presentation and the blacksmith exhibit. As mentioned in my Space Coast road trip article, I grew up near the Air & Space Museum in Washington, D.C. The planetarium at the Fountain of Youth paled in comparison to the one in DC, but it was still enjoyable and the perfect place to escape the heat.

Castillo De San Marco

1 South Castillo Drive

Just outside the walls of Old Town St. Augustine is the Castillo De San Marco. Built of Coquina Stone in 1672 the structure served as a military fortress and to protect the citizens of St. Augustine during invasions.

Now visitors can experience the grounds of the massive fort which make for some great photo opps. Check the park’s website for re-opening information and for their future tour schedule. The history and sweeping views of the Old Town and surrounding waterways are worth a visit. Get in touch with your inner pirate and plan your Castillo invasion here!

St Augustine Pirate & Treasure Museum

12 South Castillo Drive

Adventurers of all ages will enjoy this attraction that chronicles the adventures of generations of pirates. Explore the “Golden Age” of pirates through hundreds of authentic shipwreck arrrrrrrrrtifacts. See what I did there? Arrrrr? Pirates? Keep reading…

Learn about pirate life and marine archaeology from interactive exhibits. Take your turn firing a cannon and look for your own treasure on a special scavenger hunt throughout the museum.

When you’ve had enough entertainment, exit through the gift shop for a keepsake.

My Tip: Get in touch with your inner pirate or consider an immersive experience with a combo ticket that includes the Colonial Quarter. Personally, the pirate exhibit was one of my favorite stops in St. Augustine. It’s much bigger inside than it looks from the outside. That’s what he said!

Selfie moment outside the pirate exhibit.

Colonial Quarter

43 St. George Street

Go back 300 years for a glimpse into Spanish and British colonial life. Interact with knowledgeable guides who will lead you through life in historic St. Augustine.

Learn how St. Augustine’s diverse people adapted to living in the challenging New World. Painstaking restoration, research, and attention to detail make this a one-of-a kind historic site.

Check out demonstrations by artisans and crafts people using historic tools and techniques. Climb the 35-foot watchtower to keep an eye out for invaders! Enjoy lunch or beverages at one of three on-site eateries all just steps away from bustling St. George Street.

For all the details, including a schedule of live music on the Quarter’s stage, visit here.

My Tip: Make sure to join the tour. I only had time to walk through the property and I regret not making more time to enjoy the full experience. Fortunately, I ran into two fellow lesbians who shared the recap. See…gays are everywhere in St. Augustine. It truly was a gay St. Augustine experience!

Ronnie Havemann and Gail Bow on vacation from Titusville, Florida.

Saint George Street

At the Old City Gate to Cathedral Place

Stroll along St. George Street, one of the oldest streets in America for a leisurely glimpse into history. From the Old City Gate south to the historic Cathedral this pedestrian-only street will take you back in time to the eras of Spanish and British colonial rule.

Explore the quaint specialty shops that line the Old Town portion of St. George Street. Experience history and adventure in one of the several attractions. Enjoy a meal at one, or more, of dozens of eateries with something for every diner and every budget.

Insider Tip: Parking in and around the Colonial Quarter can be a challenge. There is a large pay-to-park structure located at the Visitor Information Center (10 West Castillo Drive). Plan your visit to this unique district here.

My Experience: I shopped till I dropped on Saint George Street. My wife, Margaret, bought me a stunning set of sterling silver fish earrings for my birthday. We also had antique photos taken at Heritage Old Time Portrait Studio.

Oldest Wooden School House Museum & Gardens

14 St. George Street

Go truly “old school” at the Oldest Wooden School House in the United States. Imagine what school days were like for the children of Minorcan settlers in this building from the 1700s.

Anyone who has spent time in a classroom will appreciate the preserved artifacts and displays of old school “reading, writing, and arithmetic” set up exactly as they were in the mid-1800s.

Out in the school yard enjoy the lush gardens. Check out the historic kitchen building, the wishing well, and, of course, the outhouse! Learn everything you need to go back to school here.

Ripley’s Believe it or Not! Odditorium

19 San Marco Avneue

Step into wonderous weirdness at Ripley’s Believe it or Not! Odditorium. Built in 1887 as a private winter home the stately castle became the Castle Warden Hotel. Illustrator, author, and world travelers Robert Leroy Ripley visited often. In 1950 the hotel became Ripley’s first Believe it or Not! Odditorium and has been captivating visitors ever since.

Visitors of all ages are welcome to explore this collection of over 800 rare and odd objects. Fan favorites include items from Ripley’s personal collection. He traveled the world in search of unique items including two-headed animals, shrunken heads, and other strange, shocking, and interesting treasures.

Brave visitors can even participate in weekend evening paranormal tours of the historic, and supposedly haunted, castle. Find out more about the Odditorium or reserve your spooky spot here.

My Tip: Unfortunately, due to time restraints, I did not get to visit this tourist favorite. But make sure you add this spot to your St Augustine road trip agenda.

The Old Jail

167 San Marco Avenue

It would be a crime to miss St. Augustine’s old jail. Built in 1891 by developer Henry Flagler the St. Johns County Jail housed prisoners from 1891-1953. In true Flagler style, the jail looked like one of his grand hotels from the outside. Inside was a different story.

Tour the former cells, learn about the history of the facility and what life behind bars was like in this historic site. Learn about life on the inside from historic reenactors and knowledgeable guides. Check out the collection of historic weapons and prison life artifacts.  

The Old Jail After Dark experience allows visitors 13 and over to participate in a hands-on paranormal investigation of this dark part of St. Augustine’s story. Come meet the spirits of what some consider the Old Town’s most haunted building. Plan your escape from, err, we mean to the Old Jail here.

Potter’s Wax Museum

31 Orange St

America’s first wax museum has been delighting visitors since 1949. Real estate mogul George L. Potter knew a fascinating find when he saw it. He established Potter’s International Hall of Fame in the model of European wax museums to bring historical and popular figures to life.

You won’t believe your eyes when you come face-to-face with replicas of your favorite celebrities. The craftsmanship of each of the 160 wax sculptures is mind-blowing. Film fans will appreciate “meeting” their favorite stars, including an entire section of horror movie icons! Get all the details for your visit to this unique collection.

My Tip: Bring your camera for lots of selfies! Here are a few of my favorites from my visit.

Lightner Museum

75 King Street

Enter an era of elegance and fine art in this beautiful Victorian-era Alcazar Hotel turned museum. Art lovers and history fans will enjoy the 132-year old building. Each of the five floors of the hotel have been restored and house a stunning collection of fine and decorative art. Fans of stained glass, Gilded Age opulence, and even antique musical instruments will be dazzled here.

Be sure to check out the café and shops situated in what was once the hotel’s original indoor swimming pool! Get enlightened about the Lightner Museum here.

Anastasia State Park

300 Anastasia Park Road, St. Augustine Beach

Head east to Anastasia Island to the tranquility of Anastasia State Park. Home to 1,600 acres of unspoiled beaches, nature trails, and spectacular sand, this is an isolated oasis for visitors and migratory birds.

Hikers can enjoy marsh trail tours offered by rangers, included with $8 (per vehicle) admission to the park. Kayakers will enjoy access to the many tributaries that enter the park from the inlet (rent kayaks or bring your own).

Campsites are available at the park (RV or tent). Each of the 139 sites include access to the beach.  Learn more about this seaside oasis here.

St. Augustine Lighthouse & Maritime Museum

81 Lighthouse Avenue, St. Augustine Beach

For over 100 years the St. Augustine Lighthouse on Anastasia Island has been guiding boaters to safety. Visit this iconic landmark for a fun adventure for the whole family.

Check out the historic buildings and see artifacts including items salvaged from area shipwrecks. Observe ship building and maritime archaeology demonstrations. Explore the beautiful grounds and nature trails.

Get your steps in with a climb to the top of the 175 foot tower. Bring your camera for amazing views of the Atlantic and the Matanzas River. Get all the details for your top-of-the-world adventure here.

Other things to do in Saint Augustine

Bridge of Lions

Medieval Torture Museum

Oldest House Museum Complex

Oldest Store Museum Experience

Villa Zorayda Museum

St. Augustine COVID Initiatives

As St. Augustine and surrounding areas of St. John’s County and the north east Florida region reopen information is frequently being updated to best meet the needs of the community and ensure safety for residents and visitors.

During this unusual time please travel safe. Check with your hosts, restaurants, and other venues in advance to learn their current plans and regulations.

Check here for Covid19 related safety updates and advisories: https://www.citystaug.com/812/Coronavirus-COVID-19 and http://www.sjcfl.us/coronavirus/

Plan Your Gay St. Augustine Road Trip

St. Augustine is a vibrant, interesting, and welcoming city. This diverse and historic town has something for every interest and budget. With over 500 years of history, this “Old Town” has some fascinating stories to share.

Wherever your gay St. Augustine road trip adventures take you, you’re certain to return home with great memories as part of your own his/her-story.

**Disclaimer: There is a good chance that this post contains affiliate or sponsor links. If you make a purchase through them, we may receive a small commission at no extra cost to you (for which we are extremely grateful).

Also, while we do our best to highlight LGBTQ-friendly destinations and businesses, info provided is based solely on personal experience and recommendations by community partners. We hope that nobody experiences discrimination or homophobia while visiting Florida, but we make no guarantees. Please inform us if you experience discrimination or homophobia while visiting any destination so we can make updates to our recommendations.

Events are subject to change. Please check the events webpage for updates and schedules.

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