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
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 travelers, 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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Gay Family Travel: The Essential Guide to Travel Documentation for LGBTQ+ Families
Traveling 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 recognized 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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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 Ultimate Guide to Packing for a Trip with Children
Traveling 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 traveling 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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Caribbean LGBTQ+ Rights: Which Islands Recognize Same-Sex Marriage?
The Caribbean is a dream vacation 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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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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Barbados vs Bequia: Which Island Should You Visit?
When it comes to choosing between Barbados and Bequia for your Caribbean getaway, it’s a bit like comparing champagne to a fine rum—both are exquisite, but they have distinctive charms. What’s more, both can be enjoyed alongside each other - if you’re the type of person who likes to break with convention. We'll also unravel the mystery of how you get to Bequia and the best ways to combine it with Barbados.
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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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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+ travelers, 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 Gay Family Vacation Destinations Around The World
From beautiful beach destinations to family-friendly city escapes, there are so many amazing places for gay families to vacation. Whether you’re looking for a fun weekend getaway or a longer staycation, this list of our top spots is sure to have something special for your family. Be sure to check out LGBTQ+ family vacations for more information on why Out Of Office is such a great choice for LGBTQ+ families.
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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+ travelers? 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 gay resorts for singles
Gay solo travel opens up a world of possibilities for LGBTQ+ individuals. It allows you to explore new destinations, connect with like-minded people, and embark on exciting adventures. Unlike traveling with companions, solo travel provides the freedom to go wherever and whenever you desire, making it an ideal choice for those seeking cultural experiences, relaxation, thrilling activities, or a mix of all these options.
ReadTrips through Caribbean
Ultimate Luxury Mexico: Punta Mita, Los Cabos & Riviera Maya
Tailor-made VacationThree coastlines, one itinerary, entirely shaped around you. Move between three of Mexico's most distinct coastal regions, each with its own rhythm. From the private peninsula of Punta Mita to the dramatic cliffs of Los Cabos and the reef-lined shore of the Riviera Maya, the trip is built entirely around the version of Mexico you want to see.
9 days tailor-made from $8,920 per person View trip
Classic Caribbean: Aruba and Curacao
Tailor-made VacationRenowned for offering the quintessential Caribbean experience – white sands, swaying palm trees, and crystal-clear waters – Classic Caribbean: Aruba and Curacao forms one of our favorite twin-center vacations. 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 $4,445 per person View trip
Miami & Caribbean Cruise
Tailor-made VacationExperience Miami's welcoming energy, Caribbean sailing, and island time in the Bahamas, all in one luxury trip. This nine-day trip opens in Miami, a city whose LGBTQ+ history runs deep along South Beach and Ocean Drive, where Art Deco facades and an easy, sun-soaked pace set the tone for the days ahead.
9 days tailor-made from $7,360 per person View tripWhere to stay in Caribbean
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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.