The Caribbean
Luxury Caribbean Holidays
Suggested trips through the Caribbean, each one a starting point that our LGBTQ+ travel specialists tailor around your dates, pace and preferences.
Featured Holidays in The Caribbean
Classic Caribbean: Aruba and Curacao
Renowned for offering the classic Caribbean experience – white sands, swaying palm trees, and crystal-clear waters – Classic Caribbean: Aruba and Curacao forms one of our favourite twin-centre holidays. 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.
7 days | From £3,350 pp
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Caribbean Jewels: Barbados and Antigua
Picture a journey where turquoise waters, golden beaches, and vibrant cultures create the perfect backdrop for an unforgettable adventure. This twin-island itinerary invites you to experience the welcoming charm of the Caribbean, where everyone is free to celebrate love and individuality.
11 days | From £4,445 pp
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Passion in Paradise: St Lucia and Grenada Honeymoon
Tailor-made HolidayNine 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 £8,200 per person View trip
Discover Turks & Caicos and The Bahamas
Tailor-made HolidayThis bespoke journey offers you the opportunity to explore two of the Caribbean's finest destinations: Turks and Caicos and Harbour Island in the Bahamas. Begin in Turks and Caicos, where you will experience the secluded beauty of Grace Bay and the world-class service of the island's resorts.
10 days tailor-made from £8,995 per person View trip
Timeless Puerto Rico: Culture, Coastlines and Canopies
Tailor-made HolidayStep into the heart of the Caribbean with this extraordinary nine-day journey through Puerto Rico, where every moment is designed to inspire. From the cobblestone streets of Old San Juan to the tranquil shores of Vieques, this trip blends history, natural beauty, and a vibrant culture into a seamless celebration of life and exploration.
9 days tailor-made from £5,950 per person View trip
Mustique: Private Island Luxury
Tailor-made HolidayThis curated journey to Mustique invites you to experience one of the Caribbean’s most exclusive destinations. It is a place where privacy is sacred, service is deeply personalised, and every guest is welcomed with warmth and discretion. This eight-day journey invites you into a world that few get to experience, where barefoot beach walks, bespoke yacht days, and candlelit dinners are part of the rhythm of daily life.
8 days tailor-made from £10,895 per person View trip
Luxury Turks & Caicos Experience
Tailor-made HolidayTwo sides of the Turks and Caicos Islands and one unforgettable week. Vibrant reef-fringed Providenciales followed by the private island seclusion of COMO Parrot Cay. Begin in Providenciales, where Grace Bay's world-famous shoreline sets the scene for your first few days. Whether you're snorkeling the barrier reef, exploring the turquoise stillness of Chalk Sound, or simply claiming your stretch of sand, Provo has a way of filling a week without ever feeling rushed.
8 days tailor-made from £5,100 per person View trip
A Gay Honeymoon in Turks and Caicos
Tailor-made HolidayTurks and Caicos works for a honeymoon because it gets the fundamentals right, from the perfect beaches to the unrivalled luxury hotel offerings. These islands occupy a rare position in the Caribbean: Turks and Caicos is a destination that has managed to attract the world's most discerning travellers without losing the qualities that drew them there in the first place.
7 days tailor-made from £6,380 per person View tripMoments in The Caribbean
Four Seasons Yachts
Tailor-made HolidayFour Seasons Yachts operates a 207-meter superyacht carrying 95 suites across 11 decks, delivering hotel-level service in a yacht-sized vessel. The experience mirrors staying at a Four Seasons property that happens to move between ports. Each voyage sails the Mediterranean with overnight stays in marquee harbors and smaller coastal towns that larger cruise ships cannot access.
7 days View trip
The Ritz-Carlton Yacht Collection
Tailor-made HolidayThe Ritz-Carlton Yacht Collection operates three custom-built superyachts delivering hotel-level service in yacht-sized vessels. These ships accommodate 298-448 guests (depending on vessel) in all-suite configurations, positioning between traditional luxury cruises (1,000+ passengers) and true private yachts. The experience mirrors staying at a Ritz-Carlton property that happens to move between ports, with consistent service standards, suite-style accommodations, and dining that doesn't rely on buffets or regimented seating times.
7 days View trip
Ultimate Luxury: St. Lucia
Tailor-made HolidaySt. Lucia, a breathtaking gem of the Caribbean, seamlessly combines lush natural landscapes, vibrant culture, and world-class luxury to create an unforgettable escape. This thoughtfully designed itinerary invites you to experience the island’s contrasting charms, from the serene beaches and tropical gardens of the north to the dramatic volcanic peaks of the Pitons in the south, all whilst enjoying the finest luxury that the country has to offer.
1 day tailor-made from £8,950 per person View trip
Miami & Caribbean Cruise
Tailor-made HolidayEscape on an alluring journey to Miami, Costa Maya, and the Bahamas on this luxury Miami and Caribbean cruise itinerary. Experience Miami's exhilarating energy before retreating to the Caribbean Sea's tropical serenity on this luxurious tour. You'll begin your indulgent Miami and Caribbean holiday at Nobu Hotel Miami Beach, a sophisticated beachfront urban oasis ideally located in the heart of Miami Beach.
9 days tailor-made from £5,550 per person View trip
Luxury Puerto Rico
Tailor-made HolidayWith its world-renowned stretches of white-sand beach, rich cultural heritage, and a range of luxury accommodations, Puerto Rico is one of the Caribbean’s best destinations for a truly luxurious, LGBTQ+-friendly island getaway. Our luxury Puerto Rico itinerary is meticulously crafted to showcase the finest aspects of this enchanting destination, and is one of our most popular escapes with our clients.
9 days tailor-made from £3,200 per person View trip
Miami and Puerto Rico
Tailor-made HolidayExperience the epitome of luxury with our exclusive twin-centre itinerary, featuring two of the USA's premier destinations: Miami and Puerto Rico. These vibrant locales offer a captivating blend of dazzling splendor and stunning coastal landscapes, making them perfect for discerning travellers seeking an unforgettable getaway. Miami, renowned as the epitome of colourful luxury along the Caribbean coast, beckons with its dazzling array of luxury properties and vibrant cultural scene.
9 days tailor-made from £2,610 per person View trip
Reading on the Caribbean
Is the Caribbean Gay Friendly?
There's so much to see and do in the Caribbean. Explore the colonial charm of Old San Juan in Puerto Rico, with its cobblestone streets, pastel-colored buildings, and historic forts like Castillo San Felipe del Morro. In Aruba, relax on Eagle Beach, famed for its soft white sands and crystal-clear waters. Head to Curacao for its iconic Handelskade waterfront in Willemstad, where brightly painted Dutch-style buildings meet turquoise seas.
Read
Luxury Travel Experiences in the Caribbean You Haven’t Heard Of
The Caribbean is synonymous with white-sand beaches, turquoise waters, and luxury resorts. But beyond the well-trodden tourist hotspots, this region is home to a treasure trove of unique and lesser-known experiences. If you’re seeking privacy, the Grenadines and the Exumas are secluded and exclusive. You may find yourself staying on a secluded private island or chartering a yacht to explore untouched cays.
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Puerto Rico vs. Barbados – which is better?
When choosing between Puerto Rico and Barbados for your next Caribbean getaway, it can be tricky to make a decision. Both are very inviting and they both have different charms. It takes around 2 hours to fly between the islands so it’s advisable to pick one over the other. We generally don’t advise combining both islands in the same trip. So, what exactly differentiates one island from the other?
ReadOne named specialist, from the first conversation to the flight home.
Frequently asked questions
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.
Our Experts
As specialists in navigating the complex Caribbean, we ensure that LGBTQ+ travellers 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 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.