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!

Awesome aquatic adventures in Antigua

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Awesome aquatic adventures in Antigua

It’s no secret that the Caribbean is known to have some of the best dive sites in the world, and Antigua is no exception.

Get ready to experience an aquatic adventure like no other. Dive into crystal clear waters and open your eyes to incredible marine habitat, home to endangered Hawksbill turtles, fish of every size and species, including moray eels, burrfish, and rays, to name a few! With a maximum depth of 120ft Sunken Rock is known as one of the best dive sites in the Caribbean. Antigua offers an abundance of exciting wrecks and colorful reefs and provides an ideal playground for those who want to explore what this charming island has to offer beneath the surface.

The perfect vacation to dive in and discover some of the finest reefs and wrecks in the Caribbean. Amazing marine life, coral reefs, and canyons are waiting to be explored in Antigua’s mesmerizing underwater playground!

Dive in and experience the underwater wonders of Guadeloupe

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Dive in and experience the underwater wonders of Guadeloupe

The Caribbean is known to have some of the finest diving sites in the world, and it’s no secret that Guadeloupe offers a wonderful underwater world that’s waiting to be discovered.

Home to the famous Cousteau Marine Reserve, protected bays provide keen divers of all abilities the chance to experience a perfect diving and snorkeling paradise. Snorkel around volcanos and reefs teeming with fish, discover la Baleine – a protruding reef in the shape of a whale and listen out for whale song – a moment that you’ll never forget. With so many diving highlights, including some ‘secret sites’ not on the itinerary, you’ll find it hard to choose a favorite!

The perfect vacation if you want to experience and explore the world-class diving sites that surrounds the beautiful Caribbean island paradise of Guadeloupe!

Fall in love with alluring Antigua

Go Relax

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!

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!

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!

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!