7 days tailor made from £3350 pp
From £3350 pp
The Caribbean can be a tricky destination for LGBTQ+ travellers, so be sure to speak to one of our expert team for the latest advice. With so many islands to choose from, each with its own unique charm, it’s important to understand how they differ—particularly in terms of gay-friendliness. For example, Aruba, a Dutch overseas territory, upholds the same LGBTQ+ rights as the Netherlands, making it one of the most welcoming destinations in the region. Jamaica, on the other hand, is known to be less accepting, especially if you venture beyond the resorts.
Here at Out Of Office, we truly understand the world you live in, and the world you want to explore. Our attention to detail, exceptional service and deep understanding of both luxury travel and LGBTQ+ travel make us a fantastic choice for those looking for a travel experience where exclusivity meets inclusivity.
The Caribbean is pure paradise, known for its pristine natural beauty—think sugar-white beaches and swaying palm trees. Whether you’re looking for relaxation or adventure, the islands may seem similar at first glance, but each has its own distinct personality, offering a truly unique experience.
Why not explore Barbados, one of the larger islands, known for its buzzing nightlife and exceptional culinary scene? If you’re looking for the most LGBTQ+-friendly destinations in the Caribbean, Aruba and Curaçao are the easiest choices. For lush landscapes and tropical rainforests, the Dominican Republic and Puerto Rico stand out as the best options.
For the ultimate indulgence, Mustique offers exactly what you might be looking for—an ultra-exclusive playground for royalty and rockstars. With such a wide variety of island experiences, it’s impossible to generalise about the Caribbean. One thing is certain, though: while much of Europe and North America freezes, the Caribbean remains enticingly warm.
Tailor-Made Vacation
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 vacations. These islands invite you to immerse yourself in natural beauty while...
Tailor-Made Vacation
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...
Tailor-Made Vacation
St. 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...
Tailor-Made Vacation
Embark on a journey where love flourishes amidst the breathtaking beauty of the Caribbean. This meticulously crafted itinerary invites couples to explore the romantic allure of Saint Lucia and Grenada, two islands renowned for their warm hospitality and stunning landscapes....
Tailor-Made Vacation
Step 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,...
Tailor-Made Vacation
This extraordinary journey combines the vibrant essence of Mexico’s most colourful cities with the breathtaking beauty of its coastal landscapes. Prepare to immerse yourself in the unique blend of cultural marvels and natural wonders that Mexico has to offer, all...
Tailor-Made Vacation
Anguilla 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...
Tailor-Made Vacation
With 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...
Group Trip
Join a gay group trip and sail around the most beautiful islands of The Carribean. Enjoy some tropical designer shopping at Gustavia and sail around the beautiful bays of St. Martin. You’ll sail the reefs of Prickly Pear Cays, scuba...
Tailor-Made Vacation
Enter 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 travelers seeking both adventure and relaxation....
Tailor-Made Vacation
Shaped by a rich tapestry of global influences including African, Spanish, and Taino Indian flavours, Puerto Rico’s culinary landscape offers a truly unique and unforgettable experience. From traditional delights like mofongo and arroz con gandules to innovative interpretations of Caribbean...
Tailor-Made Vacation
Escape on an alluring journey to Miami, Costa Maya, and the Bahamas on this luxury Miami and Caribbean cruise itinerary. Experience Miami’s exhilarating energy before retreating to the Caribbean Sea’s tropical serenity on this luxurious tour. You’ll begin your indulgent...
Millicent Kenworthy-Green
Luxury Travel Expert"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."
Contact usShaye Jolley
Luxury Travel Expert"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."
Contact usThe Caribbean enjoys a tropical climate characterized by warm temperatures year-round, with average highs ranging from 24°C to 29°C (75°F to 84°F). The region experiences a wet season from June to November, often associated with the Atlantic hurricane season, while the dry season from December to May brings sunny skies and minimal rainfall, making it a prime time for travel. Gentle trade winds temper the heat, creating comfortable conditions, and the region’s crystal-clear waters maintain a warm and inviting temperature, perfect for swimming and snorkeling.
The Caribbean is famed for its beaches. From the powdery white sands of the Bahamas to the pink beaches of Barbuda and volcanic black sand shores of St. Lucia, the region offers something for every type of beach lover. These islands are also geographically varied, featuring rainforests, coral atolls, and volcanic landscapes. With over 7,000 islands spanning the Caribbean Sea, you can spend a lifetime exploring the region.
The Caribbean is a haven for tropical adventures, offering something for everyone under the sun. For those who love sunbathing and beachcombing, Barbados and St. Lucia are perennial favorites. These islands are renowned for their crystal-clear waters, pristine sandy beaches, and a luxury hotels.
The Caribbean stands out among global beach destinations. Unlike the vast stretches of uniform sandy beaches found in destinations like Australia or Southeast Asia, the Caribbean offers a remarkable variety, from pristine white sands to pink and black volcanic shores. Its warm, turquoise waters are home to coral reefs, ideal for snorkelling and diving, rivalled only by places like the Maldives. Additionally, the Caribbean’s islands each bring their distinct cultural influences, from Creole and Afro-Caribbean traditions to British and Dutch colonial heritage, ensuring a distinctive experience on every island.
Twin-centre trips in the Caribbean are the perfect way to explore the diversity of the region in one trip. Many islands are close to each other, making it easy to combine two destinations. For example, you could pair the laid-back charm of Barbados with the natural beauty of St. Lucia, enjoying both white sand beaches and volcanic scenery. Alternatively, you might combine Antigua with Dominica’s unspoiled rainforests and waterfalls. With regular flights and ferries connecting neighbouring islands, hopping from one to another is straightforward and adds a sense of adventure to your trip.
A twin-centre trip from Barbados to Bequia combines two of the Caribbean’s most enchanting destinations. Start in Barbados, perhaps the most happening Caribbean island. After exploring its restaurants, historic plantation houses, and turquoise waters, take a short flight to the charming island of Bequia in the Grenadines. Known for its relaxed, unspoiled beauty, Bequia gives you a more tranquil experience, with secluded beaches, hills, and a close-knit island community.
For a truly unparalleled experience, why not hire out Necker Island? This ultra-exclusive retreat is one of the most luxurious private islands in the world. Owned by Sir Richard Branson, the island offers an unparalleled escape with a price tag to match—$42,000 per night ensures an experience reserved for the few who truly want to indulge.
Necker Island is more than just a getaway; it’s a lifestyle. With world-class service, breathtaking views, and endless opportunities for personalized adventures, it’s a destination where privacy meets extravagance. And, of course, the saying holds true: what happens on Necker stays on Necker.
Getting to the Caribbean is relatively easy, as many of the major islands are well-connected to international airports, making the region easily accessible from both Europe and the United States. Flights to popular destinations like Aruba, Curacao, Puerto Rico, the Dominican Republic, and Barbados are available from major hubs across the world, with direct flights from cities like New York, Miami, London, and Toronto.
For travelers from the United States, several major airlines, such as American Airlines, Delta, and JetBlue, offer direct flights to a wide variety of Caribbean islands, with frequent departures from cities on the East Coast, like Miami and New York, as well as other major hubs. For those traveling from Europe, there are also direct flights available, particularly from the UK, Germany, and France, to key destinations in the Caribbean.
In addition to these direct flights, many islands are connected by regional flights, making it easy to hop between destinations once you’ve arrived. Smaller airports on the islands, such as those in Saint Lucia, Antigua, and Turks and Caicos, are serviced by regional carriers, allowing for seamless travel within the Caribbean. Whether you’re flying directly to your chosen destination or connecting through a nearby island, getting to the Caribbean is convenient, ensuring that your tropical getaway is just a flight away.
We want to ensure you have the best experience with us so we’ll keep working on your itinerary until perfect. You will have your own personal dedicated member of our team who will help build a trip that is bespoke to you.
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