Anguilla
Anguilla Travel Guides
Written by the specialists who plan our trips to Anguilla: where to go, when, and what is worth knowing before you book.
All Anguilla Travel Guides
Best Caribbean Islands for Winter Sun
As the chill of winter settles in, a trip to the Caribbean might solve all your problems. Why shiver in a freezing cold city when you could be sitting on a beach in Aruba? No tan can rival a winter tan: it’s a sign of sophistication. What’s the weather like in the Caribbean during winter, we hear you ask?
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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 an eccentric aristocrat who kick-started the whole thing. The story has been told by Princess Margaret’s Lady in Waiting in her fabulous memoir, and also in the last season of The Crown.
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Is Anguilla Gay Friendly?
Anguilla, a tranquil gem in the Caribbean, is celebrated for its pristine beaches, luxury resorts, and relaxed atmosphere. But how welcoming is it for LGBTQ+ travelers? Let’s explore what makes Anguilla a promising destination for gay visitors, while also considering its cultural nuances and legal environment.
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Gay Sailing Charters in the Caribbean: Luxury Yacht Experiences
The Caribbean offers more straightforward sailing conditions for LGBTQ+ travelers than most ocean destinations. Island nations here range from actively welcoming (St Barths, US Virgin Islands) to legally hostile (Jamaica), but the luxury yacht charter infrastructure operates with professional neutrality regardless of local attitudes. Most crews working the high-end charter circuit come from Europe, Australia, or the US, bringing service standards that don't vary based on passenger orientation.
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Trips through Anguilla
Barbados & Antigua: Caribbean Jewels
Tailor-made VacationTwelve days across two islands built on completely different relationships with the sea: Antigua's three hundred and sixty-five beaches and Barbados's working coastline of fishing towns and surf breaks.
12 days tailor-made from $5,880 per person View trip
Classic Caribbean: Aruba and Curacao
Tailor-made VacationRenowned for offering the quintessential Caribbean experience – white sands, swaying palm trees, and crystal-clear waters – Classic Caribbean: Aruba and Curacao forms one of our favorite twin-center vacations. These islands invite you to immerse yourself in natural beauty while indulging in world-class hospitality, all set against the stunning backdrop of the Caribbean Sea. Aruba and Curacao are incredibly LGBTQ+ friendly, making them standout destinations for inclusive travel.
7 days tailor-made from $4,430 per person View trip
Cap Juluca, A Belmond Hotel
Luxury HotelCap Juluca sits directly on Maundays Bay, widely considered one of the finest beaches in the Caribbean, its white Moorish-inspired architecture rising against the sand. Every building on the property seems designed to disappear into the view rather than compete with it. Rooms, suites, and villas are spread along the shoreline, giving most accommodations direct beach access, a rarity even among Caribbean resorts of this caliber.
View tripThe hard part is not finding a beautiful place. It is finding the right one for you.
Frequently asked questions
Traveling with Out Of Office
What does Out Of Office do?
Out Of Office is a luxury LGBTQ+ travel company specializing in tailor-made vacations and extraordinary journeys around the world. We create bespoke luxury vacations, LGBTQ+ honeymoons, safaris, cruises, beach escapes, private tours and group trips, with every itinerary designed around you. Our travel specialists combine global expertise, first-hand destination knowledge and trusted local partners to create seamless, highly personalized experiences.
Is Out Of Office a gay travel agency?
Out Of Office is an LGBTQ+ owned and run luxury travel specialist, with particular expertise in gay and LGBTQ+ travel. We understand the additional considerations that can come with traveling as an LGBTQ+ person or couple, from local laws and customs to finding genuinely welcoming hotels and experiences.
We welcome every traveler, including friends, families and allies. Many of our clients are not members of the LGBTQ+ community, but choose Out Of Office for our luxury travel expertise, personalized service and discretion.
Do you create tailor-made LGBTQ+ vacations?
Yes. Every tailor-made trip with Out Of Office is designed from scratch around your interests, travel style, budget and the way you want to experience a destination. We can arrange luxury hotels, private transfers, flights, guides, excursions, cruises and special experiences as part of one personalized itinerary. The journeys shown on our website are there to inspire you rather than restrict you; only clearly identified group departures operate as fixed itineraries.
How do you choose LGBTQ+ friendly hotels and destinations?
We combine first-hand destination knowledge with trusted local expertise to recommend luxury hotels, resorts and experiences where LGBTQ+ travelers can feel informed and welcome. We also consider the laws, customs and attitudes of each destination, because LGBTQ+ rights and experiences differ around the world. Our team regularly visit many of the properties we work with and where a destination requires greater awareness, we give you clear and considered advice so that you can make an informed decision about where and how you travel.
We plant trees for every booking
For every booking made with Out Of Office we commit to planting trees in your name to help reduce the impact of travel on future generations. You'll even get a link to see where your trees are planted in the world via our partner Ecologi.
We donate to Rainbow Railroad with every booking
Rainbow Railroad helps LGBTQ+ people escape state-sponsored violence and persecution. A donation goes with every trip we sell, funded by us and never added to your price.
Start Planning Your Trip
Tell us where you would love to go, when you are thinking of traveling and what kind of trip you have in mind. One of our LGBTQ+ travel specialists will create a tailor-made itinerary designed around your destination, style and preferences.
One named specialist, first inquiry to homecoming. No call center, and nothing is charged until you decide to book.