Caribbean
Luxury Caribbean Tours
Suggested trips through Caribbean, each one a starting point that our LGBTQ+ travel specialists tailor around your dates, pace and preferences.
Most begin in the Caribbean, Mexico and Bahamas, and many combine more than one country.
Tours in Caribbean
Showing 25–34 of 34
Luxury Yucatán Tour: Chichén Itzá, Mayakoba & Tulum
Tailor-made VacationColonial Mérida, two great Mayan cities, and a stretch of coastline near Tulum. This carefully curated journey takes you from the vibrant streets of Mérida through time itself to stand before one of the world's most magnificent archaeological treasures—Chichén Itzá—before concluding on the pristine shores of the Riviera Maya. Mérida rarely gets top billing next to Chichén Itzá, but its warmth, in both climate and welcome, makes it the right place to start.
8 days tailor-made from $4,625 per person View trip
Ultimate Luxury: St Lucia, North to South
Tailor-made VacationEight days across the volcanic peaks, quiet rainforest, and cacao hills of St Lucia's south and north. The south holds the island's signature view: the twin Pitons rising directly from the sea at Soufriere, with a working volcano and a rainforest pressing in behind them.
8 days tailor-made from $7,595 per person View trip
Discover Mexico City
Tailor-made VacationMexico City is a destination that embraces all who visit, a place where history, art, and gastronomy thrive in a spirit of inclusivity. This thoughtfully curated itinerary invites you to explore the city in unparalleled style. From the echoes of ancient civilizations to the avant-garde energy of its modern streets, Mexico City is a truly enchanting destination.
6 days tailor-made from $4,225 per person View trip
Luxury Puerto Rico
Tailor-made VacationWith its world-renowned stretches of white-sand beach, rich cultural heritage, and a range of luxury accommodations, Puerto Rico is one of the Caribbean’s best destinations for a truly luxurious, LGBTQ+-friendly island getaway. Our luxury Puerto Rico itinerary is meticulously crafted to showcase the finest aspects of this enchanting destination, and is one of our most popular escapes with our clients.
9 days tailor-made from $4,230 per person View trip
Puerto Vallarta And Riviera Nayarit
Tailor-made VacationThis fantastic itinerary takes you to both Puerto Vallarta and the Riviera Nayarit, two of the most up-and-coming destinations in Mexico. Nestled along Mexico's stunning Pacific coast, Puerto Vallarta has firmly established itself as one of the country's most sought-after destinations.
11 days tailor-made from $3,905 per person View trip
Miami and Puerto Rico
Tailor-made VacationExperience the epitome of luxury with our exclusive twin-center itinerary, featuring two of the USA's premier destinations: Miami and Puerto Rico. These vibrant locales offer a captivating blend of dazzling splendor and stunning coastal landscapes, making them perfect for discerning travelers seeking an unforgettable getaway. Miami, renowned as the epitome of colorful luxury along the Caribbean coast, beckons with its dazzling array of luxury properties and vibrant cultural scene.
9 days tailor-made from $3,450 per person View trip
Yucatan Adventure: Cancun, Uxmal, Mérida & Riviera Maya
Tailor-made VacationA flamingo reserve, two great Mayan cities, and colonial Mérida, before the trip settles onto the coast: Embark on an unforgettable journey through the heart of the Yucatan Peninsula with this exclusive itinerary, tailored for those seeking an immersive blend of culture, history, and natural beauty. Few regions in Mexico pack in as much variety as the Yucatán Peninsula, and this nine-day trip is built to move through most of it.
9 days tailor-made from $3,505 per person View trip
LGBTQ+ Puerto Rico Culinary Tour: San Juan, Ponce
Tailor-made VacationPuerto Rico's food carries three distinct histories at once: Taino root vegetables and cooking techniques, Spanish stews and sofrito, and West African ingredients brought through the slave trade, most visibly in dishes built on plantain and salted cod. That layering is still legible on the plate. Mofongo, made from mashed green plantain, and arroz con gandules, rice cooked with pigeon peas, both trace directly back to it.
7 days tailor-made from $4,655 per person View trip
Art & Culture in Mexico City: Luxury Discovery Tour
Tailor-made VacationAncient pyramids that predate the Aztecs, Frida Kahlo's world in Coyoacan, and Mexico City's LGBTQ+ heart in Zona Rosa, woven into five days. This trip opens in the historic center, where colonial-era cathedrals and world-class museums sit within walking distance of each other. The Zócalo anchors the district, one of the largest squares in Latin America, flanked by the Metropolitan Cathedral and the National Palace, where Diego Rivera's murals trace Mexico's history.
5 days tailor-made from $1,920 per person View trip
Discover Cancun: Chichén Itzá, Tulum & the Riviera Maya
Tailor-made VacationCancun's beaches, two great Mayan sites, and a welcoming corner of Mexico's Caribbean coast. This eight-day trip opens on the white sand and turquoise water that made Cancun one of Mexico's best-known destinations, part of a Riviera Maya coastline that has become an increasingly comfortable base for LGBTQ+ travelers, even without a dedicated gay neighborhood of its own. From the resort, the trip reaches into the region's history.
8 days tailor-made from $3,915 per person View tripWhere to stay in Caribbean
Reading on Caribbean
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.
Read
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.
Read
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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Anthony S.
Super client centred service. From first contact I have had warm, efficient, friendly and flexible service.
John
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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 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.