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 25–36 of 54
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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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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Plan Your Gay Honeymoon in Puerto Rico
Puerto Rico occupies a singular space in the Caribbean imagination. It's technically stateside, which means no passport shuffling for American travellers, yet the moment you land in San Juan, the air thick with salt and the faint pulse of reggaetón drifting from somewhere unseen, you're unmistakably elsewhere.
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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.
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Tropical Destinations Where Gay Couples Can Legally Marry
Thailand became the first Southeast Asian country to legalize same-sex marriage in January 2025, joining a growing list of tropical destinations where gay couples can exchange vows legally. With 38 countries now recognizing marriage equality, LGBTQ+ couples have more stunning tropical options than ever before for their dream destination wedding.
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Gay Family Travel: The Essential Guide to Travel Documentation for LGBTQ+ Families
Travelling as an LGBTQ+ family is a beautiful way to explore the world together, but it often comes with unique challenges, especially when it comes to documentation. Preparing thoroughly is key to ensuring smooth journeys, particularly if you’re heading to destinations where LGBTQ+ rights are not recognised or protected. Here’s everything you need to know about travel documentation, passports, and what to consider as an LGBTQ+ family.
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Caribbean LGBTQ+ Rights: Which Islands Recognise Same-Sex Marriage?
The Caribbean is a dream holiday spot but it's something of a minefield if you're LGBTQ+. Gay rights vary considerably across the Caribbean, ranging from super gay-friendly islands like Aruba to far less welcoming islands, such as Jamaica. In this article, we'll focus on the varied legal landscape in the Caribbean islands. Gay marriage is legal in some of the islands, so you can even plan a gay wedding or honeymoon in the Caribbean.
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Gay Family Travel: The Ultimate Guide to Packing for a Trip with Children
Travelling with children is a joyous yet intricate task, and for gay families, it’s also a powerful celebration of love and inclusivity. Whether you are travelling with a newborn—perhaps welcoming a baby born via surrogacy—toddlers, or small children, a well-prepared packing list is your gateway to stress-free adventures. Here’s a comprehensive guide to what to pack, broken down by age group, while ensuring everyone’s comfort and entertainment.
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Is St. Barths Gay-Friendly?
St. Barths, or Saint Barthélemy, is one of the most exclusive and glamorous islands in the Caribbean, renowned for its luxurious resorts, pristine beaches, and upwardly mobile social scene. For LGBTQ+ travellers, St. Barths offers an incredibly welcoming atmosphere, with its French influence contributing to a laid-back and inclusive culture.
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The Best Luxury Honeymoon Destinations Around the World
Are you dreaming of a honeymoon that exudes luxury and extravagance? Look no further, as we take you on a journey to explore the best luxury honeymoon destinations around the world. From breathtaking villas nestled in the Maldives to exclusive resorts in the Caribbean, these destinations promise an unforgettable experience for couples seeking opulence and romance.
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Is Anguilla Gay Friendly?
Anguilla, a tranquil gem in the Caribbean, is celebrated for its pristine beaches, luxury resorts, and relaxed atmosphere. But how welcoming is it for LGBTQ+ travellers? Let’s explore what makes Anguilla a promising destination for gay visitors, while also considering its cultural nuances and legal environment.
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The Best Things to do in Mexico
Mexico offers an endless range of activities and attractions – from discovering the secrets of ancient civilizations to experiencing the hustle and bustle of a modern metropolis. For those who love exploring, there are a plethora of awe-inspiring ancient ruins, breathtaking nature reserves, and stunning beaches to explore. If you're a foodie, Mexico has a huge variety of delicious local dishes waiting to be sampled.
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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
Caribbean Jewels: Barbados and Antigua
Tailor-made HolidayPicture a journey where turquoise waters, golden beaches, and vibrant cultures create the perfect backdrop for an unforgettable adventure. This twin-island itinerary invites you to experience the welcoming charm of the Caribbean, where everyone is free to celebrate love and individuality. Begin in Antigua, where the historic Nelson’s Dockyard and breathtaking views from Shirley Heights set the stage for your island adventure.
11 days tailor-made from £4,445 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.
One named specialist, first enquiry to homecoming. No call centre, and nothing is charged until you decide to book.