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Luxury Vacations

Not all luxury vacations are created equal. It's a bold statement, but we’d go so far to say that TradeWinds creates dream luxury vacations unlike anything you've ever experienced.

We've handpicked fabulous all-inclusive vacations for you to choose from. Each of these all-inclusive vacations offer something different. From luxury yacht charters sailing stunning waters and unique land-based gastronomic experiences to our exclusive 'Best of Both Worlds' land and sea experiences, we'll help you choose the right luxury vacation.

All you have to do is choose your perfect getaway, leave the office behind and indulge in the ultimate jet-set lifestyle.

Let's get started!

Fall in love with alluring Antigua

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Fall in love with alluring Antigua

Wonderful cruising grounds, steeped in remarkable naval history and home to 365 beaches, Antigua is the perfect destination for a low-key, relaxed vacation.

Relax in the sun and cruise around the island, stopping along the way to enjoy a gentle hike to historic naval Fort Barrington and Fort Berkeley. Recharge your batteries and enjoy secluded anchorages that provide the perfect opportunity to explore Antigua’s stunning deserted white, sandy beaches on foot and by kayak. Picturesque Falmouth Harbour offers a chance to see the world-famous Antigua regatta and mega-yachts of the rich and famous. And get cameras at the ready as Shirley Heights boasts the island’s best views and is the perfect way to watch the sunset. The perfect vacation if you’re looking for a relaxing getaway with plenty of sun, sea and sailing. Famed for its 365 beaches (that’s one for every day of the year), life’s most definitely a beach in Antigua!

Discover paradise in French Polynesia

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Discover paradise in French Polynesia

Remote tropical beaches, shimmering turquoise waters, and in the distance lagoons, atolls and islets - congratulations, you’ve made it to paradise aka French Polynesia!

There are few places like the South Pacific, and those who seek the opportunity to relax and unwind will be rewarded with first-class views, beaches, and sailing. Ease into island life and learn about the production of world-renowned Tahitian vanilla. Set sail for the picturesque lagoons of Bora Bora and Taha’a for amazing diving and indulge in the ultimate sunset cocktail experience. Pamper yourself with an on-board massage and enjoy a visit to the Champon Pearl Farm to try South Pacific pearl harvesting for yourself.

The perfect vacation if you want to chill out, relax and unwind in the ultimate tropical island paradise. Breathtaking beaches, cascading waterfalls and unspoiled natural beauty await you in French Polynesia!

Sublime sailing and diving in St Vincent and the Grenadines

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Sublime sailing and diving in St Vincent and the Grenadines

One of the world’s best-kept secrets, the enchanting islands St Vincent and the Grenadines need to be seen to be believed!

Platinum beaches, inviting azure waters, and of course, the famous Tobago Cays Marine Park give you a taste of 'Old school Caribbean'. Quiet cruising grounds offer a real sanctuary for marine life in Chatham Bay and Mayreau Gardens. Swim with turtles, parrot fish, nurse sharks and eagle rays. Toast a successful dive with delicious coconut cocktails, or uncover your inner pirate on Petit Tabac aka Johnny Depp island!

The perfect vacation if you want to dive straight in and discover an unforgettable Caribbean underwater and 'out of water' experience like no other!

Barefoot fun in the British Virgin Islands

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Barefoot fun in the British Virgin Islands

Breathtakingly beaches, incredible turquoise waters and picture perfect atolls, ideal for sailing, swimming, and snorkeling are just some of the delights that await you in the British Virgin Islands.

With over 60 islands in its archipelago, the British Virgin Islands provide a wealth of fun for those looking for excitement and adventure. As well as being famous for diving and sailing, discover wonderful hidden treasures, such as ‘Bubbly Pool’ – nature’s very own Jacuzzi, the Baths and North Sound, known as a playground for water sports including hobie cats and windsurfing. Visit local hangout Foxy’s and ‘Willy Ts’ floating bar for some well-known Caribbean hospitality. And don’t forget to try the famous Pusser’s rum!

The perfect vacation if you want to experience a week of fun in the Caribbean sun. Make the British Virgin Islands the perfect base for all your sailing adventures!

Give into glorious Guadeloupe

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Give into glorious Guadeloupe

Set sail around the enchanting butterfly-shaped island of Guadeloupe and discover a wonderful mix of French and Caribbean hospitality.

A photographer’s dream, find yourself surrounded by lush mountains offering stunning panoramic views and great hiking opportunities. Wander through colorful villages to truly indulge in island life and visit local distilleries and toast ‘à votre santé’ with new friends. Experience longer cruises and find secluded anchorages, perfect for exploring an exciting underwater marine world or exploring pretty beaches on stand up paddle boards and ocean kayaks. Witness Guadeloupe’s green flash - the breathtaking moment that occurs just after the sun sets over the horizon.

The perfect vacation if you want to discover the wonderful secrets of the ‘Island of Beautiful Waters’ and experience a variety of fun activities in Guadeloupe!

Fun in the sun in St Martin

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Fun in the sun in St Martin

Known as the ‘Crossroads to the Caribbean’, this charming dual island nation is so good, they named it twice!

Boasting a tropical climate, enchanting sandy beaches and exciting dive sites St Martin is definitely the island for activity seekers. Slip on your sneakers and hike up to the mountain top for spectacular views of neighboring St Barths. Or slip into stunning azure waters and snorkel with an array of marine life at the famous Creole Rock or Tintamarres’ Tug. Explore the coastline on a sea kayak and enjoy the sights and sounds of true Caribbean living.

The perfect vacation if you’re looking for fun in the sun, exciting adventures and a true taste of the Caribbean!