St. Augustine may be the oldest city in the U.S., nothing about it feels outdated and she’s aging like a daddy gay in an Abercrombie shirt on retinol. With Spanish flair, delicious eats, swoon-worthy architecture, and a dash of spooky camp, a queer-friendly atmosphere, this historic gem is one of Florida’s most unexpectedly delightful LGBTQ+ travel destinations. Whether you’re here for history, flavors, beaches, or a little moonlit mischief, this coastal charmer delivers.
Where to Stay: Casa Monica Resort & Spa
Casa Monica Resort & Spa blends Moorish architecture with luxurious boutique design for a stay that feels glamorous, comfortable, and unmistakably stylish. Think ornate archways, chandelier glow, and rooms you actually want to lounge in between adventures. The hotel sits steps from the historic district—perfect for morning strolls, late-night bites, and that all-important “outfit check” in the lobby mirrors. Its central location places the entire historic district within easy reach.
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The view from my room -
The bed was hard to leave -
the room was not the traditional square space -
Hotel Lobby -
Front desk -
Campagne on arrival -
Complementary throne? -
Poolside. -
The dark clouds did roll in one day but we stayed in the pool. -
Breakfast at the hotel restaurant was easy and tasty -
Breakfast at the hotel restaurant was easy and tasty -
Breakfast at the hotel restaurant was easy and tasty -
The hotel bar was hopping every night -
with great bites -
and dessert -
and liquid dessert
The room was so comfortable, the robe was lush and wrapped around you, not letting you leave. The view outside my window was one of the museum’s garden area in the center of town, which was across the street from Flagler College, also part of my view.
Definitely explore the pool area as not oly are the drinks plentiful but the people you meet while soaking up the rays and shade, honestly, I have not had a better conversation around a body of water in a long time. we all talked about our lives, I’m openly gay, manage a gay magazine, and that was accepted and part of the conversation with individuals from Minnesota, Tennessee, Georgia, Southern Florida. The pool was a great communal area, right on par with the lobby bar down stairs.
What to See: History With Heart and Heritage
St. Augustine’s layered history—spanning Indigenous communities, Spanish colonization, African heritage, and early American culture—gives it a depth that resonates strongly with LGBTQ+ travelers. All subtitles below are hyperlinks to learn more about the location.
Castillo de San Marcos
Explore the oldest masonry fort in the U.S., complete with waterfront views, cannon firing demonstrations, and stone passageways. If there is a tour available when you go, take it! It was one of the best and informative historical tours I’ve taken of an individual setting.
Be sure to wear the sunscreen and maybe bring a fan for even in the shade and with a breeze off the water, it was quite toasty.
Fountain of Youth Archaeological Park
Sip from the legendary spring and wander through an expansive archaeological park that uncovers the city’s early history. Grab a cup, fill it up, drink the “legendary waters” and pretend it’s reversing your last Pride weekend.There was a park member in the shed where the fountain is. Once again, an amazing educational experience listening to her.
Should you sip form the fountain? For historical purposes, yes, but for taste and refreshment, no. Not sure what the taste was, but it was not the purified water we are used to. The lush grounds and exhibits make this tourist stop more than a gimmick, though—this is the actual site where European settlers first arrived. Enjoy the gardens and the gift shop. I would say it is a definite must to say you have gone.
Mission Nombre de Dios
A serene bayfront landmark significant to some of the earliest Catholic history in North America.
On September 8, 1565, Spanish Admiral Pedro Menéndez de Avilés landed on the shores of what is now St. Augustine, Florida, and claimed the land for both Spain and the Catholic faith. Accompanied by priests, he celebrated the first permanent European settlement in what is now the United States.
Mission Nombre de Dios and the National Shrine of Our Lady of La Leche stand as living witnesses to that sacred beginning. The Historic Chapel, Rustic Altar and Great Cross mark the site where faith first flourished on these shores and continue to draw pilgrims seeking grace, peace and renewal.
I was raised Roman Catholic, but I also taught world religions for years so I can appreciate the belief structure, the history or religions. This was a beautiful monument with a 208 foot tall cross, an beautiful small chapel, gravestones and gardens. Even if you’re not religious, the history—and the gigantic cross overlooking the bay and a landmark that you will see from every part of St. Augustine—is worth the moment of awe. St. Augustine is full of historical sites and this is another one you should see to learn more about Florida history and a great deal of US History you did not know.
Fort Mose Historic State Park
The first legally sanctioned free Black settlement in what is now the United States. The new fort replica and museum create a powerful, emotional, and important historical experience—especially meaningful for LGBTQ+ travelers who appreciate stories of resilience and liberation.
St. Augustine was here when the US started out, it was here for it’s trials of slavery and independence. To learn the acceptance of the Spaniards toward free black individuals, and even how the Spaniards invited them to go with them when they left Florida and how this affected Caribbean demographics was energizing for this previous history educator to learn.
Fort Matanzas
A free ferry ride leads to this scenic historic watchtower surrounded by pristine nature. The ticket is free, but you need to schedule your trip in advance and make the appropriate reservation. St. Augustine is fort happy, history happy, but honestly, it was neat to se and hear about.
Best Places to Take Photos
- Castillo de San Marcos fort walls
- Casa Monica’s ornate lobby
- Bridge of Lions at sunset
- The deck of the Schooner Freedom
- Flagler College courtyard
- Villa Zorayda’s interiors
Where to Eat: A City Full of Flavor
St. Augustine excels in culinary variety—Spanish, Cuban, Southern, and coastal influences blend beautifully across its restaurants.
Columbia Restaurant
A beloved historic spot offering Spanish-Cuban classics. The 1905 Salad is iconic. Our table was round and our bellies were rounder when we left as all the options we enjoyed were delicious and filling. Be prepared for some great service and great flavors at a historic location.
Smokin’ D’s BBQ
Fresh, slow-smoked meats prepared daily. Rustic, hearty, and unforgettable.You can forget about eating inside as the business is petite but they flavors are massive. We saw the pit master carve delectable delights, wrap them in butcher paper, shove them in a bag, and we unwrapped all that as well as cracked open containers of sides at the picnic table outside. Sticky goey saucey awesomeness. We all had our favorites.
PK’s Roosevelt Room
A top-tier brunch destination with housemade dishes and zero freezers in use. Handmade eggs Benedict, salmon boards, fried chicken biscuits…the kind of comfort food that fuels a day of walking, shopping, cruising, and other-ings. Some of the best hospitality was here as our server was on task and on target. we loved our interactions, but then the food came out. Brunch stands for “you shouldn’t eat all of this, but it’s too good to stop”, right? Put this on your list, make a reservation just in case as this place is not open for dinner.
Paladar Cuban Café
Perfect for quick Cuban pastries, sandwiches, and strong cafecito. The problem is, we did not want to leave this tiny little eatery. The drinks were inventive, the pasteries were true to the culture, and the food was made to our specifications and we had many. The staff was very yummy to look at too. Can I say that? Yes, I can and did, btu honestly, this is a fun offering that seems family operated. Keep an eye on their website as I think there was rumor of some movement or opening another location closer to town.
The Cellar Upstairs
Rooftop dining with live music and an impressive wine list. You could walk here from downtown but we enjoyed the 4-minute ride and then the elevator up to the top floor. Many of the other places we went to were in the heart of St. Augustine as it is such a wonderful walkable city. The Cellar Upstairs was slightly removed from downtown so it felt like a whole new experience.
The staff was impeccable with their knowledge of the dishes, the ingredients, the wine list, and the suggestions they made were spot on. I love someone who takes pride in their service and their hospitality and the staff at The Cellar was spot on and a true wow. Food was right in line with the service and the evening meal was a hit.
Lynda’s at the Ocean Club
A breezy, beachfront brunch ideal for relaxed coastal afternoons. So this was a drive from town, out along the shore. Pulling up, it seemed like we were going to an exclusive location where the uppity people went. We’d be fine with that, but we were in shorts and sandals and that turned out to be perfect for this brunch with ocean views. Was it bottomless mimosas of varying flavors?
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The Cellar Upstairs -
The Cellar Upstairs -
The Cellar Upstairs -
The Cellar Upstairs -
The Cellar Upstairs -
The Cellar Upstairs -
The Cellar Upstairs -
The Cellar Upstairs -
The Cellar Upstairs -
Lynda’s at the Ocean Club -
Lynda’s at the Ocean Club -
Just outside Lynda’s at the Ocean Club -
Casa Maya -
Casa Maya -
Casa Maya -
Casa Maya
Casa Maya
Mexican cuisine with fresh ingredients and warm hospitality—get the guac and thank me later. Even downtown, you can still find some quiet and intimate settings. We ate upstairs at Casa Maya where the table quickly became loaded with appetizers and entrees. Make sure you’re okay with eating off each other’s plates as you’ll want to try everything on the table.
LGBTQ-Friendly Cocktail Spots
- Ice Plant Bar – craft cocktails and industrial-vintage vibes
- Casa de Vino 57 – cozy wine garden
- Odd Birds Bar – lively and creative
- The Cellar Upstairs – perfect rooftop atmosphere
What to Do: Culture, Romance & Waterfront Adventures
Haunted Boat Tour
A moonlit boat tour with ghost stories and scenic nighttime views. It was cute in a straight campy way. It was just great to be out on the water.
There was a great deal of history too on this excursion, besides the splashing of spookiness. Seeing the city at night from the water was a new experience to share with friends and ghosts.
Sunset Sail on the Schooner Freedom
The city’s only tall ship offers a romantic and peaceful sunset sail. Open bar, bay breezes, dolphin sightings, shark fins making their way across the water, beach views, and spectacular sunsets. Lots of romance or relaxation could happen here and it did.
St. Augustine Lighthouse & Maritime Museum
Climb to the top for panoramic coastal views. Well, you can also look up from the bottom to the top, too. Lots of mini buildings peppered the property housing some lighthouse information, archeological findings, boat making, and war history. All very easy to navigate, and if you wanted to go to the top to get a view, by all means, take the hike.
Architecture & Cultural Highlights
Flagler College
A former luxury hotel, the Hotel Ponce de Leon, was transformed into Flagler College featuring Tiffany stained glass and Gilded Age artwork. It was one of the first buildings in the United States to be wired for electricity when it was completed in 1888. Henry Flagler, a friend of Thomas Edison, had the electrical systems installed by Edison’s company, providing power to the luxury hotel before places like the White House had it.
Our youthful tour guide was a fellow gay, mentioned his husband a couple of times, and kept the tour energetic, funny, and informative. I would say this was a highlight of the weekend, too. Wait until you see the rotunda as well as the dinning hall with, yes, those Tiffany windows, too many to count.
Villa Zorayda Museum
Inspired by Spain’s Alhambra, this museum showcases ornate design and eclectic artifacts. Loved loved loved the self-paced private audio tour that let you meander around the museum and enjoy what you wanted to at your own pace.
Some things I would have loved to have taken home, but alas, they needed to stay there for the next gay to covet. No, it wasn’t the Egyptian foot missing a toe, but some other odd, quirky and luxurious things. Some rooms we could not take pictures in.
St. Augustine Distillery
Tour a beautifully restored industrial building producing top-quality craft spirits. Yes, this is both an architectural and cultural highlight.
You get to tour the distillery, but you also get to taste a good amount of the goodies, if you pay for the tasting tour. There are a variety of tours so choose wisely.
What to Pack (Gay Traveler Edition)
- Linen shirts and breathable fabrics
- A stylish outfit for the sunset sail
- Your best brunch look
- Swimwear for beach days
- SPF protection
- Comfortable, stylish walking shoes
Where to Relax: St. Augustine Beaches
St. Augustine Beach – classic, wide, and great for swimming.
Vilano Beach – calm, scenic, ideal for long walks.
Ponte Vedra Beach – pristine and upscale.
Queer Appeal: Why Gays Love St. Augustine
You feel it immediately: St. Augustine is a city built on layers of cultures, stories, and reinvention—something queer travelers connect with. Add in walkability, waterfront charm, and architecture that swings from Moorish fantasy to Caribbean breezy, and you’ve got major LGBTQ+ weekend potential.
And while it’s not a “circuit-party town,” it’s a destination that welcomes queer travelers with warmth, history, and the kind of romantic backdrops perfect for couples (or meet-cutes).
While riding up in the elevator at the Casa Monica Resort, we met a groom who just got married to his now husband. They were from Jacksonville, Florida but have loved St. Augustine forever. If you know Florida, many of us say anything north of Orlando is just Southern Georgia, which may mean it is not as liberal as the areas that house Orlando, Tampa, Fort Lauderdale, Miami, Key West. So it was great to hear from this man, now husband, and that they chose St. Augustine as the place to say their vows.
He did share that there were some reservations about one part of the blessed day. They planned an open-carriage ride through downtown. Two grooms in a carriage in tuxedos in any city in America may be a sight to see, but not always accepted. He said it went very well! And the staff at the wedding venue was beyond welcoming, accommodating, and supportive. He was beaming talking about it as well as you could feel his relief that the day went well in any city USA.
It does feel like a very white, very straight city, there’s no denying that. But to hear this groom’s story and to have the nice and open experiences we had. St. Augustine is worth a look for history, romance, and relaxation.
Great Time of Year to Visit
Its location on the Florida Coast means that St. Augustine is a great place to visit any time of the year, but right now, there’s an explosion of light and energy.
St. Augustine Nights of Lights is an annual holiday festival where millions of white lights decorate the historic downtown from mid-November to January. The event transforms the city with illuminated buildings, bridges, and palm trees, attracting crowds for viewing and tours.
About the Nights of Lights festival:
- Duration: The event typically runs nightly from mid-November through early January. For the 2025-2026 season, it runs from November 15, 2025, to January 11, 2026.
- What it is: It is an award-winning display where millions of white lights adorn historic buildings, rooflines, palm trees, and other features of the city, creating a magical winter wonderland.
- What to do: Visitors can walk through the illuminated streets, take a narrated trolley or horse-drawn carriage tour, or see the lights from various vantage points, including the bayfront.
- Popularity: It is a very popular event that attracts a lot of people, especially on weekends. For a less crowded experience, consider visiting on a weekday or in the first couple of weeks of December.
- Key locations: Some of the most popular areas for lights include Flagler College, the Lightner Museum courtyard, St. George Street, the Bayfront, and the Bridge of Lions.
Final Thoughts: A Coastal Gem With Queer Charm
St. Augustine offers a unique blend of culture, architecture, culinary excellence, and coastal beauty—all wrapped in a genuinely welcoming atmosphere for LGBTQ+ travelers. It’s intimate, historic, and effortlessly romantic.
Whether you’re exploring solo, traveling with friends, or planning a couple’s retreat, St. Augustine delivers charm, depth, and unforgettable moments.
This city may be historic, but she’s absolutely timeless.
Here’s some extra pics of the weekend.
