7 days tailor made from $4,490 pp
From $4,490 pp
The Caribbean spans thousands of islands, and no two deliver the same trip.
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.
Barbados runs on nightlife, rum, and a culinary scene that holds its own against anywhere in the region. Mustique is built for total privacy, the kind that draws royalty and rock stars who want to disappear for a week. Aruba and Curacao trade in easy, laid-back luxury, with some of the most consistently gay-friendly laws and attitudes in the region.
Further south, St. Lucia and the Grenadines swap white sand for volcanic peaks and rainforest, a different Caribbean entirely.
Gay-friendliness varies from island to island and resort to resort. We know which ones actually deliver on it, and we build every itinerary around that.
While winter tightens its grip on Europe and North America, this stretch of sea stays warm and does year-round.
That alone makes it one of the world’s great luxury escapes, but the real draw is the range: sugar-white beaches on one island, pink sand on the next, black volcanic shores on another, all within a short flight of each other.
Every trip we build here is tailor-made. What follows is a starting point, not a fixed itinerary.
Tailor-made Vacation
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 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
Nine 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...
Tailor-made Vacation
This 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...
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 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...
Tailor-made Vacation
Eight days across the volcanic peaks, quiet rainforest, and cacao hills of St Lucia’s south and north. The south holds the island’s signature view: the twin Pitons rising directly from the sea at Soufriere, with a working volcano and a...
Tailor-made Vacation
Two 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...
Tailor-made Vacation
Turks 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...
Tailor-made Vacation
Four 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...
Tailor-made Vacation
The 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...
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
Crystal 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 vacation. This enchanting journey invites you to immerse yourself in...
Tailor-made Vacation
Riviera 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 –...
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...
Tailor-made Vacation
Experience 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...
Tailor-made Vacation
Shaped by a rich tapestry of global influences including African, Spanish, and Taino Indian flavors, 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
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 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....
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 us
Jaike Rowe
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.
Necker Island is the extreme version of Caribbean privacy. Richard Branson’s private island in the British Virgin Islands buys out the entire property: every villa, every staff member, every inch of beach, with nobody else on it. Guests get the run of the place, from the Great House to the tennis courts to the kite surfing lagoon, all staffed and run as if it were built for them alone.
It’s less a hotel stay than a full lifestyle rental. Every detail, from the daily schedule to the menu, gets built around one group at a time. That’s the whole point, and it’s why it draws royalty, musicians, and heads of state who want a week where nobody else is around.
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.
Call our travel experts on +44 (0)20 7157 1570
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