The Caribbean
Luxury Caribbean Holidays
Suggested trips through the Caribbean, each one a starting point that our LGBTQ+ travel specialists tailor around your dates, pace and preferences.
Featured Holidays in The Caribbean
Classic Caribbean: Aruba and Curacao
Renowned for offering the classic Caribbean experience – white sands, swaying palm trees, and crystal-clear waters – Classic Caribbean: Aruba and Curacao forms one of our favourite twin-centre holidays. 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 £3,350 pp
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Caribbean Jewels: Barbados and Antigua
Picture a journey where turquoise waters, golden beaches, and vibrant cultures create the perfect backdrop for an unforgettable adventure. This twin-island itinerary invites you to experience the welcoming charm of the Caribbean, where everyone is free to celebrate love and individuality.
11 days | From £4,445 pp
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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
Riviera Maya: The Out Of Office Collection
Riviera Maya Tailor-made HolidayRiviera Maya is the place to be on Mexico's Caribbean coast. Cancun is the most tourist-friendly part of the country. It's packed with luxury resorts. The sprawling Zona Hotelera is a district that's comprised - as the name suggests - of hotels. Picking the right hotel in Riviera Maya can be somewhat of a challenge. As Riviera Maya is one of our most popular destinations, we've got the inside knowledge.
7 days tailor-made from £2,850 per person View trip
The Bahamas
Tailor-made HolidayEnter the tropical haven of The Bahamas, a stunning archipelago that epitomises paradise. With sugar-white beaches and crystal-clear waters, each island offers its own slice of heaven, making The Bahamas a dream destination for travellers 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 £1,295 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 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.
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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?
ReadOne named specialist, from the first conversation to the flight home.
Frequently asked questions
Travelling with Out Of Office
What does Out Of Office do?
Out Of Office is a luxury LGBTQ+ travel company specialising in tailor-made holidays and extraordinary journeys around the world. We create bespoke luxury holidays, 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 personalised 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 travelling as an LGBTQ+ person or couple, from local laws and customs to finding genuinely welcoming hotels and experiences.
We welcome every traveller, 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, personalised service and discretion.
Do you create tailor-made LGBTQ+ holidays?
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 personalised 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+ travellers 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+ travellers 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 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.