Luxury Caribbean Holidays
One of the highlights of a luxury Caribbean holiday is the range of all-inclusive resorts, providing you with everything from gourmet dining and spa treatments to watersports and private excursions. These all-inclusive Caribbean holidays offer unmatched convenience, where everything is taken care of - allowing you to fully unwind and embrace the destination’s natural beauty. Whether you stay in private beachfront villas or overwater bungalows, you’ll enjoy exceptional service and access to a host of luxury amenities.
The Caribbean is also home to some of the most family-friendly Caribbean islands. Islands such as Jamaica, Barbados, and the Bahamas offer family-oriented resorts with kid’s clubs, family suites, and numerous activities that can keep children entertained while parents indulge in relaxing spa treatments or fine dining. Many of these resorts also offer educational and cultural experiences, such as local cooking classes or nature tours, ensuring your little ones not only have fun but also learn about the rich history and culture of the islands.
With its mix of relaxation, adventure, and cultural immersion, a Caribbean holiday is perfect for every type of traveller. Whether you want to explore vibrant island cultures, snorkel in vibrant coral reefs, or simply unwind with a cocktail by the beach, the Caribbean offers a unique blend of luxury and laid-back charm that promises an unforgettable vacation.
One of the highlights of a luxury Caribbean holiday is the range of all-inclusive resorts, providing you with everything from gourmet dining and spa treatments to watersports and private excursions. These all-inclusive Caribbean holidays offer unmatched convenience, where everything is taken care of - allowing you to fully unwind and embrace the destination’s natural beauty. Whether you stay in private beachfront villas or overwater bungalows, you’ll enjoy exceptional service and access to a host of luxury amenities.
The Caribbean is also home to some of the most family-friendly Caribbean islands. Islands such as Jamaica, Barbados, and the Bahamas offer family-oriented resorts with kid’s clubs, family suites, and numerous activities that can keep children entertained while parents indulge in relaxing spa treatments or fine dining. Many of these resorts also offer educational and cultural experiences, such as local cooking classes or nature tours, ensuring your little ones not only have fun but also learn about the rich history and culture of the islands.
With its mix of relaxation, adventure, and cultural immersion, a Caribbean holiday is perfect for every type of traveller. Whether you want to explore vibrant island cultures, snorkel in vibrant coral reefs, or simply unwind with a cocktail by the beach, the Caribbean offers a unique blend of luxury and laid-back charm that promises an unforgettable vacation.
One of the highlights of a luxury Caribbean holiday is the range of all-inclusive resorts, providing you with everything from gourmet dining and spa treatments to watersports and private excursions. These all-inclusive Caribbean holidays offer unmatched convenience, where everything is taken care of - allowing you to fully unwind and embrace the destination’s natural beauty. Whether you stay in private beachfront villas or overwater bungalows, you’ll enjoy exceptional service and access to a host of luxury amenities.
The Caribbean is also home to some of the most family-friendly Caribbean islands. Islands such as Jamaica, Barbados, and the Bahamas offer family-oriented resorts with kid’s clubs, family suites, and numerous activities that can keep children entertained while parents indulge in relaxing spa treatments or fine dining. Many of these resorts also offer educational and cultural experiences, such as local cooking classes or nature tours, ensuring your little ones not only have fun but also learn about the rich history and culture of the islands.
With its mix of relaxation, adventure, and cultural immersion, a Caribbean holiday is perfect for every type of traveller. Whether you want to explore vibrant island cultures, snorkel in vibrant coral reefs, or simply unwind with a cocktail by the beach, the Caribbean offers a unique blend of luxury and laid-back charm that promises an unforgettable vacation.
The Caribbean offers a barefoot holiday experience. Think soft reggae music playing, fresh fruits on the beach and a casual vibe where day blends into night, like the sun sets over the ocean.
Laid-back Luxury
The Caribbean offers a barefoot holiday experience. Think soft reggae music playing, fresh fruits on the beach and a casual vibe where day blends into night, like the sun sets over the ocean.
There’s so much to entertain all members of your clan from watersports and history to golf and spas. Why not book a private villa and bring Nan, Grandad and all the cousins along too?
Fun for the Family
There’s so much to entertain all members of your clan from watersports and history to golf and spas. Why not book a private villa and bring Nan, Grandad and all the cousins along too?
The inviting coast and its aquatic activities is a big draw, but the Caribbean is more than just beaches. Hike mountains, visit rum distilleries, discover historic towns and chase waterfalls in lush jungles.
More than Beaches
The inviting coast and its aquatic activities is a big draw, but the Caribbean is more than just beaches. Hike mountains, visit rum distilleries, discover historic towns and chase waterfalls in lush jungles.
Caribbean Holiday Destinations
Caribbean Holiday Destinations
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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.
START A WHATSAPP CHATLuxury Caribbean Hotels
Luxury Caribbean Hotels
Cap Juluca, A Belmond Hotel
Maundays Bay, Anguilla
Experience unparalleled luxury at Cap Juluca, A Belmond Hotel. Enjoy beachfront villas with private terraces, gourmet dining, a serene Guerlain Spa, and world-class amenities, all set against Anguilla's tropical landscapes.
Experience unparalleled luxury at Cap Juluca, A Belmond Hotel. Enjoy beachfront villas with private terraces, gourmet dining, a serene Guerlain Spa, and world-class amenities, all set against Anguilla's tropical landscapes.
Experience unparalleled luxury at Cap Juluca, A Belmond Hotel. Enjoy beachfront villas with private terraces, gourmet dining, a serene Guerlain Spa, and world-class amenities, all set against Anguilla's tropical landscapes.
Four Seasons Resort & Residences Anguilla
Barnes Bay, Anguilla
Perched on Anguilla’s pristine shores, this luxury retreat offers unparalleled oceanfront elegance. With world-class dining, serene pools, and bespoke experiences, it’s a place where relaxation meets sophistication, creating unforgettable moments.
Perched on Anguilla’s pristine shores, this luxury retreat offers unparalleled oceanfront elegance. With world-class dining, serene pools, and bespoke experiences, it’s a place where relaxation meets sophistication, creating unforgettable moments.
Perched on Anguilla’s pristine shores, this luxury retreat offers unparalleled oceanfront elegance. With world-class dining, serene pools, and bespoke experiences, it’s a place where relaxation meets sophistication, creating unforgettable moments.
Malliouhana
Meads Bay, Anguilla
Malliouhana, located on Anguilla's Meads Bay, is a luxurious Caribbean resort blending modern elegance with island charm. It offers beachfront accommodations, world-class dining, a serene spa, and vibrant activities for unforgettable getaways.
Malliouhana, located on Anguilla's Meads Bay, is a luxurious Caribbean resort blending modern elegance with island charm. It offers beachfront accommodations, world-class dining, a serene spa, and vibrant activities for unforgettable getaways.
Malliouhana, located on Anguilla's Meads Bay, is a luxurious Caribbean resort blending modern elegance with island charm. It offers beachfront accommodations, world-class dining, a serene spa, and vibrant activities for unforgettable getaways.
Carlisle Bay
Antigua, Caribbean
Laid back luxury and Caribbean charm exudes the renowned Carlisle Bay. This beachfront resort sits on the Antiguan shores and offers its guests an escape from the real world. Welcome to paradise.
Laid back luxury and Caribbean charm exudes the renowned Carlisle Bay. This beachfront resort sits on the Antiguan shores and offers its guests an escape from the real world. Welcome to paradise.
Laid back luxury and Caribbean charm exudes the renowned Carlisle Bay. This beachfront resort sits on the Antiguan shores and offers its guests an escape from the real world. Welcome to paradise.
Start Your Journey
Before you book your holiday to the Caribbean, discover more with these insightful reads and holiday ideas.
10 reasons to book with Winged Boots
You'll soon understand why we're a leading luxury travel specialist
Cheval Blanc St-Barth Isle De France
Cheval Blanc St-Barth is a luxurious, five-star resort in the Caribbean, offering stunning accommodation, world-class dining, a serene spa, and personalised services. The rooms, suites, bungalows and villas cater to all, from couples to families.
Jumby Bay Island
Jumby Bay Island is a luxurious private island resort off Antigua’s coast in the Caribbean. Known for its white sandy beaches, crystal-clear waters, and fully inclusive offering; expect a serene relaxation in a tropical paradise.
Sandy Lane
Sandy Lane is an institution on Barbados’ platinum coast. Enjoy unrivalled golf, delectable dining and a level of service that would put Buckingham Palace to shame. Ideal for couples, families and honeymooners… you won’t ever want to leave.
COMO Parrot Cay
Experience luxury on 1,000 acres of pure paradise with private beachfront villas, an award-winning spa, gourmet dining, and a wellness centre. Enjoy yoga, water sports, and serene nature trails on this exclusive private island retreat.
Rosewood Le Guanahani
Nestled on an 18-acre private peninsula in St. Barth, Rosewood Le Guanahani offers 66 vibrant accommodations, two beaches, two pools, a spa, fitness centre, and children's club, blending French-Caribbean charm with modern luxury.
Popular Tours
Cuba & Jamaica, 15 Days
Combine Cuba and Jamaica for fun (and rum) in the sun. Enjoy a vintage car city tour and Vinales Valley exploration in Cuba. Then, enjoy Jamaica’s Half Moon Hotel and a private Appleton Rum Estate tour.
Cuba & Montego Bay, 13 Days
Indulge in Caribbean bliss with a 12-night holiday in Cuba and Jamaica. Stay at Cuba's Paradisus Princesa del Mar Varadero and tour Havana in a vintage car, then relax at Jamaica’s Half Moon with a private Appleton Rum Estate tour.
Cuba & St. Lucia, 11 Days
Experience Caribbean luxury with stays at Gran Hotel Manzana Kempinski and Marigot Bay Resort. Enjoy a private Havana tour in a vintage car, followed by ultimate relaxation in St. Lucia.
Antigua, St. Lucia & Barbados, 15 Days
Embark on a two-week Caribbean odyssey. Enjoy Antigua's pristine beaches at Jumby Bay, rejuvenate at St. Lucia's Calabash Cove, and revel in the beauty of Barbados' Sandy Lane. Paradise awaits at every turn.
Grenada, St. James & Antigua, 15 Days
Embark on a 14-night island-hopping dream. Begin with five nights at Calabash Grenada’s luxurious suites, seafood dining, and serene spa. Continue to Barbados' Fairmont Royal Pavilion, then conclude in Antigua's opulent Blue Waters Resort & Spa.
Miami & Jamaica, 15 Days
Experience a thrilling 14-night adventure from Miami to Jamaica, including luxurious stays, a supercar drive, a private airboat tour in the Everglades, and a relaxing week at the Half Moon Hotel in paradise.
Las Vegas & Jamaica, 15 Days
Experience the best of both worlds with four nights at The Cosmopolitan Las Vegas, including a Grand Canyon helicopter trip and limousine Strip tour, followed by 10 nights of luxury at GoldenEye Jamaica with an Appleton Rum Estate experience.
Antigua & Anguilla, 11 Days
Experience paradise with a 10-night Caribbean getaway to Antigua and Anguilla, featuring luxurious stays at Carlisle Bay and Cap Juluca, exquisite local cuisine, a powerboat tour, and exciting watersports amidst breathtaking oceanfront settings.
Bahamas & Turks & Caicos, 15 Days
Enjoy a two-week Caribbean escape to The Bahamas and Turks & Caicos, thrilling water park access, an excursion to Rose Island's famous pigs, and ultimate relaxation at COMO Parrot Cay's private island retreat.
Grenada & St Lucia, 15 Days
Combine two of the best islands in the Caribbean on this getaway. Explore the highlights of Grenada including chocolate making and a rum distillery tour before jetting to St. Lucia where a land and sea trip awaits.
Grenada & St. Lucia, 15 Days
Immerse yourself in Caribbean luxury with a 14-night retreat to Grenada's Spice Island Beach Resort and St. Lucia's Sugar Beach, A Viceroy Resort. Exquisite cuisine, stunning beaches, and endless activities await.
St. Lucia & Antigua, 15 Days
Experience 14 nights of paradise in St. Lucia and Antigua. Begin with seven nights at St. Lucia’s Calabash Cove Resort & Spa, then enjoy seven nights at Antigua’s luxurious Hermitage Bay, offering stunning views and ultimate relaxation.
Maundays Bay & St. Maarten, 9 Days
Begin on Anguilla’s platinum sands with barefoot beach rides and reef-fringed sails, then hop to St. Martin for French-accented island charm, Champagne sunsets and wild encounters in the shimmering shallows of the Caribbean Sea.
The Caribbean in a Nutshell
The gem in the Caribbean crown, Barbados is one of the most popular island destinations and with one step on the sands, you’ll understand why. Home to stunning resorts with a whole host of facilities, it’ll be so tempting to stay put but don’t give in. Put on your walking shoes and see what beautiful Barbados beholds.
Feel like a local in Barbados as you head down to Oistin’s Fish Fry for some Friday night fun or explore the natural wonder of Harrison’s Cave. Or, if you just want simple relaxation, lounge on one of the sandy beaches with a tropical cocktail to match the light tropical breeze. This kind of bliss can’t be compared.
St. Lucia
Cameras at the ready! St. Lucia is truly stunning, boasting picturesque views everywhere you turn. But, if beach views and mountaintop vistas aren’t enough for you, take an Instagram snap of Sulphur Springs, the world’s only ‘drive-in’ volcano. Once guests get their share of fiery views, they can enjoy a mud bath at the springs, said to have healing properties so you can turn your very own body into a beautiful natural wonder.
Pigeon Island is one of the most popular island destinations, worth the 90-minute drive from the airport. Panoramic vistas brimming with history can be taken in while exploring the relics and ruins of Fort Rodney before stopping for a bite to eat. On-site restaurants Jambe de Bois and The Captain’s Cellar Bar & Restaurant both offer great island cuisine for a delicious lunch or dinner in the sun.
The Bahamas
Paradise never looked so good. Made up of more than 700 islands and cays, it’s incredibly easy to get lost in The Bahamas. But, find your bearings for a visit to Aquaventure Waterpark. This is a great destination for the whole family with plenty of slides and pools to provide hours of entertainment. Less than an hour from Nassau, the park can be found on Paradise Island where you’ll also find the commanding Atlantis resort.
No trip to The Bahamas is complete without a visit to Pig Beach. Watch the Instagram likes roll in as you take snaps of swimming with these magnificent creatures, totally worth every minute of the three hour boat ride from Grand Exuma.
The gem in the Caribbean crown, Barbados is one of the most popular island destinations and with one step on the sands, you’ll understand why. Home to stunning resorts with a whole host of facilities, it’ll be so tempting to stay put but don’t give in. Put on your walking shoes and see what beautiful Barbados beholds.
Feel like a local in Barbados as you head down to Oistin’s Fish Fry for some Friday night fun or explore the natural wonder of Harrison’s Cave. Or, if you just want simple relaxation, lounge on one of the sandy beaches with a tropical cocktail to match the light tropical breeze. This kind of bliss can’t be compared.
St. Lucia
Cameras at the ready! St. Lucia is truly stunning, boasting picturesque views everywhere you turn. But, if beach views and mountaintop vistas aren’t enough for you, take an Instagram snap of Sulphur Springs, the world’s only ‘drive-in’ volcano. Once guests get their share of fiery views, they can enjoy a mud bath at the springs, said to have healing properties so you can turn your very own body into a beautiful natural wonder.
Pigeon Island is one of the most popular island destinations, worth the 90-minute drive from the airport. Panoramic vistas brimming with history can be taken in while exploring the relics and ruins of Fort Rodney before stopping for a bite to eat. On-site restaurants Jambe de Bois and The Captain’s Cellar Bar & Restaurant both offer great island cuisine for a delicious lunch or dinner in the sun.
The Bahamas
Paradise never looked so good. Made up of more than 700 islands and cays, it’s incredibly easy to get lost in The Bahamas. But, find your bearings for a visit to Aquaventure Waterpark. This is a great destination for the whole family with plenty of slides and pools to provide hours of entertainment. Less than an hour from Nassau, the park can be found on Paradise Island where you’ll also find the commanding Atlantis resort.
No trip to The Bahamas is complete without a visit to Pig Beach. Watch the Instagram likes roll in as you take snaps of swimming with these magnificent creatures, totally worth every minute of the three hour boat ride from Grand Exuma.
The gem in the Caribbean crown, Barbados is one of the most popular island destinations and with one step on the sands, you’ll understand why. Home to stunning resorts with a whole host of facilities, it’ll be so tempting to stay put but don’t give in. Put on your walking shoes and see what beautiful Barbados beholds.
Feel like a local in Barbados as you head down to Oistin’s Fish Fry for some Friday night fun or explore the natural wonder of Harrison’s Cave. Or, if you just want simple relaxation, lounge on one of the sandy beaches with a tropical cocktail to match the light tropical breeze. This kind of bliss can’t be compared.
St. Lucia
Cameras at the ready! St. Lucia is truly stunning, boasting picturesque views everywhere you turn. But, if beach views and mountaintop vistas aren’t enough for you, take an Instagram snap of Sulphur Springs, the world’s only ‘drive-in’ volcano. Once guests get their share of fiery views, they can enjoy a mud bath at the springs, said to have healing properties so you can turn your very own body into a beautiful natural wonder.
Pigeon Island is one of the most popular island destinations, worth the 90-minute drive from the airport. Panoramic vistas brimming with history can be taken in while exploring the relics and ruins of Fort Rodney before stopping for a bite to eat. On-site restaurants Jambe de Bois and The Captain’s Cellar Bar & Restaurant both offer great island cuisine for a delicious lunch or dinner in the sun.
The Bahamas
Paradise never looked so good. Made up of more than 700 islands and cays, it’s incredibly easy to get lost in The Bahamas. But, find your bearings for a visit to Aquaventure Waterpark. This is a great destination for the whole family with plenty of slides and pools to provide hours of entertainment. Less than an hour from Nassau, the park can be found on Paradise Island where you’ll also find the commanding Atlantis resort.
No trip to The Bahamas is complete without a visit to Pig Beach. Watch the Instagram likes roll in as you take snaps of swimming with these magnificent creatures, totally worth every minute of the three hour boat ride from Grand Exuma.
frequently asked questions
Does the Caribbean have all-inclusive luxury resorts?
Can I spot whales and dolphins in the Caribbean?
What is the best Caribbean island to visit?
Is it possible to visit more than one Caribbean island in one holiday?
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.