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 1–12 of 54
Is the Caribbean Gay Friendly?
There's so much to see and do in the Caribbean. Explore the colonial charm of Old San Juan in Puerto Rico, with its cobblestone streets, pastel-colored buildings, and historic forts like Castillo San Felipe del Morro. In Aruba, relax on Eagle Beach, famed for its soft white sands and crystal-clear waters. Head to Curacao for its iconic Handelskade waterfront in Willemstad, where brightly painted Dutch-style buildings meet turquoise seas.
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Puerto Vallarta vs Cancun – which is better?
Puerto Vallarta and Cancun are two of the most popular destinations in Mexico. You can’t really do both on the same trip - they’re on different sides of the country. It’s a case of favoring one over the other, and it really boils down to what type of vacation you’d like to have.
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Luxury Travel Experiences in the Caribbean You Haven’t Heard Of
The Caribbean is synonymous with white-sand beaches, turquoise waters, and luxury resorts. But beyond the well-trodden tourist hotspots, this region is home to a treasure trove of unique and lesser-known experiences. If you’re seeking privacy, the Grenadines and the Exumas are secluded and exclusive. You may find yourself staying on a secluded private island or chartering a yacht to explore untouched cays.
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Beyond Puerto Vallarta: Mexico’s Emerging LGBTQ+ Destinations
Puerto Vallarta has long reigned as Mexico's premier LGBTQ+ destination, with its picturesque malecon, flawless climate and Zona Romántica: the ever-buzzing gay district. For American LGBTQ+ travelers in particular, PV is a destination you have to visit at least once in a lifetime. If you’re seeking fresh luxury experiences beyond PV's familiar charms, Mexico has so much to offer.
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Puerto Rico vs. Barbados – which is better?
When choosing between Puerto Rico and Barbados for your next Caribbean getaway, it can be tricky to make a decision. Both are very inviting and they both have different charms. It takes around 2 hours to fly between the islands so it’s advisable to pick one over the other. We generally don’t advise combining both islands in the same trip. So, what exactly differentiates one island from the other?
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The Best Gay Beaches in Mexico
Mexico is Latin America's most popular LGBTQ+ travel destination. It combined stunning Pacific and Caribbean coastlines, gay legal protections dating to 1871, and a thriving circuit party scene that attracts international travelers year-round. From Puerto Vallarta's legendary Zona Romántica to Mexico City’s sprawling gay scene, Mexico has a lot to offer LGBTQ+ travelers.
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Gay-Friendly Travel in Barbados: “It’s a very welcoming island”
Jack Dunmore gave Out Of Office the challenge of putting together a week of R&R with enough to keep three friends occupied if the beach was too much like hard work.
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How We Vet Hotels for LGBTQ+ Clients
At Out Of Office, we do not rely on brochures or generic reviews. Every hotel we recommend has been carefully considered through years of firsthand experience, client feedback, and trusted relationships on the ground. Finding the right hotel is about more than five-star ratings. For LGBTQ+ travelers, it is about feeling genuinely welcome. Here is how we vet every property before we recommend it. We see it for ourselves Whenever possible, we visit.
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How Mustique Became the Most Luxurious Island in the Caribbean
Mustique is the most exclusive destination in the Caribbean. But how did this 1,400-acre speck of land transform into a playground for royalty, celebrities, and the global elite? The story of Mustique encompasses the British royal family, David Bowie, and an eccentric aristocrat who kick-started the whole thing. The story has been told by Princess Margaret’s Lady in Waiting in her fabulous memoir, and also in the last season of The Crown.
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Best Gay Bars and Beach Clubs in Puerto Vallarta
Puerto Vallarta has earned its place as one of the world’s most popular LGBTQ+ destinations. Once a quiet fishing district, Zona Romántica has transformed into the beating heart of LGBTQ+ life in Puerto Vallarta. Its cobblestone streets, pastel façades, and beachfront cafés give it a village-like quality, but it’s the buzzing nightlife that draws travelers back year after year.
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The Best Gay-Friendly Caribbean Islands
The Caribbean, with its crystal waters, flawless weather and white sand beaches, is a dream destination for many travelers. With a temperate climate year-round, the Caribbean ensures consistent appeal regardless of the season. The beaches are famed for having pristine white sand, pink sand (e.g., Pink Sands Beach in Harbour Island, Bahamas), and even dramatic black volcanic sand (e.g., beaches in St. Vincent and the Grenadines).
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Plan Your Gay Honeymoon in Cabo
Cabo sits three hours by flight from Los Angeles. You can be drinking cocktails on Medano Beach six hours after leaving San Francisco. The infrastructure is geared towards English speakers, especially North Americans. Servers, staff, and concierges have handled same-sex couples long enough that your arrival requires no explanation. The weather holds steady between November and April. Whale watching peaks from December through March. The water is warm year-round.
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 $8,895 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 $4,430 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 $7,340 per person View tripWhere to stay in Caribbean
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.