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 13–24 of 34
Puerto Vallarta: The Out Of Office Collection
Tailor-made VacationPuerto Vallarta is one of the most popular vacation spots for US travelers. Overlooking Banderas Bay and surrounded by the Sierra Madre, it's an impeccable beach destination. You'll find a huge gay scene in Zona Romantica—it's Latin America's biggest gayborhood. As LGBT+ Europeans head to Mykonos, LGBT+ Americans head for Puerto Vallarta. Whether you prefer to call it Puerto Vallarta or simply Vallarta, this destination offers a perfect blend of relaxation and adventure.
7 days tailor-made from $3,520 per person View trip
Mustique: Private Island Luxury
Tailor-made VacationThis curated journey to Mustique invites you to experience one of the Caribbean’s most exclusive destinations. It is a place where privacy is sacred, service is deeply personalized, and every guest is welcomed with warmth and discretion. This eight-day journey invites you into a world that few get to experience, where barefoot beach walks, bespoke yacht days, and candlelit dinners are part of the rhythm of daily life.
8 days tailor-made from $14,410 per person View trip
Los Cabos: Adventure Beyond the Resort
Tailor-made VacationBeneath its resort reputation, Los Cabos holds some of the richest marine life in Mexico and a desert most visitors never see. Los Cabos has built its reputation on resort pools and beachfront cocktails, but the water and the desert surrounding the peninsula hold a different kind of trip entirely, one that queer and trans-focused dive operators in the region have already been running for years.
7 days View trip
Luxury Turks & Caicos Experience
Tailor-made VacationTwo sides of the Turks and Caicos Islands and one unforgettable week. Vibrant reef-fringed Providenciales followed by the private island seclusion of COMO Parrot Cay. Begin in Providenciales, where Grace Bay's world-famous shoreline sets the scene for your first few days. Whether you're snorkeling the barrier reef, exploring the turquoise stillness of Chalk Sound, or simply claiming your stretch of sand, Provo has a way of filling a week without ever feeling rushed.
8 days tailor-made from $6,745 per person View trip
Riviera Maya: A Wellness Retreat
Tailor-made VacationMayan-inspired rituals, a sanctuary for sacred bees, and a cenote lagoon for morning yoga, woven into one retreat. This seven-day retreat is built around a Riviera Maya resort with one of the region's more distinctive wellness programs, anchored by a genuine commitment to Mayan healing tradition rather than a generic spa menu borrowed from elsewhere.
View trip
A Gay Honeymoon in Turks and Caicos
Tailor-made VacationTurks and Caicos works for a honeymoon because it gets the fundamentals right, from the perfect beaches to the unrivalled luxury hotel offerings. These islands occupy a rare position in the Caribbean: Turks and Caicos is a destination that has managed to attract the world's most discerning travelers without losing the qualities that drew them there in the first place.
7 days tailor-made from $8,440 per person View trip
7-Day Frida Kahlo Tour of Mexico: Art, Love & LGBTQ+ Legacy
Tailor-made VacationDiscover the passionate world of Mexico's most famous artist on this immersive journey through Frida Kahlo's life, loves, and revolutionary spirit. From her childhood home in Coyoacán to the streets where she found inspiration, this itinerary celebrates not only her artistic genius but also her groundbreaking role as an LGBTQ+ icon who defied convention at every turn.
7 days tailor-made from $6,615 per person View trip
Four Seasons Yachts
Tailor-made VacationFour Seasons Yachts operates a 207-meter superyacht carrying 95 suites across 11 decks, delivering hotel-level service in a yacht-sized vessel. The experience mirrors staying at a Four Seasons property that happens to move between ports. Each voyage sails the Mediterranean with overnight stays in marquee harbors and smaller coastal towns that larger cruise ships cannot access.
7 days View trip
Mexico Food and Culture Tour: Mexico City, Oaxaca & Huatulco
Tailor-made VacationMexico is a country that embraces diversity, where LGBTQ+ travelers can explore with confidence, knowing that vibrant, inclusive spaces await at every turn. This meticulously curated journey unveils the very best of Mexico—its rich history, stunning landscapes, and, of course, its extraordinary food. Your adventure begins in Mexico City, a metropolis brimming with creative energy and culinary passion.
14 days tailor-made from $7,535 per person View trip
The Ritz-Carlton Yacht Collection
Tailor-made VacationThe Ritz-Carlton Yacht Collection operates three custom-built superyachts delivering hotel-level service in yacht-sized vessels. These ships accommodate 298-448 guests (depending on vessel) in all-suite configurations, positioning between traditional luxury cruises (1,000+ passengers) and true private yachts. The experience mirrors staying at a Ritz-Carlton property that happens to move between ports, with consistent service standards, suite-style accommodations, and dining that doesn't rely on buffets or regimented seating times.
7 days View trip
Mexico Self-Drive Adventure: Mexico City to Baja California
Tailor-made VacationExplore at your own pace with this journey through the heart of Mexico, where ancient wonders, breathtaking landscapes, and intimate wildlife encounters await. This meticulously crafted itinerary showcases the very best of the country - from the vibrant streets of Mexico City to the tranquil waters of Baja California. Your adventure begins in Mexico City, where the past and present intertwine in a symphony of color and culture.
15 days tailor-made from $8,195 per person View trip
Luxury Anguilla Escape
Tailor-made VacationAnguilla is one of the most exclusive destinations in the Caribbean. It's a small island packed with luxury hotels and world-class beaches. As it's so exclusive, Anguilla attracts far less tourism than some of the bigger islands so it has more of an untouched feel.
9 days tailor-made from $9,985 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.