Caribbean
Caribbean Travel Guides
Written by the specialists who plan our trips to Caribbean: where to go, when, and what is worth knowing before you book.
All Caribbean Travel Guides
Showing 13–24 of 54
The World’s Most Exclusive Private Islands for LGBTQ+ Travellers
There is a category of travel that exists beyond the five-star hotel, beyond the overwater villa, beyond the private pool. It is the private island, and it operates on a different logic entirely. No other guests to navigate. No public beach. No shared anything. Just the island, the water, and complete, uncompromising seclusion. Every island on this list welcomes LGBTQ+ travellers, and most have hosted countless same-sex couples and groups over the years.
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Best Gay-Friendly Beaches in Cabo
The story of Cabo San Lucas for LGBTQ+ travellers is refreshingly straightforward. There's no distinct scene but it’s very gay-friendly. Cabo San Lucas sits at the southern tip of the Baja California peninsula, where the Pacific Ocean and the Sea of Cortez collide. The iconic El Arco (the Arch) rises 300 feet from the water, creating a dramatic focal point.
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Plan Your Gay Honeymoon in Turks and Caicos
Forty islands. Water the colour of a swimming pool that goes on forever. Some of the most exceptional resorts in the Caribbean. Turks and Caicos is a highly appealing honeymoon proposition. Turks and Caicos has quietly built a reputation as one of the most welcoming destinations in the Caribbean, and the luxury end of the market here is inclusive.
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Best Gay Beaches in Puerto Vallarta
Puerto Vallarta is Mexico's gay capital, and unlike many LGBTQ+ beach destinations, this place doesn't just tolerate gay travellers. It’s largely built around their needs and interests. The beaches that matter are concentrated in and around Zona Romantica, the Gayborhood where LGBTQ+ hotels and bars await. Playa Los Muertos Playa Los Muertos is the gay beach of Puerto Vallarta and is one of the most famous beaches in Mexico and beyond.
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The Shortest Runways in the Caribbean
There is a certain moment, just before landing, when you realize this is not a typical arrival. The aircraft drops lower than expected, the runway appears almost suddenly, and for a brief second it feels as though you are landing somewhere that should not quite be possible.
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Cabo vs Riviera Maya: Which is Better?
Mexico's coastlines is home to some of the world's most spectacular luxury holiday spots, but two regions consistently stand out for Out Of Office travellers: the desert meets-ocean beauty of Los Cabos and the tropical paradise of Riviera Maya. These coastal paradises represent the pinnacle of Mexican luxury travel.
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Plan Your Gay Honeymoon in St Barths
There is a particular kind of honeymoon that St Barths does better than almost anywhere else in the Caribbean. Not the all-inclusive resort honeymoon, not the activity-packed island-hopping honeymoon, but the one built around two people, a terrace with a view, and the unhurried pleasure of having nowhere specific to be.
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How Liz Taylor Turned Puerto Vallarta into Mexico’s Gay Paradise
Long before Puerto Vallarta became Latin America's premier LGBTQ+ party destination, this once-sleepy fishing village along Mexico's Pacific coast was transformed by a scandalous Hollywood love affair that captured worldwide attention in the 1960s.
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The Celebrity Caribbean: Why the Most Discerning Travellers Choose Turks and Caicos
Turks and Caicos has become a magnet for A-listers seeking privacy and luxury, and it's not hard to see why. The beaches are world-class. Grace Bay is long, wide, and protected by a barrier reef, which keeps the water calm, clear, and consistently swimmable. No seaweed issues, no rough surf, no trade-offs. The hotels operate at a global standard, not a Caribbean one.
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The Best Gay Hotels in Puerto Vallarta
Puerto Vallarta is one of the best luxury destination in Latin America, as well as being home to the region’s largest gayborhood. It’s home to a stunning AAA Five Diamond resort, Hotel Mousai. It’s also home to a growing luxury LGBTQ+ hotel scene. The Tryst Puerto Vallarta opened in fall 2024, becoming the world's first luxury gay hotel brand.
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Gay Sailing Charters in the Caribbean: Luxury Yacht Experiences
The Caribbean offers more straightforward sailing conditions for LGBTQ+ travellers than most ocean destinations. Island nations here range from actively welcoming (St Barths, US Virgin Islands) to legally hostile (Jamaica), but the luxury yacht charter infrastructure operates with professional neutrality regardless of local attitudes. Most crews working the high-end charter circuit come from Europe, Australia, or the US, bringing service standards that don't vary based on passenger orientation.
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Plan Your Gay Honeymoon in Puerto Vallarta
Puerto Vallarta is one of the most popular LGBTQ+ holiday spots on the planet. PV is located on the coast between the Sierra Madre mountains and Banderas Bay. It’s been welcoming same-sex couples for decades, creating an infrastructure of gay-owned businesses, inclusive resorts, and romantic experiences. It’s also a great destination for a honeymoon. It's packed with luxury hotels, buzzing gay nightlife, romantic beaches and concierge services for luxury travellers.
ReadTrips through Caribbean
Ultimate Luxury Mexico: Punta Mita, Los Cabos & Riviera Maya
Tailor-made HolidayThis extraordinary journey combines the vibrant essence of Mexico's most colourful cities with the breathtaking beauty of its coastal landscapes. Prepare to immerse yourself in the unique blend of cultural marvels and natural wonders that Mexico has to offer, all while basking in unparalleled luxury and comfort.
9 days tailor-made from £6,725 per person View trip
Classic Caribbean: Aruba and Curacao
Tailor-made HolidayRenowned for offering the classic Caribbean experience – white sands, swaying palm trees, and crystal-clear waters – Classic Caribbean: Aruba and Curacao forms one of our favourite twin-centre holidays. These islands invite you to immerse yourself in natural beauty while indulging in world-class hospitality, all set against the stunning backdrop of the Caribbean Sea. Aruba and Curacao are incredibly LGBTQ+ friendly, making them standout destinations for inclusive travel.
7 days tailor-made from £3,350 per person View trip
Miami & Caribbean Cruise
Tailor-made HolidayEscape on an alluring journey to Miami, Costa Maya, and the Bahamas on this luxury Miami and Caribbean cruise itinerary. Experience Miami's exhilarating energy before retreating to the Caribbean Sea's tropical serenity on this luxurious tour. You'll begin your indulgent Miami and Caribbean holiday at Nobu Hotel Miami Beach, a sophisticated beachfront urban oasis ideally located in the heart of Miami Beach.
9 days tailor-made from £5,550 per person View tripWhere to stay in Caribbean
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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.
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