Inspiration
Transgender Vacations
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.
We recommend
Trans travelers deserve the same kind of trip everyone else does. The villa with the view, the overwater bungalow, the boutique hotel with the perfect terrace for coffee at sunrise. That’s where we start, and it’s where most of the planning sits.
The destinations our trans clients book most often are also some of the most rewarding places we sell into anywhere: the Greek Islands, where Mykonos in particular has been a touchstone for LGBTQ+ travel for decades and trans visibility in the bars, beaches, and restaurants is part of the fabric of the island.
Gran Canaria, with its long-established LGBTQ+ scene in Maspalomas and Playa del Inglés, year-round sunshine, and resorts that have been hosting LGBTQ+ guests for generations. Sitges and Barcelona, where Spain’s strong legal framework and trans-affirming culture make for some of the most relaxed luxury beach trips in Europe. Thailand, where marriage equality passed in January 2025 and trans visibility has been a part of public life for far longer than the legal change. Mexico’s Puerto Vallarta and Mexico City. Cape Town. Bora Bora and the wider South Pacific, where the Polynesian concept of māhū has meant trans and gender-nonconforming people have held respected cultural roles for centuries.
Trans travel has considerations gay and lesbian travel doesn’t always share. Passport gender markers that may not match your presentation, security screening, hormone supplies through customs, hotel check-in protocols. None of this is insurmountable, but it’s the kind of thing a generalist operator won’t think to ask about, and we will. When you inquire, we’ll talk through the destinations you’re drawn to, flag anything practical worth knowing, and brief the hotels in advance where it adds value.
If there are countries we’d suggest approaching with more care, we’ll tell you, and we’ll explain why. Honesty about what trips look like on the ground is part of the service.
A decade of running LGBTQ+ luxury travel means we’ve handled most things you might want to ask about, and a few you might not have thought of yet. The goal is the same as any trip we plan: a holiday that’s properly considered, beautifully delivered, and built entirely around how you actually want to travel. Get in touch and we’ll start planning.
Suggested Transgender Vacation Trips
Trans Honeymoons and Special Occasions
Some of the most rewarding trips we plan are the ones built around a moment that matters. A wedding, an anniversary, a milestone birthday, a long-postponed honeymoon. For trans clients, those occasions often carry an additional layer of meaning, and the trips we put together reflect that.
Honeymoons are where we see the strongest demand. Overwater villas in the Maldives and Bora Bora, where private-island settings mean the resort is effectively your own world for the week. Greek island combinations that pair Mykonos with the quieter beaches of Paros or Milos. Italian itineraries that move between Lake Como, the Amalfi Coast, and Capri. South African trips that combine Cape Town and the Winelands with a few nights on safari at one of the private reserves around Kruger. We’ve planned honeymoons across most of these and know which suites, villa categories, and dining setups work best for couples wanting privacy alongside genuine luxury.
Milestone birthdays and anniversaries often take a different shape. A private villa in Tuscany or Provence with a group of close friends. A booked-out riad in Marrakech. A chartered yacht through the Greek islands or the Croatian coast. These are the trips where having a specialist matters most, because the details (who sits where at dinner, which property has the right number of bedrooms, which destinations make sense for the time of year) are what turns a special occasion into one that’s remembered properly.
For weddings themselves, we work with planners and venues across destinations where same-sex marriage is legally recognized and where the local supplier network has experience hosting LGBTQ+ ceremonies. South Africa, Spain, Portugal, Mexico, and Italy all work well in different ways, and we’ll talk you through which fits the kind of day you’re imagining.
Santorini Trans Travel
Related reading
Exploring LGBTQ+ Art in Italy: From the Romans to the Renaissance
Standing before Donatello’s bronze David in Florence, there is time to notice what photographs rarely capture: the delicacy of his stance, the curve of his hip, the contrast between his slight frame and Goliath’s sword. For LGBTQ+ travelers, exploring Italy’s art can bring another dimension to these encounters, opening conversations about male beauty, same-sex desire and the lives of the artists behind the masterpieces.
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A Cultural Tour of Ireland: Art, Literature & LGBTQ+ Heritage
Ireland has long been associated with romance. The Emerald Isle has produced a disproportionately high number of artists and writers. During times of national trauma, Ireland's artists have rallied, producing classic works. In recent years, Ireland has emerged from its turbulent history as a rich and socially liberal country. Ireland’s literary and artistic legacy is shaped by LGBTQ+ voices, music, and timeless storytelling.
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Barcelona & Sitges in 7 Days: A Luxury Gay-Friendly Spain Journey
Tailor-made VacationImmerse yourself in the vibrant LGBTQ+ culture of Spain with a journey through two of the continent's most welcoming destinations: Barcelona and Sitges. Start in Barcelona, a city brimming with both historic character and modern energy. Discover Antoni Gaudí’s iconic architecture, including Park Güell, and explore the narrow streets of the Gothic Quarter, where medieval buildings sit alongside stylish boutiques and busy cafés.
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Walt Disney World Florida
Tailor-made VacationBring your childhood memories to life and step into the magic at Walt Disney World Resort Florida. Whether you're looking for a Disney family vacation or you're a big kid looking to fulfill your childhood dreams, we can create your dream Disney getaway. With a great selection of hotels on offer and a Disney park that will grant every wish, your vacation will be one you will never forget.
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Greek Island Hopping: Milos, Paros and Mykonos
Tailor-made VacationMilos, Paros, and Mykonos make for a brilliant Greek island trilogy. This route takes you from under-the-radar beaches to charming village life, finishing with Mykonos's signature glamour. Begin in Milos, the Cyclades' best-kept secret (though the word is getting out). With over 70 beaches—many only accessible by boat—this volcanic island delivers dramatic coastlines, lunar landscapes, and crystal-clear waters without the crowds you'll find elsewhere.
8 days tailor-made from $1,490 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.