Luxury The Caribbean vacations

The Caribbean Luxury Tours & Vacations & Holidays 2025 & 2026

Proudly LGBTQ+ Experts and Welcoming to All Travelers


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.

Why is The Caribbean a popular luxury travel destination?

? Don't forget that all of our itineraries are totally customized and so this is just an idea of what we can build for you.

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?


More Trips in The Caribbean

Filter Trips
Luxury Puerto Rico
Luxury Puerto Rico

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...

Gay Group Trip: Caribbean Cruise
Gay Group Trip: Caribbean Cruise

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...

The Bahamas
The Bahamas

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....

Puerto Rico Culinary Tour
Puerto Rico Culinary Tour

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...

Miami & Caribbean Cruise
Miami & Caribbean Cruise

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...

Miami and Puerto Rico
Miami and Puerto Rico

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...

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Our Experts

Millicent Kenworthy-Green

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
Shaye Jolley

Shaye 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."

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Travel Information for The Caribbean

The Caribbean LGBTQ+ Rights


The 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.

What Everyone Does In The Caribbean


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.

What Some People Do In The Caribbean


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.

What No One Else Does In The Caribbean


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


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.

From the blog

Is the Caribbean Gay Friendly?
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...

Luxury Travel Experiences in the Caribbean You Haven’t Heard Of
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...

Puerto Rico vs. Barbados - which is better?
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...

Gay-Friendly Travel in Barbados:
Gay-Friendly Travel in Barbados: "It's a very welcoming island”

Jack Dunmore gave OutOfOffice.com the challenge of putting together a week of R&R with enough to keep three friends occupied if the beach was too much like hard work. Nestled on the southeastern edge of the Caribbean, Barbados was a...

How Mustique Became the Most Luxurious Island in the Caribbean
How Mustique Became the Most Luxurious Island in the Caribbean

Mustique is the most exclusive destination in the Caribbean. But how did this 1,400-acre speck of land transform into a playground for royalty, celebrities, and the global elite? The story of Mustique encompasses the British royal family, David Bowie, and...

The Best Gay-Friendly Caribbean Islands
The Best Gay-Friendly Caribbean Islands

The Caribbean, with its crystal waters, flawless weather and white sand beaches, is a dream destination for many travelers. With a temperate climate year-round, the Caribbean ensures consistent appeal regardless of the season. The beaches are famed for having pristine...

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