Tailor-made trips for 2027 & 2028
Gay Travel in North America
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.
Luxury gay vacations in North America
North America is a continent of scale, diversity, and unforgettable contrasts, where iconic cities, vast natural beauty, and world-class luxury come together effortlessly. For LGBTQ+ travelers, it is one of the most varied regions in the world, offering everything from vibrant cultural capitals to relaxed island escapes. With decades of experience crafting bespoke journeys across the continent, Out Of Office designs North American itineraries that are seamless, celebratory, and entirely tailored to you.
The United States delivers classic bucket-list experiences at every turn. Take to the open road on a legendary Route 66 adventure, immerse yourself in the energy of New York City, or explore the creativity and glamour of Los Angeles. From Broadway and world-class museums to beaches, deserts, and national parks, the USA offers limitless ways to travel, elevated with insider access, luxury stays, and expert planning.
For a true tropical escape without leaving the US, Hawaii is unrivalled. Dramatic volcanic landscapes, lush rainforests, and pristine beaches create a setting that feels far removed from everyday life. Spend your days unwinding on white-sand shores, hiking through extraordinary scenery, or enjoying ultra-luxury resorts designed for privacy, romance, and relaxation.
Further north, Canada combines sophisticated cities with breathtaking wilderness. Discover the cultural energy of Toronto and Vancouver, ski the slopes of Whistler, or experience the natural drama of Niagara Falls. Canada is ideal for travelers seeking cosmopolitan flair alongside unforgettable outdoor adventure.
In the Caribbean, Puerto Rico offers a vibrant blend of culture, history, beaches, and nightlife, all with the ease of US travel. From the colorful streets of Old San Juan to luxury coastal resorts, it is a destination that balances relaxation with rich local character.
Whether you are planning a city-led escape, a once-in-a-lifetime road trip, a beach-focused fly-and-flop holiday, or a multi-country journey showcasing the best of the continent, Out Of Office curates North American travel with precision, confidence, and care. Every detail is handled so you can focus on experiencing each destination exactly as you want to.
Our Most Popular Trips
Our itineraries are here to inspire you. Everything we do is tailor-made so our team of luxury travel experts will customise an itinerary for you.
Boston and Provincetown
Tailor-made HolidayEmbark on a captivating Massachusetts adventure, starting in the historic city of Boston. Spend a couple of days exploring Boston's rich history, particularly its pivotal role in the American Revolution. Walk the famous Freedom Trail, visit the historic Faneuil Hall Marketplace, and stroll along the Boston Harbor. After soaking in Boston's historical ambiance, head to Provincetown at the tip of Cape Cod.
10 days tailor-made from £4,500 per person View trip
Whales, Bears and Vancouver Island
Tailor-made HolidayEmbark on an unforgettable journey through the pristine landscapes and captivating culture of western Canada with this meticulously curated itinerary. Over the course of nine days, travellers will immerse themselves in the diverse ecosystems and vibrant communities of Vancouver Island and the mainland. The adventure begins in Victoria, the provincial capital, where travellers will have the opportunity to explore the charming streets and scenic waterfront of British Columbia's capital city.
9 days tailor-made from £2,395 per person View trip
Miami and Puerto Rico
Tailor-made HolidayExperience the epitome of luxury with our exclusive twin-centre itinerary, featuring two of the USA's premier destinations: Miami and Puerto Rico. These vibrant locales offer a captivating blend of dazzling splendour and stunning coastal landscapes, making them perfect for discerning travellers seeking an unforgettable getaway. Miami, renowned as the epitome of colourful luxury along the Caribbean coast, beckons with its dazzling array of luxury properties and vibrant cultural scene.
9 days tailor-made from £2,605 per person View tripOur Most Popular North American Destinations
Featured Luxury Hotels in North America
Frequently asked questions
About North America
Where should I go in North America?
Our North America itineraries most often feature the USA, Costa Rica and Canada, followed by Bermuda.
Can my trip to North America be tailor-made?
Yes. Everything we plan is tailor-made. Our suggested North America itineraries are starting points: your specialist shapes the countries, the route, the hotels, the pace and the length around your dates and preferences. As a guide, our suggested North America itineraries run from 7 to 17 days.
Which luxury hotels do you recommend in North America?
Our specialists' current picks across North America include The Little Nell (USA), Hamilton Princess and Beach Club (Bermuda) and Hacienda AltaGracia, Auberge Collection (Costa Rica), each handpicked for how it welcomes every guest.
Where should I honeymoon in North America?
Our 24 North America honeymoon itineraries most often feature the USA, Canada and Costa Rica, each tailored around the two of you.
Do you run group trips in North America?
Yes. Our next small-group departure in North America is Gay Group Trip: Costa Rica Adventure, leaving on 22 January 2027. Tailor-made trips run year-round.
Travelling with Out Of Office
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.
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 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.
One named specialist, first enquiry to homecoming. No call centre, and nothing is charged until you decide to book.