Best gay staycations in the USA

Stefan Arestis

What if I told you that it’s possible to vacation in a way that completely bypasses all of the stress that comes with travel?

I’m talking about no excruciating packing, no tiresome drives, and no hectic airports. It sounds too good to be true, right? Well, put on your favorite cozy clothes and get ready to dive into the relaxing world of staycations!

Don’t get me wrong. I would not have made travel an essential part of my job if I didn’t love exploring every corner of the world with my darling Seby. But… I can also admit that there have been plenty of moments where, in the middle of tucking yet another tightly-folded shirt into my suitcase, I have wished that I could just take a break and spend time appreciating the comforts we have locally. This is what makes the concept of a staycation such a leisurely dream. By vacationing from home, you’re given the chance to save money, help local businesses, and unwind in a familiar location.

So, if you’re a queer person who lives in the United States and is currently wondering, “How do staycations apply to me?” then you’re in luck! There are tons of beautiful locations where gay citizens and travelers are welcomed with open arms – and I’m not just talking about big cities like New York or Los Angeles.

Some rural areas in the States heavily cater to their gay population, which is exactly what we want to highlight with this guide to the best gay staycations in the USA. So, if you live in or around any of these towns, prepare to be amazed at all of the glittering, gay wonders unfolding right outside your door!

Provincetown, Massachusetts

The name Provincetown might not mean much to the average person, but to any gay person living in the northeast region of the United States, it rings of LGBTQ history and freedom of expression.

Set at the very tip of Cape Cod and isolated from the majority of Massachusetts, Provincetown makes for the perfect holiday getaway. Considering the fact that the town has the highest rate of same-sex couples in the entire country, you will be warmly embraced at any time of the year. But trust me when I say that you will especially want to visit during the summer. Not only is Provincetown the best-known gay resort town on the east coast, but summer is the official party time for their LGBTQ community. With Provincetown Pride happening in June and the Girl Splash and Bear Week events occurring in July, you will be thrilled that you stopped by to experience this warm, beachy destination.

Above any gay parties and celebrations, you have to make sure that you spend time at The Atlantic House! As the oldest gay bar in the United States, it would be a shame if you didn't pop by for at least one drink. But with a small bar, a leather bar, and a nightclub all packed into one nautical-themed building… Let’s be honest, you’ll probably end up staying for a couple of drinks instead!

Of course, none of this goes to show their countless other gay businesses, their unofficial nude beach, or their ferry that can conveniently ship you right over to Boston if you wind up missing the excitement of a city. Provincetown, Massachusetts is truly a hidden gem and easily one of the best gay vacations spots in the world! If you live close enough to make this quaint town one of your common staycation spots, be sure to count your blessings!

Provincetown in Massachusetts is the perfect spot for a gay staycation in the USA
Provincetown is ready and waiting for your romantic beachside strolls…

Fort Lauderdale, Florida

When a city is considered to be the gay capital of its state, it almost feels like a challenge, right? It makes you stop and think, “Well, now I obviously have to check whether or not it lives up to the hype!” So, allow me to assure you right now that Fort Lauderdale completely fits the bill as an LGBTQ hotspot.

In terms of their population, Fort Lauderdale is second to Provincetown in their concentration of same-sex couples, and they see roughly 1.1m queer visitors each year! The streets of this beach city are lined with too many gay-friendly establishments to count, especially when you wander over to the nearby gay Wilton Manors area or even a bit further down the coast to sexy Miami.

Believe it or not, between Fort Lauderdale and Wilton Manors there are over 30 gay bars and clubs, each one more wild and dazzling than the last. Ramrod stands out as the oldest leather bar in the city, but we also highly recommend The Manor for its multiple dance floors and Rosie’s Bar and Grill for its hilarious dish names. I mean, come on, a fried pickle appetizer called the Britney Spears? That one still gets a laugh out of me when I think about it!

If partying isn’t your thing, then you’ll have a blast checking out the gay thrift store, Out of the Closet, or perusing either the World AIDS Museum or the Stonewall National Museum and Archives. And we can’t forget Pride events. Their official Pride hits the town in October, and it’s accompanied by the Outshine GLBT Film Festival. However, if you’re hoping to visit in the summer, Wilton Manors hosts a Stonewall Pride Parade and Festival in June that is well worth the trip.

Please, do not let me stop you from checking it out yourself if I haven’t been convinced you enough that Fort Lauderdale is the definitive gay capital of Florida. Just be sure to write me a thank you card describing the fantastic time you had in the sunshine state!

Alibi Monkey Bar is one of the oldest and largest gay bars in Fort Lauderdale, with lots of events like drag shows and karaoke
A night out in the gay bars of Wilton Manors

San Juan, Puerto Rico

Many people don’t seem to know this, but Puerto Rico is technically a territory of the United States. This essentially means that you don’t need a passport to travel there, you can use your American dollars while visiting, and, best of all, in my opinion, it's an extremely gay escape located in the Caribbean.

Being off the mainland and resting on tropical waters, Puerto Rico is a fabulous destination all year round. Specifically, San Juan is home to the most phenomenal LGBTQ stops in the country, including the gay-friendly Condado Beach and the occasionally cruisey Ocean Park Beach. However, if you’d prefer to avoid the ocean waves and sandy shores altogether, then you can easily head into either the tourist district of Condado or the neighborhood of Santurce to witness the most concentrated gay areas the town has to offer.

San Juan Pride swings through the streets during June, but the party never stops with their lively array of bars and clubs constantly keeping the atmosphere alive. Cinco is the largest gay club in all of San Juan, and it is best known for its drag performances and drag bingo, which offers some rather scandalous prizes. Though, if you’re searching for the best place to host your naughty night out, you’ll probably want to hit up SX. Their dancers… Well, to put it simply, nobody does it better than those gorgeously tanned Puerto Rican boys!

San Juan may be different than what you’d expect from your average staycation, but there are countless queer places worth exploring and even more leisurely activities beckoning on this stunning island!

Puerto Rico is our top pick for the most gay friendly island in the Caribbean
The Puerto Rico boys hanging out on the Condado gay beach

Fire Island, New York

Have you ever wanted to experience life in America’s first gay and lesbian town? Then look no further than Fire Island, New York. Their meek population of 310 people mostly consists of gay men ranging from 20 to 50 years old, which should bring you plenty of comfort and reassurance that your stay will be nothing but pleasurable.

Despite being a mere two hours from Manhattan, Fire Island feels like a distanced world of its own invention. Everyone on the island appears to follow a strict, unspoken schedule that you will definitely want to be mindful of throughout your visit. While that may sound stressful, don’t worry one bit! This schedule just gives you a decent excuse to chat with the friendly locals, especially those residing in either the Pines neighborhood or the Cherry Grove neighborhood.

Both areas serve as popular sites for the LGBTQ community, but they do have their own distinct vibes. With the Invasion of the Pines and the Fire Island Pines Party happening in July, it’s easy to see why the Pines is considered the party hub for gay boys. Meanwhile, Cherry Grove maintains a comfortable, down-to-earth aura for its guests. And in between the two, you will find a delectable strip of forest known as the meat rack. I don’t think I need to give many more details aside from the name, but…it is the perfect spot for canoodling with your lover.

In the end, the Pines and Cherry Grove both have terrific gay beaches as well as thrilling gay bars, like The Blue Whale and Ice Palace. So no matter which one you choose, you will have everything you could possibly need from your Fire Island staycay!

Key West, Florida

“One human family.” That is exactly how Key West, Florida brands itself to guests, so it comes as no surprise that the city is regarded around the world as an LGBTQ paradise!

Located at the southernmost tip of the United States, Key West stands out as a destination small in size but large in character. While the other communities along the Florida Keys share a similar tropical ambience, none can even begin to match the eccentric people or the exhilarating activities found in Key West.

Duval Street, which is also known as the Pink Triangle, will be the number one place to hit up during your staycation if you’re looking to enjoy a fun night on the town. The popular bars 801 Bourbon, Aqua, and Bourbon Street Pub comprise the three corners of the triangle, each has its own unique appeal. Aqua, for instance, is best known for its nightly drag shows. On the other hand, 801 Bourbon offers everything from bingo to karaoke, and Bourbon Street Pub showcases the spiciest male dancers.

And best of all? The gay party in Key West lasts all year with their seemingly never-ending Pride events! From February to April, the city hosts gay spring break for LGBTQ students. June sees the official Key West Pride, which is then followed by the Tropical Heat adult party in August and Womenfest in September.

That’s not even to mention their gorgeous beaches, like Higgs Beach and Smathers Beach, or the Mallory Square Sunset Celebration. Key West has the complete, carefree package for your high-quality holiday!

The rainbow crossing on Duval Street in Key West is the heart of the island's awesome gay scene
Our gaycation out on the Pink Triangle of Key West

Palm Springs, California

Ah, the lovely Palm Springs! Better known across the globe as America’s Great Gay Oasis. You knew we couldn’t leave this Californian beauty off our list.

Not only does Palm Springs boast about the 330 days of sun they see every year, but they also hold the title of having the largest concentration of LGTBQ resorts in the entire Western United States. But hang on folks because it doesn’t stop there! The city has also stated that their gay population comprises over 50% of their annual population, that they have the highest per capita gay population, and that they have the fifth-highest percentage of same-sex households. Pretty impressive, right?

So, now that you’ve heard about their fantastic accolades, allow me to describe a handful of their tantalizing establishments and events! The bars in Palm Springs are to die for, seeing as how each of them seems to embrace a super cute theme. Toucan’s Tiki Lounge, for example, is best known for hosting the longest-running drag show in Greater Palm Springs, but it is also commended for its commitment to an outstanding tropical aesthetic. Streetbar, which is arguably the best karaoke joint in the area, rocks a more retro style, and Stacy’s Palm Springs throws its patrons back to the days of intimate jazz clubs.

The Greater Palm Springs Pride Celebration hits the city in November, which is rather late in the year as compared to other states. However, they make up for their tardiness with the size of the party itself. Aside from the typical parade and wall of vendors, Palm Springs Pride additionally welcomes the Palm Springs Golf Classic, the Stonewall Equality Concert and the Broadway in Drag Pageant.

If you somehow find yourself longing for more riotous nightlife and adventure, LA is about a two hour drive away, but I guarantee you will not find the same level of queer entertainment there!

Palm Springs in California is pretty much a gay paradise and perfect for a gay staycation
Palm trees, sun and gay resorts – Palm Springs sure sounds like Heaven to us!

San Francisco, California

The only city in California that could possibly hold a candle to Palm Springs in terms of LGBTQ prominence and history is San Francisco. Known as the original gay-friendly city as well as the gay capital of the world and the gay Mecca… I mean no offence to anyone in Palm Springs, of course, but San Fran is obviously a really big deal!

Historically, The Castro District has been the premiere gay hotspot in all of San Francisco, but over the past few years Noe Valley, Bernal Heights and the Mission District have all stepped up as possible contenders for the favorite gay neighborhood. With approximately 15.4% of the city’s population being comprised of gay individuals, it’s definitely understandable why they would feel the urge to expand. And it also helps to explain how one place could hold so many Pride events in just one year!

San Francisco Pride, which has been dubbed the largest gathering of LGBTQ people and allies across the States, sweeps through San Fran at the end of June. Also in June is the Frameline Film Festival, which is known as both the largest and oldest LGBTQ film festival in the world. Then, there’s the world’s oldest transgender film festival, the San Francisco Transgender Film Festival, during November and the infamous Folsom Street Fair for BDSM and leather subculture during September. If you don’t mind a little travel during your staycation, you could also venture out to Sonoma in February for the Out in the Vineyard wine weekend. And, believe it or not, that’s just naming the biggest ceremonies!

Now, to name the best of the best in San Fran attractions, the Pink Triangle Park honoring queer victims of the Nazi regime, the GLBT Historical Society Museum and the San Francisco South of Market Leather History Alley are brilliant places to spend an afternoon. Once night falls, you can hit up one of the city’s finest bars like the Hi Tops sports bar or the SF Eagle Biker Bar.

There is never a dull moment in San Francisco, so if you’re fortunate enough to be spending your staycay in this remarkable city, be sure to take advantage of your surroundings!

Honolulu, Hawaii

Though Hawaiian gay life may feel more subdued than that of the mainland, you will undoubtedly be celebrated in this rainbow state! Honolulu, above any other part of the island, welcomes their guests to take part in the local LGBTQ culture.

If you’re searching for the center of gay activity within Honolulu, Waikiki Beach will be your go-to spot with Queen’s Surf Beach serving as a small subsection. There you will find a majority of the gay nightlife, which is absolutely unforgettable! Scarlet Honolulu is one of the largest bars in Oahu that caters to the queer community, making it a must-stop location when you’re wanting a tasty drink and a hot dance floor. It should also be noted that Hula’s Bar and Lei Stand provides prime entertainment with both drag shows and male dancers. Similarly, Bacchus Waikiki serves up terrific deals and offers guests the opportunity to kick back and relax on shirtless nights. Also don't miss out on Little Beach – one of our favourite gay beaches in the world.

As for events, Honolulu Pride kicks off in October, but if you would prefer to observe Pride Month in June, there is also a Pride Community Picnic which includes free food, drinks and games. I honestly can’t think of a more perfect way to become acquainted with a group of people than bonding over a meal, so you would certainly catch me among that crowd! Other not-to-miss gay events in Hawaii include Splash, the gay pool party hosted in July and the Honolulu AIDS Walk in April.

Honolulu, Hawaii is clearly a perfect vacation destination for any occasion, so there should be no shock that it stands as an equally pleasant place to live up your staycation. Feel free to head out and relax on those beautiful shores!

Hawaii is a stunning spot for a gay staycation in the USA, particularly Little Beach
Who's ready to get wet?!

For more inspiration:

These are the best places in the USA for a gay staycation

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