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Gay Retreats USA
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The USA is a vast country with incredibly diverse landscapes and climates. Naturally, it’s home to many excellent retreats for gay travelers.
You’ll find hugely popular gay retreat destinations, such as Provincetown and Key West – both of which attract many gay travelers in peak season.
You’ll also find excellent gay-popular resorts dotted all over the USA in more remote locations.
We’ve gathered together a collection of some of our favorite gay retreats in the USA. Some are destination retreats surrounded by stunning landscapes.
Others are located in popular vacation towns and cities.
Gay Retreats USA
Gay Retreats USA
Provincetown is packed with excellent gay retreats. It’s a small town in Massachusetts on the tip of Cape Cod. It became a favoured haunt of artists and later LGBT+ travellers. It’s also famed as the site of the Mayflower landing. You’ll find excellent gay retreats in the centre of town. There are also many boutique options dotted around Provincetown in more remote locations. Provincetown has been a top gay retreat for many decades.
Also in Cape Cod you’ll find the exclusive island of Martha’s Vineyard. It’s a charming place and it’s an ideal spot for a gay retreat vacation. There are no gay-specific hotels but the island is very liberal. You’ll find many old-world boutique properties. Martha’s Vineyard has less of a party-vibe than Provincetown but it’s great for a romantic vacation.
Key West is one of the best places for a gay retreat in the USA. It’s located in one of the most remote parts of the country. It has many gay retreats. You’ll find a buzzing gay scene on Duval Street. Key West has some fabulous retreats, including secluded luxury hotels on little islands. It’s also a popular destination for artists. The famed LGBT writer Tennessee Williams used to live in Key West.
Santa Barbara California
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Gay Provincetown Travel: Gay Bars, Hotels, Culture & History
Provincetown is the best small-town destination for gay travelers in the USA. It's long been hailed as one of the most liberal towns in the country, and it's a big draw for artists and bohemians: gay-popular hotspots tend to begin as artist hotspots. Think Mykonos, Key West and Sitges.
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Anthony Dowlatshahi set out on a pretty wild gay adventure in Alaska. We couldn't resist getting in touch to see how it all went. It turns out that there's more to America's coldest state than huntin', shootin' and fishin'. As Anthony explains, Alaska has some of the world's most breathtaking landscapes, perfect beer and surreal midnight sun. What would you say were the best highlights of your trip?
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The Hacienda At Warm Sands is a luxury gay male retreat in Palm Springs. Surrounded by desert landscapes, it’s a luxury resort comprised of 10 suites. It’s widely considered to be one of, if not the most luxurious gay retreat in the USA. An ideal place to combine with Los Angeles.
Sunset Key Cottages is the most luxurious resort in Key West. It’s located on a private island a mile from the coast of Key West. It’s just 15-minutes away by ferry. It’s a great choice for a gay retreat. You can enjoy all the action in Key West and then retreat to the privacy of your luxury cottage.
The San Ysidro Ranch is one of the most luxurious retreats in the USA. Located at the foot of the Santa Ynez Mountains in Montecito, Santa Barbra, you’ll count Oprah as a neighbour for the duration of your stay! It’s surrounded by stunning manicured lawns. This is a very peaceful and romantic retreat. It’s just a 20-minute drive to central Santa Barbra.
Head to Provincetown if you want to party
2Head to Martha's Vineyard or Nantucket for luxury seclusion
3Head to Key West for a party atmosphere and luxury retreats
Palm Springs California
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Private Group Retreat in Sri Lanka
Tailor-made VacationThis expertly crafted seven-night Sri Lankan getaway is designed to make group travel to Sri Lanka easy. This is your chance to experience a private villa vacation built entirely around your group, where every detail has been thoughtfully planned. You will stay at a gorgeous and well-positioned property called Kirana, A Santani Villa. Overlooking serene Bentota Beach in Sri Lanka, this villa was designed by renowned architect Channa Daswatta.
8 days tailor-made from $3,125 per person View trip
Sri Lanka & Maldives Wellness Journey
Tailor-made VacationEmbark on a wellness journey that combines Sri Lanka's cultural beauty with the tranquil luxury of the Maldives. This luxury wellness itinerary allows you to rejuvenate mind, body and soul, all whilst discovering two of the world's most tranquil destinations. Start amidst Sri Lanka's lush hills at Santani Wellness Kandy, where tailored programs rejuvenate mind, body, and soul.
17 days tailor-made from $12,595 per person View trip
Sigiriya to Ella: A Journey Through Sri Lanka’s Cultural Triangle and Tea Country
Tailor-made VacationSri Lanka carries three distinct landscapes within a few hours' drive of each other, ancient rock fortresses, misted tea hills, and a wildlife-dense southern coast, which is what makes it one of the few destinations where a single trip can move through this much variety without feeling rushed. This 15-day itinerary was built by our travel specialists around that range, moving from the Cultural Triangle's ancient sites through tea country to the coast.
15 days tailor-made from $7,440 per person View trip
Luxury Mykonos & Santorini Group Trip
Tailor-made VacationSpend seven days island-hopping between two of Greece's most iconic destinations. This trip strikes the balance between high-energy Mykonos and romantic Santorini — perfect for groups who want both nightlife and natural beauty. Your group stays in a private villa within walking distance of Mykonos Town's winding streets and whitewashed buildings.
7 days tailor-made from $3,565 per person View trip
Private Gay Group Villa Escape in Tuscany
Tailor-made VacationThis seven-day luxury gay group escape is built around Villa Ardore, an eight-bedroom private estate surrounded by vineyards and rolling countryside. Sleeping up to 18 guests, it is ideal for a group of friends, couples, milestone birthdays or a celebration that deserves something more memorable than a hotel. The appeal is simple.
7 days tailor-made from $5,880 per person View trip
Private Countryside Castle Getaway
Tailor-made VacationImagine having an entire castle to yourselves. Picture your group raising glasses as the sun sets over ancient battlements, or gathering around a roaring fire in a great hall that has hosted royalty for centuries. This isn't just accommodation - it's your private kingdom for four unforgettable days. Experience the UK as you've seen it in the movies. Completely Bespoke. Effortlessly Organized. Every detail is tailored precisely to your group's vision.
4 days tailor-made from $3,260 per person View trip
Luxury Family Maldives Getaway
Tailor-made VacationEmbark on an enchanting journey to the Maldives with your family on this meticulously designed 10-day itinerary. We've curated a symphony of exclusive experiences, tailor-made to cater to both the young and the young at heart. Your journey begins at Soneva Fushi, an island where luxury meets adventure.
9 days tailor-made from $10,970 per person View trip
Family-Friendly South Africa Safari: Big Five & Beyond
Tailor-made VacationEmbark on an unforgettable luxury family safari in stunning South Africa. This carefully crafted 10-day itinerary takes you and your loved ones through the heart of South Africa's most renowned game reserves, offering an unparalleled opportunity to connect with nature and each other in the most luxurious settings. Your adventure begins at the prestigious Chitwa Chitwa in the Sabi Sands Game Reserve.
10 days tailor-made from $5,445 per person View trip
Costa Rica Family Escape
Tailor-made VacationEmbark on an unforgettable journey through the heart of Costa Rica with our bespoke luxury family itinerary, designed to deliver both exhilarating adventure and pure relaxation. Over nine days, this tailor-made experience will take you from the awe-inspiring Arenal Volcano to the serene beauty of Manuel Antonio, and is ideal for families seeking an extraordinary Costa Rican adventure.
9 days tailor-made from $4,255 per person View trip
Classic France by Train
Tailor-made VacationDiscover French elegance and culture on our Classic France by Train itinerary. This 10-day journey invites you to immerse yourself in the heart of France, traversing from the romantic boulevards of Paris to the culinary capital of Lyon, and finally to the sun-drenched Riviera in Nice.
10 days tailor-made from $3,940 per person View trip
Italy & Dalmatian Coast Cruise
Tailor-made VacationVenice's canals, a string of Adriatic ports, and Rome's oldest streets, seen at the pace only a ship allows. This tailor-made itinerary and Seabourn gay cruise pairs Italy with the Dalmatian Coast, moving from Venice's canals to a string of Adriatic ports before closing in Rome.
15 days tailor-made from $10,045 per person View trip
Northern Europe Voyage
Tailor-made VacationEmbark on a luxurious Northern Europe voyage that seamlessly combines the historical splendor of London with the untouched natural beauty of Scotland and Iceland. Your journey begins in the bustling heart of London, staying at the iconic Claridge's Hotel, where British elegance and a rich history set the tone for your adventure.
13 days tailor-made from $7,410 per person View tripFrequently asked questions
What does Out Of Office do?
Out Of Office is a luxury LGBTQ+ travel company specializing in tailor-made vacations and extraordinary journeys around the world. We create bespoke luxury vacations, LGBTQ+ honeymoons, safaris, cruises, beach escapes, private tours and group trips, with every itinerary designed around you. Our travel specialists combine global expertise, first-hand destination knowledge and trusted local partners to create seamless, highly personalized experiences.
Is Out Of Office a gay travel agency?
Out Of Office is an LGBTQ+ owned and run luxury travel specialist, with particular expertise in gay and LGBTQ+ travel. We understand the additional considerations that can come with traveling as an LGBTQ+ person or couple, from local laws and customs to finding genuinely welcoming hotels and experiences.
We welcome every traveler, including friends, families and allies. Many of our clients are not members of the LGBTQ+ community, but choose Out Of Office for our luxury travel expertise, personalized service and discretion.
Do you create tailor-made LGBTQ+ vacations?
Yes. Every tailor-made trip with Out Of Office is designed from scratch around your interests, travel style, budget and the way you want to experience a destination. We can arrange luxury hotels, private transfers, flights, guides, excursions, cruises and special experiences as part of one personalized itinerary. The journeys shown on our website are there to inspire you rather than restrict you; only clearly identified group departures operate as fixed itineraries.
How do you choose LGBTQ+ friendly hotels and destinations?
We combine first-hand destination knowledge with trusted local expertise to recommend luxury hotels, resorts and experiences where LGBTQ+ travelers can feel informed and welcome. We also consider the laws, customs and attitudes of each destination, because LGBTQ+ rights and experiences differ around the world. Our team regularly visit many of the properties we work with and where a destination requires greater awareness, we give you clear and considered advice so that you can make an informed decision about where and how you travel.
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We plant trees for every booking
For every booking made with Out Of Office we commit to planting trees in your name to help reduce the impact of travel on future generations. You'll even get a link to see where your trees are planted in the world via our partner Ecologi.
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Rainbow Railroad helps LGBTQ+ people escape state-sponsored violence and persecution. A donation goes with every trip we sell, funded by us and never added to your price.
Start Planning Your Trip
Tell us where you would love to go, when you are thinking of traveling and what kind of trip you have in mind. One of our LGBTQ+ travel specialists will create a tailor-made itinerary designed around your destination, style and preferences.
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