Tailor-made trips for 2027 & 2028
Gay Caribbean Islands & Resorts
Tailor-made, always
Every trip built from scratch around your dates, pace and preferences.
Your own specialist
One named person and a 24-hour number while you travel.
Hundreds of five-star reviews
Rated Excellent on Trustpilot across ten years of LGBTQ+ luxury travel.
Visiting the Caribbean can be difficult for the gay and lesbian traveller depending on which island you choose. From gay friendly Caribbean islands like Curacao to hotels that welcome gay travellers in St Lucia, our expert team can help you choose the best gay holiday in the region.
The Caribbean is the ultimate destination for switching off. Bathe under the Caribbean sun at all times of the year and indulge in the laid-back lifestyle the islands offer, giving you a chance to unwind while sipping the finest cocktails. With hundreds of islands to choose from, you’ll find an abundance of stunning properties and gay Caribbean resorts to stay in. Let us recommend our favourite properties in the Caribbean so you can have the perfect holiday. We only work with the most LGBTQ friendly Caribbean islands, ensuring you have a safe and enjoyable experience. You will find some islands are more gay-friendly than others, such as Aruba and Curacao, where you’ll find small but vibrant gay scenes.
Our Most Popular Caribbean Destinations
Frequently asked questions
About Caribbean
Which countries in Caribbean are most LGBTQ+ friendly?
Of the Caribbean destinations we plan trips to, Equaldex rates Mexico (71), The Caribbean (55) and Bahamas (30) highest for LGBTQ+ equality, on its 100-point Equality Index.
Where should I go in Caribbean?
Our Caribbean itineraries most often feature The Caribbean, Mexico and Bahamas.
Can my trip to Caribbean be tailor-made?
Yes. Everything we plan is tailor-made. Our suggested Caribbean itineraries are starting points: your specialist shapes the countries, the route, the hotels, the pace and the length around your dates and preferences. As a guide, our suggested Caribbean itineraries run from 5 to 15 days.
Can I visit more than one country in Caribbean on one trip?
Yes. Every trip we plan is tailor-made, so you can combine as many countries as you like. Some of our travellers pair Mexico with The Caribbean, or Bahamas with The Caribbean.
Which luxury hotels do you recommend in Caribbean?
Our specialists' current picks across Caribbean include , and , each handpicked for how it welcomes every guest.
Where should I honeymoon in Caribbean?
Our 20 Caribbean honeymoon itineraries most often feature The Caribbean, Mexico and Bahamas, each tailored around the two of you.
Travelling with Out Of Office
What does Out Of Office do?
Out Of Office is a luxury LGBTQ+ travel company specialising in tailor-made holidays and extraordinary journeys around the world. We create bespoke luxury holidays, 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 personalised 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 travelling as an LGBTQ+ person or couple, from local laws and customs to finding genuinely welcoming hotels and experiences.
We welcome every traveller, 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, personalised service and discretion.
Do you create tailor-made LGBTQ+ holidays?
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 personalised 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+ travellers 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.
Stellar service. Stellar products. Stellar people and it gets so much better when you pick up the phone and call.
Anthony S.
Super client centred service. From first contact I have had warm, efficient, friendly and flexible service.
John
I’m confident in giving Out Of Office a 5-star review! They are one of the leaders in this space without a doubt.
Tiberiu
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 travelling 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 enquiry to homecoming. No call centre, and nothing is charged until you decide to book.