Luxury The Caribbean vacations

The Caribbean Luxury Tours & Vacations & Holidays 2025 & 2026

Proudly LGBTQ+ Experts and Welcoming to All Travelers


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.

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 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.


More Trips in The Caribbean

Filter Trips
Luxury Anguilla Escape
Luxury Anguilla Escape

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...

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...

Anthony S.

“Stellar service. Stellar products. Stellar people and it gets so much better when you pick up the phone and call.”

John

“Super client centred service. From first contact I have had warm, efficient, friendly and flexible service.”

Tiberiu

“I’m confident in giving Out Of Office a 5-star review! They are one of the leaders in this space without a doubt.”

Trustpilot 5*

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."

Contact us

Travel Information for The Caribbean

General Information


The 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.

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 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.

What Some People Do In The Caribbean


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.

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

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...

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...

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...

Why book with us?

Personal Service


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

Our 5* Reviews


We pride ourselves in the number of clients that are referred to us by our existing customers. Our 5* Trustpilot rating is important to us, so we encourage you to browse our reviews. They speak for themselves and that's why you are in safe hands.


Make an enquiry


Phone

020 7157 1570

Email


To start planning your luxury trip, tell us more about your travel plans and we'll match you with one of our experienced travel specialists. You can speak to us via phone, email or video call.

Open 7 days a week.


All the prices on our website do not include flights. We can, of course, arrange them for you.


Your trip
Your details

Please enter your destination and details.

  • $2,000-3,000
  • $3,000-5,000
  • $5,000-7,500
  • $7,500-10,000
  • $10,000+