Puerto Rico
Puerto Rico Travel Guides
Written by the specialists who plan our trips to Puerto Rico: where to go, when, and what is worth knowing before you book.
All Puerto Rico Travel Guides
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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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?
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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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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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Plan Your Gay Honeymoon in Puerto Rico
Puerto Rico occupies a singular space in the Caribbean imagination. It's technically stateside, which means no passport shuffling for American travelers, yet the moment you land in San Juan, the air thick with salt and the faint pulse of reggaetón drifting from somewhere unseen, you're unmistakably elsewhere.
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Tropical Destinations Where Gay Couples Can Legally Marry
Thailand became the first Southeast Asian country to legalize same-sex marriage in January 2025, joining a growing list of tropical destinations where gay couples can exchange vows legally. With 38 countries now recognizing marriage equality, LGBTQ+ couples have more stunning tropical options than ever before for their dream destination wedding.
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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 Puerto Rico
Luxury Puerto Rico
Tailor-made VacationWith 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 $4,230 per person View trip
Miami and Puerto Rico
Tailor-made VacationExperience the epitome of luxury with our exclusive twin-center 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 travelers seeking an unforgettable getaway. Miami, renowned as the epitome of colorful luxury along the Caribbean coast, beckons with its dazzling array of luxury properties and vibrant cultural scene.
9 days tailor-made from $3,450 per person View trip
Timeless Puerto Rico: Culture, Coastlines and Canopies
Tailor-made VacationStep 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 $7,870 per person 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.
Our Experts
I can't get enough of Puerto Rico. For me, its beauty is all about its diversity and I'm always surprised by how much variety can be found on one small island. Puerto Rico is a must-visit destination.
If you're looking for pristine beaches, lush jungles, and lively towns you just can't beat Puerto Rico. It's also one of the most gay-friendly Caribbean islands, and somewhere I love sending clients.
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.