Tailor-made Holiday · The Caribbean
Luxury Puerto Rico
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.
At a glance
With 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. From exclusive resort accommodations to curated cultural experiences, every detail has been thoughtfully planned to ensure an unforgettable journey.
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Whether you're indulging in gourmet dining, unwinding with spa treatments, or embarking on exhilarating outdoor adventures, each day offers a new opportunity to immerse yourself in the beauty and luxury of Puerto Rico.
Experience the vibrant energy of San Juan, where historic forts stand as a testament to the island's past. Venture into the heart of the island to explore the lush landscapes of the El Yunque National Forest, where cascading waterfalls and verdant trails await. In Ponce, immerse yourself in the vibrant culture of Puerto Rico's second-largest city. Explore historic landmarks, such as the iconic Parque de Bombas and the elegant Teatro La Perla.
Day by day
This is a sample plan, not a fixed departure. Days can be added, removed or reordered, and almost every client changes something. Prices are an entry-level guide; your quote will be exact.
Day 1-3: San Juan
Nestled on the edge of the Condado Lagoon, and enjoying easy access to San Juan’s charming Old Town, O:live Boutique Hotel is one of the finest examples of casual luxury anywhere in Puerto Rico. With interiors inspired by the island’s natural landscape and a sumptuous range of amenities, you’ll be well-positioned to experience all the sights of stunning San Juan.
San Juan, the gateway to Puerto Rico, has welcomed countless global visitors throughout its centuries of existence. Internationally influenced, the city is today a bastion of fascinating cultural exploration and home to a dazzling array of luxury restaurants, shops, and clubs.
Day 4-6: Culebra and Vieques
Private Yacht Charter
Whilst Puerto Rico’s stunning mainland is home to an abundance of opportunities for luxurious relaxation in beautiful surroundings, to enable you to truly appreciate the country’s aquatic potential we’ll be sending you on a multi-day private yacht charter. Not only will this experience allow you to enjoy a range of watersports, but also visit two of Puerto Rico’s smaller island regions – Culebra and Vieques.
The islands of Culebra and Vieques, located just off Puerto Rico’s mainland, are two of the best places to enjoy the country’s unspoiled natural beauty. Whilst both are beautiful in their own right, Vieques is a truly remarkable destination, and home to the famous Mosquito Bioluminescent Bay, a nocturnally glowing lagoon that is sure to dazzle even the most seasoned traveler.
Day 7-9: Rio Grande
Perfectly located on an expansive former coconut farm and situated close to the El Yunque National Forest, The St. Regis Bahia Beach Resort is not only one of Puerto Rico’s best luxury resorts, but is also the ideal place to stay for exploring the island’s overgrown interior. With state-of-the-art cuisine, secluded beach access, and the world-famous Iridium Spa, guests staying at this St. Regis resort can expect nothing but the best.
Whilst Bahia Beach is home to some of Puerto Rico’s most fabulous beaches, the area is also well positioned to act as a luxurious base from which to explore the rugged majesty of the island’s expansive interior. From Bahia Beach, you’ll be able to venture into the lush terrain of El Yunque National Forest – the USA’s only protected tropical rainforest.
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.
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
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Frequently asked questions
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.
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.