Luxury Puerto Rico vacations

Puerto Rico

A picture-perfect Caribbean paradise evolved from a blend of Spanish, Taino Indian, and African influences, Puerto Rico is a charming island commonwealth fringed with sandy beaches and boasting a luscious landscape of rolling green rainforest and sky-scraping mountains. Puerto Rico is a destination that truly does have something to offer every traveller.

At a glance

? 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.

A melting pot of cultures and communities, Puerto Rico is a lively and colorful destination that bears the signatures of the thousands of individuals who have called the island home throughout the centuries. Although small in size, and easily drivable in around six hours, the range of local cultures in Puerto Rico is astounding, and travellers will find diverse experiences to explore throughout its palm-lined towns and cities.

Few places on earth have the same varied history as Puerto Rico, having seen countless periods of occupation and colonization throughout the centuries. From the original Taino inhabitants who first farmed Puerto Rico’s land to the infamous arrival of the Spanish in 1493, each group that spent time on the island has left their distinctive mark on the present-day culture of Puerto Rico.

The flavors of Puerto Rico’s mouth-watering culinary scene will stay with you well after you leave this mesmerizing tropical island. The destination boasts a range of culinary headliners, ranging from world-leading rum varieties and spit-roasted pork to the pina colada- a drink that began its life on the laid-back spill of Puerto Rico.


More Trips in Puerto Rico

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Puerto Rico Culinary Tour
Puerto Rico Culinary Tour

Tailor-Made

Floating in the heart of the Caribbean Sea, Puerto Rico is a culinary paradise that promises a rich and diverse range of textures, flavors, and aromas. Here you can enjoy traditional dishes such as mofongo and arroz con gandules or...

Miami and Puerto Rico
Miami and Puerto Rico

Tailor-Made

Miami and Puerto Rico are two of the USA’s most popular luxury travel destinations, both boasting a range of luxury properties as well as breathtaking coastal scenery. This twin-center itinerary has been designed to showcase the highlights of both destinations...

Luxury Puerto Rico
Luxury Puerto Rico

Tailor-Made

With its world-renowned stretches of white-sand beach, rich cultural heritage and too-many five-star resorts to count, Puerto Rico is one of the Caribbean’s best destinations for a truly luxurious island getaway. This unique unincorporated U.S. territory is not only home...

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

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...

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...

Travel 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 travellers 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.

LGBTQ+ people in Puerto Rico enjoy almost the same legal protections as their heterosexual counterparts, and general issues of identity and equality are becoming increasingly popular talking points. This has led to a softening of taboos around same-sex relationships and LGBTQ+ travellers can expect a safe and comfortable trip.

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 holiday 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 worldA 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.

  • 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.

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 Top Cultural Activities to Enjoy in Puerto Rico
The Top Cultural Activities to Enjoy in Puerto Rico

Salsa dancing Even if you have two left feet or have never danced before, something you have to do whilst in Puerto Rico is head to a salsa bar. Even if you don’t dance, just watching the locals perform is...

Our competition winners explore the wonders of Puerto Rico
Our competition winners explore the wonders of Puerto Rico

Our lucky competition winners James and Tomek are currently sipping cocktails and exploring the beautiful island of Puerto Rico. We’ve sent them to San Juan on an all expenses paid trip and it certainly looks like they are enjoying the...

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