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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 travellers.
You’ll find hugely popular gay retreat destinations, such as Provincetown and Key West – both of which attract many gay travellers 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 favourite gay retreats in the USA. Some are destination retreats surrounded by stunning landscapes.
Others are located in popular holiday 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 travellers 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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Customer Interview: Alaska Adventure
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?
ReadThe Best Hotels for a Gay Retreat
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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Best Gay Honeymoon Destinations 2027 & 2028
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Costa Rica Family Adventure
Tailor-made HolidayEmbark on an unforgettable journey through Costa Rica, where your family will experience thrilling wildlife encounters, breathtaking landscapes, and immersive cultural experiences. From exploring misty rainforests and spotting sloths in the treetops to learning to surf on golden beaches, this itinerary balances adventure and relaxation, ensuring every member of the family has a magical experience. Your adventure begins in Tortuguero National Park, a remote jungle paradise accessible only by boat.
11 days tailor-made from £4,200 per person View trip
Ultimate Luxury: Costa Rica
Tailor-made HolidayFrom lush jungles to the pristine coastline and cloudforests, this exclusive Costa Rican adventure is designed for those who seek the extraordinary. Over the course of this journey, you will immerse yourself in the country’s vibrant landscapes, encounter exotic wildlife, and experience the ultimate in eco-luxury. Your luxurious adventure begins at Finca Rosa Blanca, a boutique coffee estate where you can unwind amid rolling plantations and sip freshly brewed coffee with sweeping valley views.
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Classic Costa Rica Tour
Tailor-made HolidayDiscover a classic journey through Costa Rica, immersing you in untamed rainforests, volcanic landscapes, and pristine beaches. You will experience the vibrant streets of San José, the remote jungles of Tortuguero, the volcanic hot springs of Arenal, the mystical cloudforests of Monteverde, and the sun-drenched shores of Santa Teresa.
13 days tailor-made from £5,100 per person View trip
Historic Ireland Tour: Dublin, Kilkenny & County Clare
Tailor-made HolidayThis is not your typical Irish adventure. It is Ireland's history experienced alongside true luxury, where centuries-old castles meet grand estates, and every experience feels personally crafted for you. The trip opens in Dublin, though not the version most visitors see. An electric bike replaces the walking tour, private access replaces the queue at the castle gate, and the city's growing reputation as a food destination gets room to show itself.
10 days tailor-made from £8,950 per person View trip
Tour of Ireland: Dublin to The Cliffs of Moher
Tailor-made HolidayThere is something truly magical about Ireland—a land where ancient stories whisper through the winds, where every cobbled lane and rolling green hill carries the weight of centuries past. With a private driver and expert guides leading the way, this journey invites you to uncover Ireland’s soul, from its grand castles to its intimate coastal villages, all while indulging in the finest experiences the Emerald Isle has to offer.
7 days tailor-made from £4,525 per person View trip
Explore Ancient Scotland: LGBTQ+ Friendly Heritage Tour
Tailor-made HolidayEmbark on a journey through Scotland, a land where rugged landscapes and ancient history converge to create a truly magical experience. From the enchanting Highlands to the windswept Orkney Isles, this itinerary takes you through vibrant cities, dramatic coastlines, and prehistoric wonders. Immerse yourself in Scotland’s rich culture, savour its timeless traditions, and let its breathtaking beauty capture your heart.
8 days tailor-made from £7,950 per person View trip
Luxury England Tour: London, Windsor & the Cotswolds
Tailor-made HolidayThis isn't just another trip to England - it's your chance to experience the country like royalty, with all the perks and none of the protocol or ribbon-cutting. Start in London, where you'll skip the tourist crowds and dive straight into the good stuff. Take a private tour of Kensington Palace (yes, where Diana lived), then settle in for afternoon tea in the palace gardens.
10 days tailor-made from £16,775 per person View trip
Luxury Rail Journey: London, York & the Royal Scotsman
Tailor-made HolidayThis journey is built around one of the most luxurious rail experiences in the world: the Belmond Royal Scotsman. Before boarding, you’ll spend time in London and York, with private touring that gives you a proper sense of England’s history, architecture and character. From there, continue north to Edinburgh, where the pace changes completely. The Royal Scotsman is the centrepiece.
10 days tailor-made from £10,220 per person View trip
Undiscovered Japan Tour – Shirakawa-go, Tottori & Noto
Tailor-made HolidayMost first trips to Japan follow the Tokyo, Kyoto and Osaka route. This one deliberately goes elsewhere. Over ten days, you travel through western and central Japan, beginning and ending in Osaka but spending most of the trip in smaller cities, mountain towns and coastal regions. Kanazawa introduces you to samurai history and local craft before the route continues through the Noto Peninsula and into Shirakawa-go, where steep-roofed gassho-zukuri farmhouses sit among the mountains.
10 days tailor-made from £7,650 per person View trip
Timeless Puerto Rico: Culture, Coastlines and Canopies
Tailor-made HolidayStep into the heart of the Caribbean with this extraordinary nine-day journey through Puerto Rico, where every moment is designed to inspire. From the cobblestone streets of Old San Juan to the tranquil shores of Vieques, this trip blends history, natural beauty, and a vibrant culture into a seamless celebration of life and exploration.
9 days tailor-made from £5,950 per person View trip
Passion in Paradise: St Lucia and Grenada Honeymoon
Tailor-made HolidayNine days across St Lucia's volcanic south and Grenada's spice-scented coast, from the Pitons to the nutmeg groves. St Lucia opens the trip with four nights built around the Pitons, the pair of volcanic spires that anchor the island's southwest coast.
8 days tailor-made from £8,200 per person View trip
Ultimate Luxury: St Lucia, North to South
Tailor-made HolidayEight days across the volcanic peaks, quiet rainforest, and cacao hills of St Lucia's south and north. The south holds the island's signature view: the twin Pitons rising directly from the sea at Soufriere, with a working volcano and a rainforest pressing in behind them.
8 days tailor-made from £5,740 per person View tripFrequently asked questions
What does Out Of Office do?
Out Of Office is a luxury LGBTQ+ travel company specialising in tailor-made holidays and extraordinary journeys around the world. We create bespoke luxury holidays, 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 personalised 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 travelling as an LGBTQ+ person or couple, from local laws and customs to finding genuinely welcoming hotels and experiences.
We welcome every traveller, 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, personalised service and discretion.
Do you create tailor-made LGBTQ+ holidays?
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 personalised 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+ travellers 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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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 travelling 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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