Tailor-made Holiday · Puerto Rico
Timeless Puerto Rico: Culture, Coastlines and Canopies
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Every trip built from scratch around your dates, pace and preferences.
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At a glance
Step 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.
Discover the soulful rhythms of Puerto Rico’s rich heritage as you wander its colorful colonial streets, explore centuries-old fortresses, and taste the fusion of flavors that define its cuisine. In Vieques, serenity takes center stage. Lounge on pristine, secluded beaches or marvel at the glowing waters of the bioluminescent bay—a natural phenomenon that feels nothing short of magical.
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For adventurers, the lush canopies of El Yunque rainforest beckon. Here, cascading waterfalls, hidden trails, and an orchestra of nature provide moments of tranquility and awe. Journey further to Ponce, the cultural heart of the south, and Cabo Rojo, where dramatic cliffs and turquoise waters create a breathtaking setting for the final chapter of your trip.
In Cabo Rojo, you’ll find dramatic cliffs plunging into turquoise waters and a coastline untouched by time. Visit the iconic Los Morrillos Lighthouse, perched high above the sea, and soak in the sweeping views of sun-drenched beaches and shimmering salt flats. Whether savoring fresh seafood at a seaside café or basking in the golden glow of a Caribbean sunset, Cabo Rojo is a fitting conclusion to the trip of a lifetime.
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: Arrival in San Juan
Arrive in Puerto Rico’s lively capital, where a private transfer will take you to your luxury boutique hotel in Old San Juan. After settling in, take a leisurely evening walk through the historic streets, marveling at the colorful colonial buildings. Dinner at a fine-dining restaurant introduces you to the island’s vibrant culinary scene, where traditional Puerto Rican flavors are reimagined with modern flair.
Day 2: Discovering Old San Juan
Spend the day uncovering the historic charm of Old San Juan. A private guide will lead you through iconic landmarks like El Morro and Castillo San Cristóbal, where centuries of history come alive. Pause for lunch at a charming café before visiting local artisan shops. In the evening, enjoy a sunset cocktail on your hotel’s rooftop terrace, with views stretching over the Atlantic Ocean.
Day 3: El Yunque Rainforest Adventure
Venture into the lush greenery of El Yunque National Forest, the only tropical rainforest in the U.S. National Forest System. A private eco-tour will take you to cascading waterfalls and hidden pools, where you can swim and rejuvenate. Savor a gourmet picnic surrounded by nature before returning to your hotel in San Juan for an evening at leisure.
Day 4: Vieques Island
Travel by private ferry or flight to Vieques, an island paradise known for its tranquil beaches and bioluminescent bay. Check into a luxurious beachfront resort, where the serene surroundings set the tone for relaxation. Spend the afternoon lounging on pristine sands or exploring the nearby mangroves. Dinner at the resort features fresh, locally sourced seafood.
Day 5: Bioluminescent Bay Excursion
Enjoy a day at leisure, soaking in the beauty of Vieques’ secluded beaches. In the evening, embark on a magical kayaking tour of Mosquito Bay, the brightest bioluminescent bay in the world. Paddle through glowing waters under a starlit sky, a once-in-a-lifetime experience that epitomizes the natural wonders of Puerto Rico.
Day 6: Discover Ponce
Journey back to the mainland and head south to Ponce, the “Pearl of the South.” Check into an elegant historic hotel in the city centre. Spend the day exploring Ponce’s cultural gems, including the Ponce Museum of Art and Parque de Bombas, a historic firehouse turned museum. Indulge in a sophisticated dinner at a local fine-dining restaurant.
Day 7: Escape to the Mountains
Take a scenic drive into Puerto Rico’s central highlands to Adjuntas, the island’s coffee capital. Visit a sustainable coffee plantation for a private tour and tasting, learning about Puerto Rico’s rich coffee culture. Enjoy lunch at a mountain lodge with panoramic views before returning to Ponce for an evening of relaxation.
Day 8: Cabo Rojo Awaits
Head west to Cabo Rojo, where dramatic cliffs, stunning beaches, and a picturesque lighthouse await. Spend the day at Playa Sucia, known for its turquoise waters and tranquil atmosphere. Visit the salt flats and lighthouse for breathtaking views before heading back to Ponce for a final evening of culinary delights.
Day 9: Farewell to Puerto Rico
Return to San Juan for your departure. Depending on your flight time, enjoy some last-minute shopping or a leisurely brunch in the city. A private transfer ensures a smooth journey to the airport, concluding your unforgettable Puerto Rican adventure.
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.
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.