The Caribbean
Caribbean Travel Guides
Written by the specialists who plan our trips to the Caribbean: where to go, when, and what is worth knowing before you book.
All Caribbean Travel Guides
Showing 25–33 of 33
Plan Your Gay Honeymoon in the Caribbean
The Caribbean is a picture-perfect destination for a gay honeymoon. With its sun-drenched beaches, crystal clear waters, and world-class resorts, the Caribbean is a big draw for romantic trips. The Caribbean is home to some of the world’s most romantic beaches. Grace Bay Beach in Turks and Caicos is a picture-perfect beach with pristine waters and upscale beachfront resorts.
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The Best Gay-Friendly Hotels in the Caribbean
The Caribbean is a dream vacation spot with turquoise waters, white sand beaches, and world-class luxury hotels. However, choosing the right accommodation is key to ensuring a truly memorable and inclusive experience. While many islands in the region are big tourist magnets, some islands and hotels are more gay-friendly than others. Caribbean hotels are very varied, from more touristy all-inclusive options to ultra-exclusive hotels and everything in between.
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The Best Luxury Honeymoon Destinations Around the World
Are you dreaming of a honeymoon that exudes luxury and extravagance? Look no further, as we take you on a journey to explore the best luxury honeymoon destinations around the world. From breathtaking villas nestled in the Maldives to exclusive resorts in the Caribbean, these destinations promise an unforgettable experience for couples seeking opulence and romance.
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The Best Things to do in Puerto Rico
Puerto Rico offers plenty of activities and experiences that promise to elevate your vacation to the next level. From lounging on beautiful beaches to exploring ancient ruins, there are a variety of things to do in Puerto Rico. Adventure seekers can get their adrenaline pumping with activities like zip-lining, snorkelling or stand-up paddle boarding. Those looking for more leisurely pursuits can sample the island's unique cuisine or take a historical walking tour.
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Best Gay Honeymoon Destinations 2027 & 2028
At Out Of Office, we specialize in creating exceptional gay honeymoons for couples who want more than just a beautiful destination. Our LGBTQ+ honeymoon specialists have planned thousands of same-sex honeymoons worldwide, giving us unrivaled insight into where offers the perfect balance of romance, privacy, luxury, and genuine inclusivity. With 2027 honeymoon bookings well underway, couples are planning further ahead than ever.
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Best Lesbian Honeymoon Destinations 2027 & 2028
At Out Of Office, we pride ourselves on our unmatched expertise when it comes to creating the most incredible lesbian honeymoons in the world. We know just how challenging it can be to travel as a lesbian, and we're dedicated to making those travel experiences as easy, safe and enjoyable as possible.
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Meet Donnya Piggott: Barbados’ Most Outspoken LGBT+ Activist
Barbados is one of the most beautiful islands in the world, but it's a tricky proposition if you're LGBT+. Homosexuality is illegal in Barbados. Although homophobic laws are rarely enforced, they cast quite a shadow over the island if you're gay, bi or gender nonconforming. Enter Donnya Piggott. Donnya is an outspoken LGBT+ activist from Barbados. She has spearheaded B-GLAD, a public advocacy organization campaigning for LGBT+ rights.
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A video guide to Mustique
If you're looking for a private island escape then look no further than Mustique. A tiny island located in a group called St Vincent & the Grenadines and with a population of only 500 Mustique covers just 2.2 square miles. It has fast developed a reputation of being one of the most exclusive islands in the Caribbean.
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Top Tips for Puerto Rico: We won a trip there. No, really!
James Glynn and Tomek Mossakowski enjoyed a stunning trip to Puerto Rico courtesy of OutOfOffice.com, Puerto Rico Tourism and Norwegian Air. We were so surprised when we won a trip to Puerto Rico. That's because most British people - let's be honest - don't really know where or what Puerto Rico is.
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Trips through the Caribbean
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 $4,420 per person View trip
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 $5,865 per person View trip
Passion in Paradise: St Lucia and Grenada Honeymoon
Tailor-made VacationNine days across St Lucia's volcanic south and Grenada's spice-scented coast, from the Pitons to the nutmeg groves. St Lucia opens the trip with four nights built around the Pitons, the pair of volcanic spires that anchor the island's southwest coast.
8 days tailor-made from $10,815 per person View tripTell us how you like to travel. We will shape the trip around it.
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.
Our Experts
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.
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.
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.