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!

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!

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!

All aboard for Antigua

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All aboard for Antigua

With 365 beaches, 54 miles of stunning coastline and perfect Caribbean cruising grounds for fast, exhilarating sailing, Antigua is definitely the place to be!

Discover Antigua’s fascinating naval history and take a scenic hike to Shirley Heights for the best views of the island. Visit Great Bird Island to see indigenous reptile species such as the Antiguan racer in their natural habitat or relax on one of the many beaches with a book under a palm tree. The warm, azure waters that surround this charming island are delightful for sailing and snorkeling. Explore Sunken Rock and the Pillars of Hercules and snorkel with an array of amazing marine life including Hawksbill turtles and rays.

The perfect vacation if you want to enjoy a range of activities on land and at sea. Come and see why Antigua is everyone’s favorite playground!

Mediterranean magic in Greece

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Mediterranean magic in Greece

Uncover the magic of the Mediterranean and discover the amazing mythology of Greece and the stunning Ionian islands.

Picturesque fishing villages, beautiful natural bays and breathtaking scenery are just some of the wonderful that Greece has to offer. Step back in time and meander through old towns, sample a glass or two of the delicious local Ouzo, or enjoy practising the language with your new local friends! Swim or snorkel in crystal clear waters and feel the warm breeze while you cruise from island to island.

The perfect vacation if you want an active week to truly discover the beauty of Greece, enjoy the amazing Mediterranean culture and cruise around the awe-inspiring Ionian islands!

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!

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!

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