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Top Holidays
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Beautiful beaches and
Beautiful beaches and

Puerto Rico Holidays

The beautiful island of Puerto Rico is part of an archipelago in the Caribbean Sea and is, in fact, a territory of the United States. Locals are American citizens but proudly refer to themselves as Boricuas, and embody an intoxicating culture with their food, architecture, and identity infused by Spanish, African, and Taíno traditions.

Beaches are in abundance here and there are more than 300 to explore over 270 miles of striking coastline, including the renowned Flamenco Beach in Culebra, with its toasty, white sand and glittering aquamarine water. The island’s diverse topography means that you’ll discover large expanses of pristine white sands with excellent water sports activities, as well as quiet, secluded coves for pure beach-bumming in the sunshine.

Puerto Rico comprises six distinct regions, all begging to be explored, and as the island is so small it can be driven around in a matter of hours. From the energy of the Metro region and its vibrant capital of San Juan to the laid-back surfer vibes of the West region with its glorious sunsets and excellent waves—every day promises a new adventure.

There is so much to discover in this beautiful destination, but where to start? Walk the cobbled and colourful streets of Old San Juan, discover lush natural wonders at El Yunque Rainforest or enjoy sampling the local flavours on a rum tasting tour or mixology class at Casa BACARDÍ—yes, that BACARDÍ—and discover the magic behind the production of the world’s most popular rum.

Food and drink are a passion of Boricuas, and your trip here won’t be complete until you try some of its most popular dishes like mofongo, made with deep-fried green plantains, and lechón asado, a delicately spit-roasted pork dish. Puerto Rico is also the birthplace of the piña colada—so, bottoms up!
The beautiful island of Puerto Rico is part of an archipelago in the Caribbean Sea and is, in fact, a territory of the United States. Locals are American citizens but proudly refer to themselves as Boricuas, and embody an intoxicating culture with their food, architecture, and identity infused by Spanish, African, and Taíno traditions.

Beaches are in abundance here and there are more than 300 to explore over 270 miles of striking coastline, including the renowned Flamenco Beach in Culebra, with its toasty, white sand and glittering aquamarine water. The island’s diverse topography means that you’ll discover large expanses of pristine white sands with excellent water sports activities, as well as quiet, secluded coves for pure beach-bumming in the sunshine.

Puerto Rico comprises six distinct regions, all begging to be explored, and as the island is so small it can be driven around in a matter of hours. From the energy of the Metro region and its vibrant capital of San Juan to the laid-back surfer vibes of the West region with its glorious sunsets and excellent waves—every day promises a new adventure.

There is so much to discover in this beautiful destination, but where to start? Walk the cobbled and colourful streets of Old San Juan, discover lush natural wonders at El Yunque Rainforest or enjoy sampling the local flavours on a rum tasting tour or mixology class at Casa BACARDÍ—yes, that BACARDÍ—and discover the magic behind the production of the world’s most popular rum.

Food and drink are a passion of Boricuas, and your trip here won’t be complete until you try some of its most popular dishes like mofongo, made with deep-fried green plantains, and lechón asado, a delicately spit-roasted pork dish. Puerto Rico is also the birthplace of the piña colada—so, bottoms up!
The beautiful island of Puerto Rico is part of an archipelago in the Caribbean Sea and is, in fact, a territory of the United States. Locals are American citizens but proudly refer to themselves as Boricuas, and embody an intoxicating culture with their food, architecture, and identity infused by Spanish, African, and Taíno traditions.

Beaches are in abundance here and there are more than 300 to explore over 270 miles of striking coastline, including the renowned Flamenco Beach in Culebra, with its toasty, white sand and glittering aquamarine water. The island’s diverse topography means that you’ll discover large expanses of pristine white sands with excellent water sports activities, as well as quiet, secluded coves for pure beach-bumming in the sunshine.

Puerto Rico comprises six distinct regions, all begging to be explored, and as the island is so small it can be driven around in a matter of hours. From the energy of the Metro region and its vibrant capital of San Juan to the laid-back surfer vibes of the West region with its glorious sunsets and excellent waves—every day promises a new adventure.

There is so much to discover in this beautiful destination, but where to start? Walk the cobbled and colourful streets of Old San Juan, discover lush natural wonders at El Yunque Rainforest or enjoy sampling the local flavours on a rum tasting tour or mixology class at Casa BACARDÍ—yes, that BACARDÍ—and discover the magic behind the production of the world’s most popular rum.

Food and drink are a passion of Boricuas, and your trip here won’t be complete until you try some of its most popular dishes like mofongo, made with deep-fried green plantains, and lechón asado, a delicately spit-roasted pork dish. Puerto Rico is also the birthplace of the piña colada—so, bottoms up!
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Stunning
Beaches

Relax on impeccable sands, frolic in crystal-clear waters, and bask under the glorious sunshine for the ultimate island escape. Every day is a beach day in Puerto Rico!

Stunning Beaches

Relax on impeccable sands, frolic in crystal-clear waters, and bask under the glorious sunshine for the ultimate island escape. Every day is a beach day in Puerto Rico!

Historical
Landmarks

500 years of history and a vibrant mix of cultures make Puerto Rico the fascinating place it is today. Explore museums, forts, and religious buildings for a deep dive into the island’s heart and soul.

Historical Landmarks

500 years of history and a vibrant mix of cultures make Puerto Rico the fascinating place it is today. Explore museums, forts, and religious buildings for a deep dive into the island’s heart and soul.

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Culinary
Traditions

Inspired by Spanish, African, and Taíno cuisine, Puerto Rican food is varied and tasty! Savour spicy, succulent meats and deep-fried comfort foods, washed down with a refreshing beer or rum cocktail.

Culinary Traditions

Inspired by Spanish, African, and Taíno cuisine, Puerto Rican food is varied and tasty! Savour spicy, succulent meats and deep-fried comfort foods, washed down with a refreshing beer or rum cocktail.

Inspired?
Start planning your
next trip today

Our expert team of personal travel managers are ready to craft your perfect journey. From business trips to luxury leisure holidays, simply put your pin in the map, and we’ll make it happen.

Luxury Puerto Rico Hotels

Luxury Puerto Rico Hotels

Dorado Beach, A Ritz-Carlton Reserve

Dorado , Puerto Rico

As a Ritz-Carlton Reserve, Dorado Beach is where exclusive five-star luxury meets Caribbean charm. Bask in oceanfront peacefulness, dine on world-class cuisine, and experience a quieter way of island life in Puerto Rico’s rainforest paradise.

As a Ritz-Carlton Reserve, Dorado Beach is where exclusive five-star luxury meets Caribbean charm. Bask in oceanfront peacefulness, dine on world-class cuisine, and experience a quieter way of island life in Puerto Rico’s rainforest paradise.

As a Ritz-Carlton Reserve, Dorado Beach is where exclusive five-star luxury meets Caribbean charm. Bask in oceanfront peacefulness, dine on world-class cuisine, and experience a quieter way of island life in Puerto Rico’s rainforest paradise.

The St. Regis Bahai Beach Resort, Puerto Rico

Rio Grande, Puerto Rico

A paradise on Puerto Rico’s northern coast, this resort blends the country’s tropical beauty with five-star luxury living. Enjoy stunning surrounding gardens, oceanfront views, and endless activities for luxury–seekers and adventurous nature lovers.

A paradise on Puerto Rico’s northern coast, this resort blends the country’s tropical beauty with five-star luxury living. Enjoy stunning surrounding gardens, oceanfront views, and endless activities for luxury–seekers and adventurous nature lovers.

A paradise on Puerto Rico’s northern coast, this resort blends the country’s tropical beauty with five-star luxury living. Enjoy stunning surrounding gardens, oceanfront views, and endless activities for luxury–seekers and adventurous nature lovers.

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The Finishing Touches

You've chosen your accommodation, booked your flights, so what's next?

Our personal experience team are here to help you holiday your way, from reservations to unique recommendations
Our personal experience team are here to help you holiday your way, from reservations to unique recommendations
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Winged Boots Interviews: Claire Baker, Luxury Concierge for Winged Boots

From reservations to romantic proposals, see how our dedicated personal experience team can add some extra sparkle to an already incredible travel experience.

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How Winged Boots' luxury travel concierge can take your holiday to new heights

From bookings to expert advice, discover how our luxury travel concierge service can create a bespoke itinerary fit for royalty.

Puerto Rico in a Nutshell

Flamenco Beach earns its place as one of the world’s top beaches, with cerulean waters and cloud-like sands edged by arching palm trees, it’s a picture-perfect location for both swimming and sunbathing.

If you’re in search of an active beach stay, head for the west coast where the waves are gnarly, and the surf is ideal. The pretty town of Rincón boasts an array of stunning beaches that are great for both experienced and beginner surfers such as María, Sandy, Domes, and Tres Palmas.

The popular Crash Boat Beach—located in Aguadilla on the island’s northwest shore—has plenty to keep you occupied, with great snorkelling, scuba diving, and surfing opportunities for all levels, as well as a range of water sports like jet-skiing.

For a truly magical, one-of-a-kind experience, take a trip to one of Puerto Rico’s ghostly bioluminescent bays. Mosquito Bay is officially the world’s brightest and is set on Vieques Island, which is accessible via a small plane or ferry. Hire a glass-bottom kayak and float along the bay, and when you splash the water, you’ll be mesmerised by the neon blue-green glow beneath you.

Back on dry land, make time to explore the 500-year history of Old San Juan (Viejo San Juan), the oldest European-founded city in the Americas. This gorgeous historical town comprises colonial buildings and iconic ancient sites, with charming cobblestoned streets that give it a vintage movie feel. Stroll around cultural landmarks like Castillo San Felipe del Morro and Castillo San Cristóbal, two important Spanish citadels, and see the grand Catedral de San Juan Bautista for a glimpse into its religious past.

Puerto Rican cuisine derives from lots of different flavours and methods in Spanish, African, and native Taino cookery, making its dishes unique and memorable. Eating out in Puerto Rico is a fabulous experience, and whether it’s in a fine dining establishment or a rustic street food kiosk by the beach, you’re guaranteed a taste sensation.

Marmalade restaurant in San Juan offers a contemporary and exciting fine dining experience with an eclectic fusion of French, Caribbean, and Spanish cuisine. With a focus on organic produce and sustainability, Marmalade also boasts an excellent bar for those cheeky post-dinner beverages.

A hugely popular way to discover Puerto Rico’s thriving culinary scene is to take a fun chinchorro tour along the coast, either by car or bus. Head for the lovely coastal area of Piñones, just a thirty-minute journey from San Juan, for a day out like no other. This truly local dining experience is the art of hopping from one food truck to the next and eating and drinking your way through classic island staples such as fritters, sweet and smoky grilled meats, skewered kebabs, fluffy rice, not to mention delicious cocktails and beer. It’s the Puerto Rican equivalent of a bar crawl and an experience not to be missed!
Flamenco Beach earns its place as one of the world’s top beaches, with cerulean waters and cloud-like sands edged by arching palm trees, it’s a picture-perfect location for both swimming and sunbathing.

If you’re in search of an active beach stay, head for the west coast where the waves are gnarly, and the surf is ideal. The pretty town of Rincón boasts an array of stunning beaches that are great for both experienced and beginner surfers such as María, Sandy, Domes, and Tres Palmas.

The popular Crash Boat Beach—located in Aguadilla on the island’s northwest shore—has plenty to keep you occupied, with great snorkelling, scuba diving, and surfing opportunities for all levels, as well as a range of water sports like jet-skiing.

For a truly magical, one-of-a-kind experience, take a trip to one of Puerto Rico’s ghostly bioluminescent bays. Mosquito Bay is officially the world’s brightest and is set on Vieques Island, which is accessible via a small plane or ferry. Hire a glass-bottom kayak and float along the bay, and when you splash the water, you’ll be mesmerised by the neon blue-green glow beneath you.

Back on dry land, make time to explore the 500-year history of Old San Juan (Viejo San Juan), the oldest European-founded city in the Americas. This gorgeous historical town comprises colonial buildings and iconic ancient sites, with charming cobblestoned streets that give it a vintage movie feel. Stroll around cultural landmarks like Castillo San Felipe del Morro and Castillo San Cristóbal, two important Spanish citadels, and see the grand Catedral de San Juan Bautista for a glimpse into its religious past.

Puerto Rican cuisine derives from lots of different flavours and methods in Spanish, African, and native Taino cookery, making its dishes unique and memorable. Eating out in Puerto Rico is a fabulous experience, and whether it’s in a fine dining establishment or a rustic street food kiosk by the beach, you’re guaranteed a taste sensation.

Marmalade restaurant in San Juan offers a contemporary and exciting fine dining experience with an eclectic fusion of French, Caribbean, and Spanish cuisine. With a focus on organic produce and sustainability, Marmalade also boasts an excellent bar for those cheeky post-dinner beverages.

A hugely popular way to discover Puerto Rico’s thriving culinary scene is to take a fun chinchorro tour along the coast, either by car or bus. Head for the lovely coastal area of Piñones, just a thirty-minute journey from San Juan, for a day out like no other. This truly local dining experience is the art of hopping from one food truck to the next and eating and drinking your way through classic island staples such as fritters, sweet and smoky grilled meats, skewered kebabs, fluffy rice, not to mention delicious cocktails and beer. It’s the Puerto Rican equivalent of a bar crawl and an experience not to be missed!
Flamenco Beach earns its place as one of the world’s top beaches, with cerulean waters and cloud-like sands edged by arching palm trees, it’s a picture-perfect location for both swimming and sunbathing.

If you’re in search of an active beach stay, head for the west coast where the waves are gnarly, and the surf is ideal. The pretty town of Rincón boasts an array of stunning beaches that are great for both experienced and beginner surfers such as María, Sandy, Domes, and Tres Palmas.

The popular Crash Boat Beach—located in Aguadilla on the island’s northwest shore—has plenty to keep you occupied, with great snorkelling, scuba diving, and surfing opportunities for all levels, as well as a range of water sports like jet-skiing.

For a truly magical, one-of-a-kind experience, take a trip to one of Puerto Rico’s ghostly bioluminescent bays. Mosquito Bay is officially the world’s brightest and is set on Vieques Island, which is accessible via a small plane or ferry. Hire a glass-bottom kayak and float along the bay, and when you splash the water, you’ll be mesmerised by the neon blue-green glow beneath you.

Back on dry land, make time to explore the 500-year history of Old San Juan (Viejo San Juan), the oldest European-founded city in the Americas. This gorgeous historical town comprises colonial buildings and iconic ancient sites, with charming cobblestoned streets that give it a vintage movie feel. Stroll around cultural landmarks like Castillo San Felipe del Morro and Castillo San Cristóbal, two important Spanish citadels, and see the grand Catedral de San Juan Bautista for a glimpse into its religious past.

Puerto Rican cuisine derives from lots of different flavours and methods in Spanish, African, and native Taino cookery, making its dishes unique and memorable. Eating out in Puerto Rico is a fabulous experience, and whether it’s in a fine dining establishment or a rustic street food kiosk by the beach, you’re guaranteed a taste sensation.

Marmalade restaurant in San Juan offers a contemporary and exciting fine dining experience with an eclectic fusion of French, Caribbean, and Spanish cuisine. With a focus on organic produce and sustainability, Marmalade also boasts an excellent bar for those cheeky post-dinner beverages.

A hugely popular way to discover Puerto Rico’s thriving culinary scene is to take a fun chinchorro tour along the coast, either by car or bus. Head for the lovely coastal area of Piñones, just a thirty-minute journey from San Juan, for a day out like no other. This truly local dining experience is the art of hopping from one food truck to the next and eating and drinking your way through classic island staples such as fritters, sweet and smoky grilled meats, skewered kebabs, fluffy rice, not to mention delicious cocktails and beer. It’s the Puerto Rican equivalent of a bar crawl and an experience not to be missed!

frequently asked questions

Between December and April is the best time—but also the most expensive—to visit in terms of weather but it’s also a time for festivals and celebration in Puerto Rico, where the whole island comes alive in colour, music, food, and art. The average daily temperature hovers between 21-26°C, ensuring that beach days are comfortable.

Hurricane season hits its peak in September and prices are predictably cheaper, while the shoulder months of May and November are less crowded with pleasant enough weather to swim and explore.
Flights are frequent from several UK airports to San Juan, including London, Manchester, Edinburgh, Birmingham and Belfast. They are usually indirect and will make a quick stop via New York or Atlanta.
As Puerto Rico is a part of the USA, all travellers from the UK must apply for an Electronic System for Travel Authorisation (ESTA) visa waiver prior to arrival.
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Inspired?
Start planning your
next trip today

Our expert team of personal travel managers are ready to craft your perfect journey. From business trips to luxury leisure holidays, simply put your pin in the map, and we’ll make it happen.