Luxury The Caribbean vacations

The Caribbean Luxury Tours & Vacations & Holidays 2024 & 2025

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
Aruba and Curacao
Aruba and Curacao

Tailor-Made

Renowned for offering the quintessential Caribbean experience – white sands, swaying palm trees, and crystal-clear waters – Aruba and Curacao form one of our favourite twin-centre Caribbean vacations. These Dutch islands invite you to immerse yourself in natural beauty while...

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

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....

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Travel Information for The Caribbean

Tropical favourites for sun and beaching and Barbados and St Lucia. To immerse yourself in history, the most well-known historical sites include the ancient city of Chichen Itza in Cancun.

One of the main appeals of the Caribbean is that you can do as much or as little as you wish. Island hop in one of our outstanding multi-centre trips. Throughout the Caribbean there’s a variety of watersports available for you to try.

Hire out Necker Island, one of the world’s most exclusive island retreats. Not many people say they have stayed on the $42,000 per night resort owned solely by Sir Richard Branson. What happens on Necker stays on Necker!

    Many of the major islands in the Caribbean have their own international airports. It’s easily accessible from Europe and the United States.

    From the blog

    The World's Most Amazing Hotels
    The World's Most Amazing Hotels

    Finding the right hotel can be tricky. We have some inspirational – not to mention aspirational – places for you to consider. The kind of hotels where you get your own pillow butler, yoga teacher and plunge pool. In other...

    Aruba approves civil unions
    Aruba approves civil unions

    The small island of Aruba in the Caribbean has voted to approve civil unions for same-sex couples. It means for the first time that people will be able to tie the knot in Aruba and extending many of the same...

    Five places you need to visit in the Caribbean
    Five places you need to visit in the Caribbean

    The Caribbean boasts 28 island nations and more than 7,000 individual islands in the region. In terms of luxury, you will be hard pressed to find resorts as lucky to benefit from the year round weather that the Caribbean can...

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