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 1–12 of 34
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 trip
Mexico Highlights including Tequila and Puerto Vallarta
Tailor-made VacationIn this itinerary you will discover the highlights of Mexico City, you'll go sailing in Puerto Vallarta, sip tequila in Tequila and visit the city abandoned around the 8th century, Teotihuacan to experience the history of the region. Mexico City sits at the heart of the country. It is a bustling megalopolis filled with vibrant cantinas, captivating museums, innovative dining options, and the opportunity to explore ancient canals by boat.
12 days tailor-made from $3,745 per person View trip
Barbados & Antigua: Caribbean Jewels
Tailor-made VacationTwelve days across two islands built on completely different relationships with the sea: Antigua's three hundred and sixty-five beaches and Barbados's working coastline of fishing towns and surf breaks.
12 days tailor-made from $5,880 per person View trip
The Bahamas
Tailor-made VacationEnter the tropical haven of The Bahamas, a stunning archipelago that epitomizes paradise. With sugar-white beaches and crystal-clear waters, each island offers its own slice of heaven, making The Bahamas a dream destination for travelers seeking both adventure and relaxation. Whether you're looking for thrilling water sports or simply want to unwind in a hammock by the ocean, The Bahamas promises a range of unforgettable experiences set against a backdrop of natural beauty.
10 days tailor-made from $1,715 per person View tripMoments in Caribbean
Casa Azul
Frida Kahlo's former home is a treasure trove of art history and a must-visit spot in Mexico City.
How to Visit Flamingo Island in Aruba
Izta-Popo National Park
Acres of awe-inspiring natural landscapes waiting to be explored.
Diving in the Caribbean
Discover some of the best dive sites on the planet
Mexico City & Yucatán Tour: Teotihuacan & Riviera Maya
Tailor-made VacationMexico City's history and the Riviera Maya's coastline, woven into one itinerary. This ten-day journey opens in Mexico City, a capital that pairs its Aztec and colonial layers with one of Latin America's most established LGBTQ+ scenes. Days are spent in the Zocalo and along Paseo de la Reforma, tracing the city's history through the National Palace's murals and the ruins of the Templo Mayor, tucked just behind the cathedral.
10 days tailor-made from $3,785 per person View trip
Passion in Paradise: St Lucia and Grenada Honeymoon
Tailor-made VacationNine days across St Lucia's volcanic south and Grenada's spice-scented coast, from the Pitons to the nutmeg groves. St Lucia opens the trip with four nights built around the Pitons, the pair of volcanic spires that anchor the island's southwest coast.
8 days tailor-made from $10,845 per person View trip
Cabo: The Out Of Office Collection
Cabo Tailor-made VacationCabo has emerged as one of Mexico's top luxury destinations. It offers a unique blend of vibrant nightlife and breathtaking natural beauty, with a small gay scene to boot. From clubs that encourage conga lines and tequila shots, to peaceful mornings spent boating alongside dolphins and whales, Cabo has something for everyone. The beach is a hub of activity, with options like watersports, parasailing, and horseback riding readily available.
7 days tailor-made from $4,870 per person View trip
Discover Turks & Caicos and The Bahamas
Tailor-made VacationThis bespoke journey offers you the opportunity to explore two of the Caribbean's finest destinations: Turks and Caicos and Harbour Island in the Bahamas. Begin in Turks and Caicos, where you will experience the secluded beauty of Grace Bay and the world-class service of the island's resorts.
10 days tailor-made from $11,895 per person View trip
Riviera Maya: The Out Of Office Collection
Riviera Maya Tailor-made VacationRiviera Maya is the place to be on Mexico's Caribbean coast and an easy, welcoming stretch of coastline for LGBTQ+ travelers, even where the destination does not have the dedicated gay neighborhood of Puerto Vallarta or Mexico City.
7 days tailor-made from $3,770 per person View trip
Timeless Puerto Rico: Culture, Coastlines and Canopies
Tailor-made VacationStep into the heart of the Caribbean with this extraordinary nine-day journey through Puerto Rico, where every moment is designed to inspire. From the cobblestone streets of Old San Juan to the tranquil shores of Vieques, this trip blends history, natural beauty, and a vibrant culture into a seamless celebration of life and exploration.
9 days tailor-made from $7,870 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.
ReadStellar 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.