7 days tailor made from £3350 pp
From £3350 pp
The Caribbean is a melting pot of diverse islands. From the plush private islands of Mustique, to the iconic destinations of Barbados and St Lucia, the Caribbean is one to head to for year-round sun.
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 can be a tricky destination for LGBT+ travellers so be sure to speak to one of our expert team for the latest advice. Having said that there are plenty of friendly places to stay in both Caribbean islands where being gay is legal.
The Caribbean is above and beyond pure paradise. Known for pristine natural beauty – think sugar-white beaches and luxe palm trees – the Caribbean has everything you need for R&R. At first glance, the different islands may appear similar but each has distinct personalities offering a truly unique experience.
Why not island-hop in the beautiful Bahamas where you can witness the ‘swimming pigs’ and rose hue beaches. For one of the most LGBT-friendly destinations in the Caribbean, Aruba and Curacao welcome LGBT guests with open arms. For a dose of green, including luscious landscapes and tropical rainforests the Dominican Republic and Puerto Rico have the best.
Meet the Aztecs in the fascinating historical sites in Mexico City and Cancun. For that next level of indulgence, Barbados, Mustique and St Lucia may offer exactly what you are looking for. The Caribbean has something for everyone, what more could you want?
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
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 colorful 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
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...
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 presents a complex landscape for LGBTQ+ travelers, with each island offering a different level of acceptance and legal protections. While many Caribbean nations have historically had conservative attitudes towards LGBTQ+ issues, there has been a growing shift toward greater acceptance and inclusivity, particularly in more tourist-focused areas. Some countries have made significant strides in LGBTQ+ rights, with laws decriminalizing same-sex sexual activity and legalizing same-sex marriage, while others remain more restrictive.
Destinations like Puerto Rico, Aruba, and Barbados have gained reputations for being more LGBTQ+ friendly, with vibrant gay scenes, inclusive resorts, and popular Pride events that attract visitors from around the world. Puerto Rico, as a U.S. territory, offers legal protections for LGBTQ+ individuals, including marriage equality, making it one of the most welcoming destinations in the region. The Dominican Republic, known for its stunning beaches and luxury resorts, has a growing LGBTQ+ tourism industry, especially in places like Punta Cana, where same-sex couples can enjoy an inclusive environment.
However, many other Caribbean islands, while they may offer beautiful landscapes and unique cultural experiences, still have laws that criminalize same-sex sexual activity or lack legal protections for LGBTQ+ individuals. Social acceptance varies widely, and LGBTQ+ travelers should exercise caution in more conservative areas, particularly outside major tourist centers.
Despite these challenges, the Caribbean remains a popular travel destination, with some islands offering safe and inclusive spaces where LGBTQ+ individuals can enjoy the region’s natural beauty, luxury resorts, and rich cultural experiences. As awareness grows and advocacy continues, many Caribbean nations are slowly moving toward greater acceptance, making the region an exciting and evolving destination for LGBTQ+ travelers seeking both adventure and relaxation.
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 relaxed vibe that makes every moment feel like a dream.
Beyond the beaches, history buffs can dive into the past at iconic landmarks across the region. One standout is the ancient city of Chichen Itza, located in Cancun, Mexico. This UNESCO World Heritage Site is one of the most well-preserved examples of Mayan architecture and culture. Visitors can marvel at the grandeur of El Castillo, the towering step pyramid, and explore the Temple of the Warriors and the sacred cenote that holds centuries of history.
Whether you’re soaking up the sun or stepping back in time, the Caribbean offers an irresistible mix of relaxation and discovery.
One of the greatest joys of the Caribbean is its versatility—you can fill your days with adventure or simply relax to your heart’s content. For those seeking variety, island hopping is a must. With multi-centre trips, you can explore the unique character of each island, from the lush rainforests of Dominica to the vibrant nightlife of Barbados.
For the more active traveler, the Caribbean’s turquoise waters are an open playground. A wide range of watersports awaits, from kayaking and paddleboarding to snorkeling and diving among colorful coral reefs. Whether you’re gliding across the surface or exploring the depths, there’s no shortage of ways to connect with the stunning seascape.
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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