Posted in Editorials
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.
Here at Out Of Office, we truly understand the world you live in, and the world you want to explore. Our attention to detail, exceptional service and deep understanding of both luxury travel and LGBTQ+ travel make us a fantastic choice for those looking for a travel experience where exclusivity meets inclusivity.
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 enquire, 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.
Trans luxury travel is in a stronger place than it’s ever been. More countries with full legal protections, more hotels with trained staff and informed reservations teams, more destinations where the welcome is built in. The trips our trans clients...
Tailor-made Vacation
Experience the perfect mix of history and relaxation on this indulgent luxury island-hopping adventure through Athens, Mykonos, and Santorini on one of our most popular trips. Over eight days, this deluxe itinerary allows you to uncover ancient Greek ruins, explore...
Tailor-made Vacation
Discover the passionate world of Mexico’s most famous artist on this immersive journey through Frida Kahlo’s life, loves, and revolutionary spirit. From her childhood home in Coyoacán to the streets where she found inspiration, this itinerary celebrates not only her...
Tailor-made Vacation
At Out Of Office, French Polynesia is one of our most popular destinations, and it isn’t hard to see why – you’ll find a vast collection of beautiful beaches, unspoiled jungles, and world-class resorts here. The LGBTQ+ friendly territory comprises...
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.
Tailor-made Vacation
Rio’s Carnival is the largest annual gathering on the planet, and one of the most LGBTQ+-friendly parties in the world. The blocos are out, the Sambadrome runs through the night, and the city’s gay calendar moves in parallel from Friday...
Tailor-made Vacation
The French Riviera blends coastline, culture, and an upwardly mobile social scene that feels unmistakably European, moving from the relaxed of Nice to the wealth of Monaco and the beach clubs of Saint-Tropez. This itinerary is designed to flow naturally,...
Tailor-made Vacation
This two-island escape brings together two of Greece’s most captivating Cycladic islands, Mykonos and Paros – each offering something beautifully different in one of the world’s most LGBTQ+-friendly nations. Start in Mykonos, the icon of Greek island glamor and luxury....
Tailor-made Vacation
Journey through the filming locations of the now legendary 2008 musical, combining cinematic nostalgia with luxury Greek island experiences in LGBTQ+-popular destinations. The film was primarily shot on the Greek islands of Skopelos and Skiathos in the Sporades archipelago, with...
Tailor-made Vacation
This luxurious ten-day escape offers LGBTQ+-friendly experiences in two of the most welcoming cities in the United States. Designed for those who appreciate both the finer things in life and a rich, welcoming community, this itinerary promises an unforgettable exploration...
Tailor-made Vacation
Spend 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...
Tailor-made Vacation
Imagine 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 –...
Group Trip
Brand new for 2024, the Luxury Tuscan Summer tour is an opportunity to be immersed in the flavours of Tuscany, exploring epic sights and dining on culinary delights. Known for its landscapes, storied history, legacy of artistic innovation, and place...
Tailor-made Vacation
While geographically compact, Israel punches far above its weight in cultural significance and diversity of experiences. This ancient land where the three major monotheistic faiths intersect is a tapestry of sacred sites, storied cities, and contrasting landscapes that will enlighten...
Group Trip Departs: • 4th September 2026
Stay in a 600-year old castle in Tuscany, perched on a hillside overlooking vineyards and a historic village. You’ll be exploring one of the most beautiful parts of Italy with 30 gay travelers. Sun yourself by the private pool, explore...
Tailor-made Vacation
Puerto Vallarta is one of the most popular vacation spots for US travelers. Overlooking Banderas Bay and surrounded by the Sierra Madre, it’s an impeccable beach destination. You’ll find a huge gay scene in Zona Romantica – it’s Latin America’s...
Tailor-made Vacation
Riviera Maya is the place to be on Mexico’s Caribbean coast. Cancun is the most tourist-friendly part of the country. It’s packed with luxury resorts. The sprawling Zona Hotelera is a district that’s comprised – as the name suggests –...
Group Trip
Colombia was ravaged by the drug wars in recent years, as dedicated Netflix viewers will know all too well. Signor Escobar is long dead and Colombia has emerged as one of the hottest tourist destinations in Latin America. Quite an...
Tailor-made Vacation
Get ready for an unforgettable experience at Sitges Pride, one of Europe’s premier Pride events in one of Europe’s most gay-friendly destinations. Taking place in June each year, this vibrant celebration always delivers an extravaganza of pool parties, boat excursions,...
Tailor-made Vacation
Immerse 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...
Tailor-made Vacation
Bring 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...
Group Trip
Embark on an enchanting journey through the heart of Europe, where each city along the Rhine River is a hidden gem waiting to be uncovered during your unforgettable gay cruise adventure. This all-queer full cruise charter aboard the Amadeus Queen...
Tailor-made Vacation
Milos, 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)....
Group Trip
Starting in Sydney, this trip is an amazingly diverse gay adventure! From Urulu / Ayers Rock to Sydney Opera house, this luxury group trip is filled with the iconic sights of Australia. Beginning in Sydney, you will fly to Uluru...
We want to ensure you have the best experience with us so we’ll keep working on your itinerary until perfect. You will have your own personal dedicated member of our team who will help build a trip that is bespoke to you.
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