The Caribbean
Luxury Caribbean Tours
Suggested trips through the Caribbean, each one a starting point that our LGBTQ+ travel specialists tailor around your dates, pace and preferences.
Featured Tours in The Caribbean
Classic Caribbean: Aruba and Curacao
Renowned 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.
7 days | From $4,445 pp
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Barbados & Antigua: Caribbean Jewels
Twelve 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 | From $5,895 pp
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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
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
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 $3,780 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 $1,720 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 $3,925 per person View trip
Reading on the 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
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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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?
ReadTell us how you like to travel. We will shape the trip around it.
Frequently asked questions
Traveling with Out Of Office
What does Out Of Office do?
Out Of Office is a luxury LGBTQ+ travel company specializing in tailor-made vacations and extraordinary journeys around the world. We create bespoke luxury vacations, LGBTQ+ honeymoons, safaris, cruises, beach escapes, private tours and group trips, with every itinerary designed around you. Our travel specialists combine global expertise, first-hand destination knowledge and trusted local partners to create seamless, highly personalized experiences.
Is Out Of Office a gay travel agency?
Out Of Office is an LGBTQ+ owned and run luxury travel specialist, with particular expertise in gay and LGBTQ+ travel. We understand the additional considerations that can come with traveling as an LGBTQ+ person or couple, from local laws and customs to finding genuinely welcoming hotels and experiences.
We welcome every traveler, including friends, families and allies. Many of our clients are not members of the LGBTQ+ community, but choose Out Of Office for our luxury travel expertise, personalized service and discretion.
Do you create tailor-made LGBTQ+ vacations?
Yes. Every tailor-made trip with Out Of Office is designed from scratch around your interests, travel style, budget and the way you want to experience a destination. We can arrange luxury hotels, private transfers, flights, guides, excursions, cruises and special experiences as part of one personalized itinerary. The journeys shown on our website are there to inspire you rather than restrict you; only clearly identified group departures operate as fixed itineraries.
How do you choose LGBTQ+ friendly hotels and destinations?
We combine first-hand destination knowledge with trusted local expertise to recommend luxury hotels, resorts and experiences where LGBTQ+ travelers can feel informed and welcome. We also consider the laws, customs and attitudes of each destination, because LGBTQ+ rights and experiences differ around the world. Our team regularly visit many of the properties we work with and where a destination requires greater awareness, we give you clear and considered advice so that you can make an informed decision about where and how you travel.
Our Experts
As specialists in navigating the complex Caribbean, we ensure that LGBTQ+ travelers enjoy a safe and unforgettable experience, connecting them with the most welcoming and inclusive destinations in the region.
Aruba and Curacao stand out as particularly welcoming islands for the LGBTQ+ community, offering a blend of stunning beaches, inclusive resorts, and a warm, open-minded atmosphere.
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.