Luxury Puerto Rico vacations

Puerto Rico Luxury Tours & Vacations & Holidays 2025 & 2026

Proudly LGBTQ+ Experts and Welcoming to All Travelers


Puerto Rico is the ideal destination for those seeking a blend of luxury and culture. Our luxury Puerto Rico vacations will let you experience the perfect balance of natural beauty, rich history, and indulgence.

Here at Out Of Office, we truly understand the world you live in, and the world you want to explore. Our attention to detail, exceptional service and deep understanding of both luxury travel and LGBTQ+ travel make us a fantastic choice for those looking for a travel experience where exclusivity meets inclusivity.

Why is Puerto Rico a popular luxury travel destination?

? Don't forget that all of our itineraries are totally customized and so this is just an idea of what we can build for you.

This picturesque Caribbean paradise evolved from a blend of Spanish, Taino Indian, and African influences, offering visitors stunning beaches, rolling green rainforests, and majestic mountains.

For those planning luxury trips to Puerto Rico, you’ll discover a lively melting pot of cultures and vibrant local communities, each with its unique charm.

Whether you’re embarking on luxury Puerto Rico travel to explore its palm-lined towns or to savor the island’s rich cultural heritage, there is always something new to uncover. Although small, Puerto Rico’s diversity is vast, providing a multitude of experiences throughout the island.

Nature lovers can hike lush mountain trails, pass gushing waterfalls, and explore exotic flora and fauna under the forest canopies. Puerto Rico’s impressive cave systems, rivers, and coral reefs are perfect for caving, kayaking, snorkeling, and diving expeditions, offering stunning ecological vistas. And with a luxury Puerto Rico group trip, travelers can indulge in these natural wonders together, guided by expert itineraries.

The culinary scene is unforgettable on the island, from world-renowned rum to spit-roasted pork and the birthplace of the piña colada. After a day of exploring, you can retreat to Puerto Rico’s luxurious resorts, where five-star service, private beaches, and world-class amenities await. Whether you seek adventure or relaxation, Puerto Rico offers a luxurious, unforgettable escape.


More Trips in Puerto Rico

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Luxury Puerto Rico
Luxury Puerto Rico

Tailor-Made

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...

Puerto Rico Culinary Tour
Puerto Rico Culinary Tour

Tailor-Made

Shaped by a rich tapestry of global influences including African, Spanish, and Taino Indian flavours, Puerto Rico’s culinary landscape offers a truly unique and unforgettable experience. From traditional delights like mofongo and arroz con gandules to innovative interpretations of Caribbean...

Miami and Puerto Rico
Miami and Puerto Rico

Tailor-Made

Experience 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...

Peter. S

“I'd never considered Puerto Rico to be a queer travel destination, but Out Of Office opened my eyes to its incredible vibrancy.”

Top rated luxury travel agency

Rueben. O

“We spent a week in Puerto Rico with Out Of Office, and loved every moment. ”

Top rated luxury travel agency

Rian. J

“My wife and I had always dreamt of going to Puerto Rico, and our Out Of Office trip was beyond our wildest dreams.”

Top rated luxury travel agency

Our Experts

Maria Gardner

Maria Gardner

Luxury Travel Expert

"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. "

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Dionne Charles

Dionne Charles

Luxury Travel Expert

"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. "

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Featured Experiences in Puerto Rico

Old San Juan
Old San Juan

With tiny streets lined with colorful properties adorned with flowers and intricate details, Old San Juan offers a glimpse into Puerto Rico’s colorful past and bears the signatures of the millions who have passed through this globally influenced city. The...

El Yunque National Forest
El Yunque National Forest

With cloud-touching palm trees and rushing white waterways, the El Yunque National Forest is a pristine example of Puerto Rico’s ecological diversity. Here you can take part in a host of outdoor pursuits, or simply relax in some of the...

Mosquito Bioluminescent Bay
Mosquito Bioluminescent Bay

Bioluminescence is a natural phenomenon that appears to be more akin to the dance of an alien lifeform than the simple biological functioning of microscopic organisms. Mosquito Bay is one of the best places in the entire world to observe...

Travel Information for Puerto Rico

General Information


Whether you’re looking for unrestricted five-star relaxation or the chance to enjoy some of Puerto Rico’s high-octane adventure experiences, regardless of your tastes you’re guaranteed a memorable time in stunning Puerto Rico.

Puerto Rico’s southern region, home to eleven towns including Ponce and Salinas, is characterized by white sand beaches that touch the azure waters of the Caribbean Sea. With some of the island’s most awe-inspiring coastal landscapes, the south is the ideal place to enjoy watersports and outdoor activities in Puerto Rico.

The west of Puerto Rico is a paradise for those travelers seeking a decidedly slower pace of life. Here, the laid-back atmosphere, warm-sand beaches, and stunning sunsets will lull you into an unimaginable sense of detached relaxation. It’s also a favorite spot for surfers, with crowds flocking from around the world to try their luck on an exhilarating collection of world-famous waves.

Puerto Rico’s capital San Juan forms part of the island’s Metro region – home to seven distinctive towns and the best place to enjoy LGBTQ+ nightlife as well as many of the island’s top restaurants and eateries.

Puerto Rico LGBTQ+ Rights


LGBTQ+ individuals in Puerto Rico enjoy legal protections that are in many ways similar to those of their heterosexual counterparts. As a U.S. territory, Puerto Rico has made significant advancements in LGBTQ+ rights over the years, reflecting broader trends toward social progress and inclusion. Same-sex marriage has been legally recognized since 2015, following the landmark U.S. Supreme Court decision, and the island has robust anti-discrimination laws that protect individuals based on sexual orientation and gender identity in areas such as employment, housing, and public accommodations.

These legal protections have been bolstered by efforts to raise awareness around LGBTQ+ issues. Public education campaigns and community outreach have played a pivotal role in breaking down the barriers and taboos surrounding LGBTQ+ relationships, helping to change public perceptions. Local LGBTQ+ advocacy groups have been instrumental in fostering a more inclusive environment, working to challenge stereotypes and promote acceptance across the island.

Puerto Rico is home to a vibrant LGBTQ+ community, celebrated through events like San Juan Pride and the Puerto Rico Queer Film Festival, both of which highlight the growing cultural appreciation for diversity. Cities like San Juan offer a generally welcoming atmosphere, with inclusive nightlife, queer-friendly accommodations, and a visible LGBTQ+ presence providing a sense of safety and belonging.

However, while progress is evident in urban areas, challenges remain in rural parts of the island, where traditional views can still dominate. Despite these hurdles, Puerto Rico continues to demonstrate a strong commitment to creating a more inclusive and equitable society, making it an increasingly attractive destination for LGBTQ+ travelers seeking a safe and supportive environment.

Things To Do In Puerto Rico

Mosquito Bay

The waters of Mosquito Bay on Vieques Island, Puerto Rico, light up like a starry night thanks to the natural bioluminescent organisms living in the bay. This unique phenomenon creates vivid displays of color that enchant visitors and is sure to create lasting memories for anyone lucky enough to see it.

Old San Juan

Old San Juan is a colorful section of Puerto Rico’s capital city, proudly displaying over 500 years of history. This historic district is defined by its cobblestone streets, bustling plazas, and pastel-colored buildings, reflecting both Spanish colonial and modern influences. It serves as a reminder of Puerto Rican culture and tradition, drawing in tourists looking to explore the old-world charm that has been so carefully preserved.

El Yunque National Forest

El Yunque National Forest is a must-see for anyone lucky enough to visit or live in Puerto Rico. It’s an absolutely stunning natural paradise situated in the northeast, boasting lush tropical rainforests, towering waterfalls, and a spectacular array of wildlife. Whether you’re looking for a thrilling adventure or simply longing to be surrounded by nature, El Yunque won’t disappoint.

Cuisine in Puerto Rico

If you’re looking to tantalize your taste buds while in Puerto Rico, you’ve come to the right place. Rich in flavourful and diverse traditional foods, from mofongo and lechon asado to tropical fritters (alcapurrias) and empanadillas – Puerto Rico has something for everyone. Check out some of its local eateries, or go on a food tour where you can sample all the best fare this beautiful island has to offer.

San Juan

San Juan, the exciting capital of Puerto Rico, features a beautiful blend of modern convenience and classic colonial allure. With marvelous sandy beaches, exquisite dining options and a unique cultural legacy, San Juan is an ideal getaway spot for those seeking an unparalleled Caribbean journey.

Amongst the must-see sights and attractions of San Juan is the old district – Old San Juan. Home to a range of historical structures, visitors flock to take in the beauty of monuments such as El Morro fortress, San Cristobal castle, and the Cathedral of San Juan Bautista.

The city of San Juan is a paradise for foodies. Here, you’ll find all sorts of delicacies and flavors that will tantalize your taste buds. From classic Puerto Rican cooking to international cuisine, there’s something here to satisfy every palate. Don’t miss out on having some classic dishes like lechon (roast pork) or arroz con gandules (rice with pigeon peas).

Central Mountains

If you’re looking for an off-the-beaten-path experience in Puerto Rico, the Central Mountains are a great option. They provide a unique, peaceful atmosphere, and offer beautiful views and countless opportunities for exploration. Visitors will encounter lush green forests, winding rivers, cascading waterfalls, and picturesque towns tucked away in the rolling hills.

In the Central Mountains awaits an oasis of relaxation: the Baño de Oro hot springs. Located in Coamo, these therapeutic springs are naturally filled with mineral-rich water and surrounded by lush, rolling hills. Many people come here to soak in the natural warmth of the water and unwind while taking in the beautiful scenery.

The El Yunque National Forest, located in central Puerto Rico, is an incredible destination for nature lovers. It’s the only tropical rainforest in the US National Forest system and boasts an abundance of lush vegetation and wildlife that visitors can explore while hiking through the area. The forest is also home to several waterfalls, which have stunning views from the summit, making it a popular spot for outdoor activities.

Culebra and Vieques

Culebra, located off the coast of Puerto Rico, is a small island paradise boasting breathtaking beaches and an abundance of underwater activities. Snorkelers and divers flock to this spot for its stunningly clear waters and array of tropical fish. Those looking for a tranquil beach vacation won’t need to look further than Culebra.

Vieques is another awe-inspiring island situated to the east of Puerto Rico. Home to a plethora of beaches, including Sun Bay Beach, Media Luna Beach, and Black Sand Beach, it’s a mecca for nature lovers. Moreover, its traditional culture is rich with stories and legends while its mystical nocturnal aquatic life emits a blue glow that can’t be found anywhere else in the world

A trip to Vieques, Puerto Rico, isn’t complete without a guided kayak tour of the bioluminescent bay – one of the island’s most remarkable attractions. The startling display is created by small organisms in the water that emit a glowing light when they are disturbed. Glide along the luminescent waters and witness a truly magical show.

Weather in Puerto Rico


  • January

    20°C - 30°C

    Puerto Rico's weather in January is warm and pleasant, with temperatures generally hovering around comfortable levels.

  • February

    20°C - 30°C

    February is a mild month in Puerto Rico, offering generally warm weather and occasional showers.

  • March

    20°C - 30°C

    In March, Puerto Rico experiences moderate heat, marking the beginning of the spring season.

  • April

    25°C - 30°C

    In April, Puerto Rico experiences moderately hot weather, typical of spring months.

  • May

    25°C - 30°C

    In Puerto Rico, the month of May is typically warm. The most common type of weather you'll find during this time of year is sunny days mixed with occasional periods of light rain and humidity.

  • June

    25°C - 35°C

    Puerto Rico in June is warm, making it the perfect time to visit the island.

  • July

    25°C - 35°C

    July in Puerto Rico is characterized by hot and humid weather.

  • August

    25°C - 35°C

    August in Puerto Rico is usually warm. Humidity levels are quite high, making it feel even hotter than it really is.

  • September

    25°C - 30°C

    Puerto Rico in September experiences warm temperatures with hot days and mild nights.

  • October

    20°C - 30°C

    Puerto Rico in October enjoys warm weather, making it a pleasant time for visitors to explore the island.

  • November

    20°C - 30°C

    Puerto Rico in November enjoys a moderate warm climate, making it the perfect month for taking in the beauty of this Caribbean island.

  • December

    20°C - 30°C

    December in Puerto Rico typically brings warm weather with the days slowly becoming cooler as it progresses into winter.

Getting to Puerto Rico


If you’re looking for a fast and convenient way to get to Puerto Rico, flying is the way to go. You can find flights from most cities in the United States and Canada, with some major airports offering direct flights. Once you’ve arrived, you’ll find two main airports – Luis Muñoz Marín International Airport (SJU) in San Juan and Rafael Hernández Airport (BQN) in Aguadilla – that are served by several airlines, including American Airlines, Delta, United, and Southwest.

Once you arrive at the airport, you can take a taxi, bus, or rental car to your destination. Taxis are available at the airport but can be costly. Taking the bus is more affordable but can often be crowded and slow. Alternatively, if you want more independence and flexibility, renting a car might be a better option. However, just bear in mind that driving in Puerto Rico may pose some challenges due to its narrow and winding roads.

Want to get to Puerto Rico but don’t want to fly? Consider a cruise. There are several cruise lines that offer trips to the island, with Carnival, Royal Caribbean, and Norwegian among the most popular. You’ll find two major ports on the island: San Juan Port and Port of the Americas.

From the blog

The Best Things to do in Puerto Rico
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...

The Best Gay-Friendly Hotels in the Caribbean
The Best Gay-Friendly Hotels in the Caribbean

The Caribbean is a dream holiday destination 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...

Puerto Rico vs. Barbados - which is better?
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...

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