Caribbean
Caribbean Travel Guides
Written by the specialists who plan our trips to Caribbean: where to go, when, and what is worth knowing before you book.
All Caribbean Travel Guides
Showing 49–54 of 54
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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The Best Gay Christmas Vacations
Christmas is a time for family, food and excessive shopping. It's also a great time to go on holiday and have some last-minute fun before another year ends. Whether you're looking to escape the cold for warmer climes or visit somewhere snowy and festive, we've got you covered. In some of our featured Christmas destinations, we've included seasonal hotels - including a hotel made of ice that melts after winter!
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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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Celebrity blogger Perez Hilton on traveling as a gay parent with children
Celebrity blogger Perez Hilton is known for being outspoken and for being at the forefront of celeb culture. But as a single gay parent traveling with kids is he more reserved and does he approach his travel plans differently? This interview was published in 2018 What's your experience of traveling as a gay man? I love going to the most foreign places.
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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.
ReadTrips through Caribbean
Ultimate Luxury Mexico: Punta Mita, Los Cabos & Riviera Maya
Tailor-made VacationThree coastlines, one itinerary, entirely shaped around you. Move between three of Mexico's most distinct coastal regions, each with its own rhythm. From the private peninsula of Punta Mita to the dramatic cliffs of Los Cabos and the reef-lined shore of the Riviera Maya, the trip is built entirely around the version of Mexico you want to see.
9 days tailor-made from $8,920 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 $4,445 per person View trip
Miami & Caribbean Cruise
Tailor-made VacationExperience Miami's welcoming energy, Caribbean sailing, and island time in the Bahamas, all in one luxury trip. This nine-day trip opens in Miami, a city whose LGBTQ+ history runs deep along South Beach and Ocean Drive, where Art Deco facades and an easy, sun-soaked pace set the tone for the days ahead.
9 days tailor-made from $7,360 per person View tripWhere to stay in Caribbean
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 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.