Inspiration
Gay Retreats USA
Tailor-made, always
Every trip built from scratch around your dates, pace and preferences.
Your own specialist
One named person and a 24-hour number while you travel.
Hundreds of five-star reviews
Rated Excellent on Trustpilot across ten years of LGBTQ+ luxury travel.
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
Related reading
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.
Read
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
Related reading
The best rooftop bars in New York
Where better to enjoy a rooftop cocktail than in the city that never sleeps, New York. Here's the OutOfOffice.com run down of our tried and tested best rooftop bars in New York. Salon De Ning New Yorkers aplenty visit Salon de Ning so you know it must be on point.
Read
Best Gay Honeymoon Destinations 2027 & 2028
At Out Of Office, we specialize in creating exceptional gay honeymoons for couples who want more than just a beautiful destination. Our LGBTQ+ honeymoon specialists have planned thousands of same-sex honeymoons worldwide, giving us unrivaled insight into where offers the perfect balance of romance, privacy, luxury, and genuine inclusivity. With 2027 honeymoon bookings well underway, couples are planning further ahead than ever.
ReadThe best gay retreat hotels in the USA
More cultural trip ideas worldwide
Showing 181–192 of 318
Explore Ancient Greece
Tailor-made VacationTake a step into Ancient Greece on this eight-day luxury Greece history tour. You'll travel from Athens to Delos and beyond, visiting archaeological sites, captivating museums, and ancient relics alike. Our tailor-made itinerary provides a fascinating glimpse into this ancient civilization alongside indulgent hotels, each sporting a classical, heritage feel. In Athens, you can explore the famous sightseeing spots alongside an expert historian guide.
8 days tailor-made from $4,495 per person View trip
Ultimate Luxury Greece: Athens, Mykonos & Santorini
Tailor-made VacationThis is the most luxurious way to experience Greece, combining Athens, the Athens Riviera, Mykonos, and Santorini with some of the country’s best hotels, private guides, yacht transfers, and seamless logistics. You’ll stay at Hotel Grande Bretagne in Athens, Four Seasons Astir Palace on the Riviera, Bill & Coo in Mykonos and Canaves Oia in Santorini.
10 days tailor-made from $13,035 per person View trip
Classic Italy by Train
Tailor-made VacationTwo weeks, four cities, and not a single flight between them. Italy's high-speed rail network turns city-hopping into the easiest part of the trip, Venice to Florence in a little over two hours, Florence to Rome in ninety minutes, each transfer short enough that you spend your time seeing the country rather than getting to it.
14 days tailor-made from $6,385 per person View trip
Luxury Italy Tour: Lake Como, Tuscany, & Amalfi
Tailor-made VacationThis fully customizable itinerary moves through four of Italy's most distinctive regions, Lake Como's lakeside villas, Tuscany's vineyard hills, Rome's history, and the Amalfi Coast's cliffside towns, each with its own character. Expect regional wine, Michelin-starred dining, and produce sourced from wherever you happen to be standing, along with stays in a palazzo, a private villa, and two of the country's most established hotels.
9 days tailor-made from $11,950 per person View trip
Luxury
New Zealand Gay Travel: Auckland, Rotorua & Queenstown
Tailor-made VacationEleven days covering both islands, moving at a pace that actually lets the country land. New Zealand rewards people who don't rush it. It's one of the furthest-flung destinations on earth for European travelers, and around a fourteen-hour flight for American travelers.
11 days tailor-made from $6,120 per person View trip
Luxury
Luxury Peru: Lima, Cusco & Machu Picchu with Belmond
Tailor-made VacationPeru is one of the great travel destinations, and this journey covers it at the level it deserves. Lima is one of South America's finest food cities, with Central and Maido consistently ranking among the best restaurants in the world. Cusco is the former capital of the Inca Empire, its colonial churches and palaces built directly onto Inca stone foundations that have outlasted everything placed on top of them.
9 days tailor-made from $9,310 per person View trip
Sri Lanka in Five Days: Rock Fortress to Tea Hills to Coast
Tailor-made VacationThe road from Sigiriya's rock fortress to the tea hills of Nuwara Eliya changes character almost by the hour, and this trip is built to let you feel every shift. This itinerary moves efficiently through the island's essentials: the ancient rock fortress of Sigiriya, the sacred Temple of the Tooth in Kandy, the cool hills of Nuwara Eliya's tea country, and a final stretch of coastline at Mirissa, without the trip ever feeling rushed.
5 days tailor-made from $2,595 per person View trip
Luxury Puerto Rico
Tailor-made VacationWith its world-renowned stretches of white-sand beach, rich cultural heritage, and a range of luxury accommodations, Puerto Rico is one of the Caribbean’s best destinations for a truly luxurious, LGBTQ+-friendly island getaway. Our luxury Puerto Rico itinerary is meticulously crafted to showcase the finest aspects of this enchanting destination, and is one of our most popular escapes with our clients.
9 days tailor-made from $4,230 per person View trip
LGBTQ+ Puerto Rico Culinary Tour: San Juan, Ponce
Tailor-made VacationPuerto Rico's food carries three distinct histories at once: Taino root vegetables and cooking techniques, Spanish stews and sofrito, and West African ingredients brought through the slave trade, most visibly in dishes built on plantain and salted cod. That layering is still legible on the plate. Mofongo, made from mashed green plantain, and arroz con gandules, rice cooked with pigeon peas, both trace directly back to it.
7 days tailor-made from $4,655 per person View trip
Ultimate Luxury: The Seychelles
Tailor-made VacationThe nine-day Ultimate Luxury: The Seychelles itinerary is the final word when it comes to unbridled luxury on the Indian Ocean’s most exclusive island archipelago. Throughout your trip, you’ll not only get to spend time relaxing on some of the world’s most picturesque beaches but also unwind in the sumptuous luxury of three five-star resorts.
9 days tailor-made from $5,520 per person View trip
Ultimate Luxury: United Kingdom
Tailor-made VacationDiscover the wonder of the United Kingdom on this nine-day Ultimate Luxury itinerary. You’ll be staying in the best hotels and eating in the finest restaurants as you explore the cosmopolitan sprawl of London, the cultural majesty of Edinburgh, and the bucolic paradise of the British countryside. Focusing on three of the country’s most exclusive luxury properties, this customizable itinerary promises a dream United Kingdom vacation with bespoke add-ons and perks.
9 days tailor-made from $12,500 per person View trip
The Best Of Rajasthan
Tailor-made VacationDiscover Rajasthan, India's quintessential jewel. This vast region, India's largest, is a treasure trove of medieval forts, palaces, and an abundance of national parks, offering a peek into the country's rich tapestry of history and culture. From the multicolored craft markets to the pink hues of Jaipur, Rajasthan promises an explosion of colors and experiences unmatched anywhere else in India.
15 days tailor-made from $3,500 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.
Stellar service. Stellar products. Stellar people and it gets so much better when you pick up the phone and call.
Anthony S.
Super client centred service. From first contact I have had warm, efficient, friendly and flexible service.
John
I’m confident in giving Out Of Office a 5-star review! They are one of the leaders in this space without a doubt.
Tiberiu
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.
We donate to Rainbow Railroad with every booking
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.
One named specialist, first inquiry to homecoming. No call center, and nothing is charged until you decide to book.