Luxury Tailor-Made Caribbean Vacations vacations

Tailor-Made Caribbean Vacations

Proudly LGBTQ+ Experts and Welcoming to All Travelers


The Caribbean is one of the most popular vacation spots on the planet. The climate, the food, the beaches and the clear blue waters make it an irresistible destination. It can be a bit of a minefield for LGBT+ travellers though. The islands of the Caribbean are not often hailed as gay-friendly destinations. That being said, some are far more welcoming to gay travellers than others.

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.

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In this guide to the most gay-friendly islands in the Caribbean, we'll give you the lowdown on the places with the most gay-friendly laws, the best hotels for gay travellers and much more. From Dutch overseas territories to the former stomping ground of Princess Margaret and David Bowie, we'll introduce you to a series of fabulous places and luxury hotels.

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Five places you need to visit in the Caribbean
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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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Gay Friendly Curacao

Curacao is one of the most gay-friendly islands in the Caribbean. As a Dutch overseas territory, Curacao was governed in accordance with Dutch law: Holland is one of the most liberal countries on earth. The island gained its independence from Holland in 2010, but the locals still have Dutch passports and the island has Dutch political and cultural characteristics.

It’s just 40 miles from the coast of Venezuela. In the capital Willemstad you’ll find many colorful Dutch colonial buildings. It’s also a great beach destination – there are 35 beaches to explore.

The island of Curacao has been inhabited for around 6000 years. It’s been governed by many empires, giving it a notably polyglot culture. The locals speak Dutch, Spanish, Papiamentu (the local language) and English.

Fun fact: Former Curacao governor Albert Kickert decreed that all the buildings of Willemstad must be painted in colorful hues. The city was whitewashed like a Spanish village at that point in time. It turned out that he owned a paint company that gained a huge injection of cash after his decree. Curacao now has laws in place to stop such activities.

Curacao

Curacao

Gay Friendly Aruba

Aruba is a Dutch overseas territory. It’s a more developed island than Curacao. As with Curacao, Aruba is a great destination for winter sun. You’ll find many excellent beaches to explore in Aruba, from quiet ones like Eagle Beach to more buzzing beaches.

Be sure to check out Arashi Beach, or try your hand at surfing and watersports on Hadicurari and Boca Grandi beaches. At the heart of the island is the capital Oranjestad, which hosts weekly folk-themed events and has designer boutiques galore. Check out the Archeological Museum to learn more about fascinating American Indian heritage.

Aruba is one of the most gay-friendly places in the Caribbean. It’s governed in accordance with Dutch law, although it’s been self-governed since 1986. Tourism is the key sector of the Aruban economy. Despite Aruba’s strong links to Holland, you’ll find considerable American influence in Aruba, ranging from the food to the style of the bars.

Aruba

Aruba

Gay Friendly Mustique

Mustique is one of the most glamorous and gay-friendly islands in the Caribbean. Purchased by Colin Tenant in 1958, it became the stomping ground of the upper classes and celebrities. Princess Margaret had a holiday home on the island, and later David Bowie purchased a villa in Mustique.

The fashionable life of the tiny island centred around The Cotton House, and it still does to this day. Formerly a cotton warehouse, The Cotton House was designed in 1968 by Oliver Messel. Some legendary parties have taken place in Mustique. Lady Anne Glenconner, Colin Tenant’s wife, drew attention to Mustique when she published her autobiography, chronicling her husband’s eccentric devotion to bringing Mustique to life.

Mustique is a tiny island and there aren’t that many accommodation options. It’s all about luxury and exclusivity. That being said, the options on offer are quite impressive. If it’s good enough for Princess Margaret it should tick all the boxes.

Mustique

Mustique


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