Caribbean
Luxury Caribbean Holidays
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.
Holidays in Caribbean
Showing 25–34 of 34
Luxury Yucatán Tour: Chichén Itzá, Mayakoba & Tulum
Tailor-made HolidayThis 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, known for its warmth — not just in its climate but in its people — sets the tone for this cultural odyssey.
8 days tailor-made from £3,495 per person View trip
Ultimate Luxury: St. Lucia
Tailor-made HolidaySt. Lucia, a breathtaking gem of the Caribbean, seamlessly combines lush natural landscapes, vibrant culture, and world-class luxury to create an unforgettable escape. This thoughtfully designed itinerary invites you to experience the island’s contrasting charms, from the serene beaches and tropical gardens of the north to the dramatic volcanic peaks of the Pitons in the south, all whilst enjoying the finest luxury that the country has to offer.
1 day tailor-made from £8,950 per person View trip
Discover Mexico City
Tailor-made HolidayMexico 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 £3,195 per person View trip
Luxury Puerto Rico
Tailor-made HolidayWith 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 £3,200 per person View trip
Puerto Vallarta And Riviera Nayarit
Tailor-made HolidayThis 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 £2,950 per person View trip
Miami and Puerto Rico
Tailor-made HolidayExperience the epitome of luxury with our exclusive twin-centre 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 travellers seeking an unforgettable getaway. Miami, renowned as the epitome of colourful luxury along the Caribbean coast, beckons with its dazzling array of luxury properties and vibrant cultural scene.
9 days tailor-made from £2,610 per person View trip
Yucatan Adventure: Cancun, Uxmal, Mérida & Riviera Maya
Tailor-made HolidayEmbark 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. This adventure invites travellers to explore the ancient wonders of Mayan civilisation, indulge in the vibrant flavours of Mexican cuisine, and unwind on the pristine beaches of the Riviera Maya.
9 days tailor-made from £2,650 per person View trip
LGBTQ+ Puerto Rico Culinary Tour: San Juan, Ponce
Tailor-made HolidayPuerto 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 £3,520 per person View trip
Art & Culture in Mexico City: Luxury Discovery Tour
Tailor-made HolidayAncient 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 centre, 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 £1,450 per person View trip
Discover Cancun
Tailor-made HolidayCrystal clear waters, beautiful blue skies, and white sandy beaches. Need we say anymore? Discover the unparalleled beauty and vibrant culture of Cancun in Mexico with this meticulously curated luxury holiday. This enchanting journey invites you to immerse yourself in the splendor of Riviera Maya's pristine beaches, explore the majestic ancient ruins of Chichen Itza and Tulum, and indulge in the unique flavors of authentic Mexican cuisine.
8 days tailor-made from £2,960 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 holiday 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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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.