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!

All aboard for Antigua

Go Active

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!

Bask in the beautiful British Virgin Islands

Go Diving

Bask in the beautiful British Virgin Islands

The definition of perfection and an ideal tropical paradise escape, the British Virgin Islands is one of the Caribbean’s most celebrated cruising destinations.

Breathtakingly beautiful beaches make way for incredible turquoise waters. Dive straight in and explore the historic RMS Rhone or snorkel in the famous Caves amongst colourful corals and schools of fish. Discover the Baths and experience the BVIs secret collection of unique boulders and rock formations - most definitely one for the bucket list!

The perfect vacation if you’re a diving devotee who wants to explore some of the finest reefs, waters and wrecks in the Caribbean!

Fun in the sun in St Martin

Go Fun

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!

Sublime sailing and diving in St Vincent and the Grenadines

Go Diving

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!

Dive in and experience the underwater wonders of Guadeloupe

Go Diving

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!

Awesome aquatic adventures in Antigua

Go Diving

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!