Windward Islands Yacht Charter

Luxury Yacht Charter Guide to the Windward Islands

Part of the Lesser Antilles Caribbean chain, the Windward Islands is one of the most enchanting yachting destinations in the Caribbean.

Calm Caribbean waters, palm-lined sandy beaches, aquamarine sea, and richly tropical volcanic islands create a truly spectacular backdrop for a luxury charter yacht vacation.

Out-of-this-world scuba diving and snorkeling among beautiful corals and tropical fish, secluded beaches, and lush rainforest interiors make the Windward Islands a destination of a yacht charterer's dreams.

Distinct Caribbean culture, delicious cuisine, and plenty of history and heritage gems add to the flavor and spice of the islands. In contrast, the French influence, boutique hotels, and exclusive resorts provide a touch of luxury and sophistication.

Yachts in the the Windward Islands

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st. lucia botanical gardens, diamond waterfall, caribbean
Stairway Pathway on the island of Dominica on Boiling Lake HikeStairway Pathway Dominica
The ancient town hall of Fort-de-France and Aime Cesaire theater. Fort de France is the capital of Martinique island, Lesser Antilles

Reasons To Charter A Yacht In The Windward Islands

Combining dramatic Atlantic Ocean scenery with the iconic tropical paradise of the Caribbean Sea, the Windward Islands stand out as a unique sailing destination.

From Dominica's white sand beaches framed by swaying palms where the Pirates of the Caribbean movies were filmed to Barbados' roaring social life and Grenada's colorful carnivals and music scene, the Windward Islands promise a cornucopia of unforgettable experiences for adventure seekers and luxury-loving bon vivants alike.

Here are some of our favorite reasons to go on a Windward Islands charter yacht vacation:

A Wealth Of Islands

The Windward Islands is one of those rare yacht charter destinations that have an array of islands offering an evolving palate.

The Grenadines boast sandy cays and colorful parrots of paradise, while Dominica is famous for bubbling hot springs and wild trails.

From luxury hideaways on Petit St Vincent to spice tasting on Grenada, the Windward Islands builds a world of vivacious color and texture to enjoy.

Far From Cliché

All the islands in the Caribbean boast those iconic serene lagoons, white sandy beaches, and traditional rum shacks, but some of the Windward Islands stand out with their unique landscapes and places that remained largely unspoiled for centuries.

Dominica offers a completely new and wild side of the Caribbean with its sulfur pools, milky white waters, and dark jungle with twisted vines, while Indian Rivers make for a refreshing feel for those who are used to the usual hues of the Caribbean.

St Lucia's twin pitons standing sentinel over the sea appear like they've been dropped here straight out of the Avatar movie, and the stunning natural beauty of Grenada's rugged mountains and rainforests rival the Amazon.

A Hiking Haven

Visiting St Lucia’s Pitons or the Morne Trois Pitons National Park, hikers will be in their element as soon as they step ashore on the Windward Isles.

Whether you enjoy strenuous hikes up the side of craggy volcanoes or gentle strolls through rainbow-feathered feathered rainforests, you can walk for days around the Windward Islands and never grow tired of her natural beauty.

The Caribbean Spirit

The spirit of the Windward region is all about color, spice, and fabulous festivity. These islands are best known for their calypso street parties, intricate carnival costumes, and charismatic locals.

Rum-tasting tours, dining on fresh lobster swimming in coconut and spice, and the energetic live music scene of Mustique are all on the menu in the Windward Islands, along with intriguing local history, heritage, and pirate legends.

Martinique and wind
Caribbean Martinique beach coconut
exotic beach at St. Lucia, between the two Pitons, St. Lucia, Caribbean

Windward Islands Yacht Charter Destinations

While the Lesser Antilles is a popular yacht charter destination, choosing which Windward Islands to visit can be a tricky task.

Each is unique in its own way: from the lively beats of reggae and soca on Union Island to the French chic of Martinique and from the spice plantations of Grenada to Dominica's unbridled wilderness, every island is intriguing in its own right.

Here are the most popular yacht charter vacation spots in the Windward Island group:


The famous birthplace of Rihanna and rum, Barbados is sometimes classed as part of the Leeward Islands, although its close proximity to Saint Lucia and the Grenadines put it in the Windward group.

A flat tropical Caribbean island with gentle slopes and hills, Barbados is teeming with sugarcane fields, tropical fruit orchards, and fields of vibrant flowers. Barbados has a network of subterranean caverns, some of which are accessible to visitors, and large, gradually sloping beaches perfect for swimming and sunbathing.

Known for excellent surf and snorkeling spots, powdery pink sand, and picturesque anchorages, Barbados is the most easterly island in the region favored by guests of luxury yachts.

In addition to its natural beauty, Barbados is a center for yacht races boasting a lively bar scene, fine dining experiences, and five-star resorts.


One of the traditional spice islands of the West Indies, Grenada combines the best of two worlds. On the one hand, the island has excellent marinas offering all the modern amenities and high-quality services for luxury yachts; on the other hand, Grenada is known for its colorful Caribbean way of life, energetic calypso beats, and carnival traditions.

Inland, Grenada boasts rugged mountain terrain and lush rainforest delightfully spotted with tumbling waterfalls. Its traditional spice plantations still produce nutmeg, cinnamon, and cocoa, while its waters hide an active submarine volcano.

Grenada is known for its beautiful cruising grounds, the bustling waterfront of its capital St George's, and the intriguing Underwater Sculpture Park, worthy of a visit.

The Caribbean hosts some of the world's most intriguing yachting competitions, and boating enthusiasts will appreciate Grenada's renowned sailing events like the Grenada Sailing Week.

Saint Vincent and the Grenadines

Saint Vincent and the Grenadines is an island country consisting of 32 islands. The Grenadines island chain is best known for its serene beauty, secluded beaches, and sheltered anchorages.

Saint Vincent and the Grenadines offer spectacular diving and snorkeling opportunities thanks to its vibrant coral reefs, underwater caves, and marine life teeming with sea turtles and tropical fish. Although most famous for their perfect white beaches, the volcanic island of St Vincent and Union Island stand out with their black sands contrasting against the turquoise blue waters.

For those seeking luxury experiences in the Grenadine islands, the privately owned Young Island offers fine dining experiences; Petit St Vincent boasts a luxury resort, while the quaint narrow streets of Kingstown are lined with glitzy boutiques.

Saint Lucia

St Lucia is guaranteed to take your breath away with the rising splendor of her velvet green pitons - cone-shaped mountains overlooking the sea. The double peaks that punctuate the baby blue sky around the picture-perfect island invite active charter guests out for a morning hike.

No St Lucia yacht charter trip would be complete without exploring the excellent snorkeling and diving spots around the island, where colorful marine life and corals make up a wonderful underwater world.

For those who are feeling a little more dreamy than active, there is still plenty to do on the perfumed shores of St Lucia. Head into Soufriere to explore lost plantations, hit Rodney Bay for a spot of shopping and long lingering lunches, and take a drive around the smoldering volcano.


Beneath the shadow of Mount Pelee, Martinique is a fascinating place that has long lived under the repeated threat of volcanic energy. For nature lovers, the island's black volcanic sand beaches, mangrove forests, and fairytale waterfalls will provide the perfect backdrop for adventure.

For those seeking elegance and luxury, the island has plenty to offer. A French overseas territory, Martinique delivers a touch of modern luxuries and comforts. It's bustling capital and urban sprawl provide shopping, fine dining, and bar-hopping opportunities, and the island's upscale resorts and boutique hotels boast French charm and sophistication.

Martinique's exceptional culinary scene is a must for foodies: here, French cuisine is infused with a Caribbean influence.


A volcanic island featuring mist-cloaked mountains, mysterious boiling lakes, frothy champagne reefs, and daring adventures, Dominica is often dubbed the "Nature Island of the Caribbean" due to its impressive volcanic features and geothermal activity.

Numerous volcanic peaks may be found on the island; one of them, Morne Trois Pitons, is a World Heritage Site. Boiling Lake is the world's second-largest hot spring.

For those seeking a peaceful and secluded Caribbean destination, Dominica may be the perfect choice. It's less developed in terms of tourism compared to other destinations, offering more secluded anchorages and a sense of tranquility. Here, charter yacht guests have the opportunity to indulge in privacy and serenity amidst the stunning natural beauty of the island.

Dominica's friendly locals, vibrant music, cuisine, and traditions offer a glimpse into a laidback Caribbean way of life.

Alternative Windward Islands Destinations

While the Windward Archipelago is a popular yacht charter destination, the entire Caribbean is a stunning region to explore.

Below, we share some of our favorite Caribbean locations to add to your itinerary:

Leeward Islands

Situated between the Greater Antilles and the arch of the Windward Islands, the Leeward Islands are world-famous for their idyllic Caribbean scenery, excellent diving and snorkeling sites, and sailing events.

In addition to paradise islands and aquamarine waters, the Leeward Islands are favored by celebrities and the rich and famous. Luxury resorts and high-end shopping, dining, and boutique hotels abound in St Martin and St Barts, while Antigua and Barbuda is known as the sailing capital of the Caribbean.

When it comes to the Caribbean islands combining both luxury, culture, and nature, the US and British Virgin Islands have few rivals. Finally, Anguilla is a sunbathing heaven on earth, boasting no less than 33 white sandy beaches.

Trinidad and Tobago

A twin-island nation just off the coast of Venezuela, Trinidad and Tobago is famous for its Carnival and colorful costumes, steelpan music, and calypso competitions.

Protected anchorages and sheltered bays make Trinidad and Tobago an easily accessible destination, and its picturesque coastline of rainforest-covered cliffs, jagged rocks, and unspoiled beaches provide beautiful cruising grounds.

When To Charter A Yacht In The Windward Islands

The Caribbean's primary high season is from November through until July, when the wonder of the Windward Islands remains open and at her best for off-the-beaten-track exploration.

Similar in tone and temperature to the Leeward Islands, you will find balmy blues and bleached whites create a warm and welcoming environment. The waters around the Windward archipelago are also celebrated as boasting beautiful temperatures.

August through to October is the hurricane season in the Caribbean, and it's best to avoid those months due to stormy and rainy weather.

The Cost of a Windward Islands Yacht Charter

The cost of a Windward Islands yacht charter depends on the type and size of the boat.

On average, a yacht hire will cost somewhere between $20,000 to $50,000 per week, although large and luxurious crewed yachts may cost $1,00,000 per week and upward.

Some superyacht charters can command a price of $200,000 - $1,000,000.

The Difference Between Sailing vs Motor Yacht Charters

Most yacht charters in the Windward Islands are either sailing or motor yachts, with catamarans being extremely popular because of their capacity to access shallow waters.

Sailing yachts are preferred by those seeking an authentic sailing experience. There's something to be said about the romance of harnessing the wind, and sailing yachts are extremely popular in the Caribbean.

Motor yachts are engine-powered boats offering comfort, speed, and luxury. Most luxury charter yacht options are motor boats favored for their spacious decks and cabins, onboard amenities, and other features.

Catamaran Charters

Catamarans are two-hull boats offering plenty of space and stability. Catamarans can be wind or engine-powered, and their smooth movement is appreciated in the tranquil sea of the Caribbean.

Crewed Yacht Charters

Unlike bareboat charters, crewed yachts are the best option for luxury Caribbean vacations. An experienced skipper and a professional crew take care of every single detail - provisions, navigation, itinerary, meals, and more - during the voyage providing guests with a level of comfort and convenience a bareboat charter can never match.

Choosing Luxury Yachts with the Right Features

When looking for charter yachts, it's important to evaluate the amenities and services offered on board.

Large swimming decks and jacuzzis may be prioritized for a romantic sailing vacation.

Water toys are vital for active trips, while onboard entertainment and gourmet meals may be significant for people seeking luxury.

Here are some of the most common characteristics of charter yachts for the ideal Caribbean sailing vacation:

  1. Swimming Deck

If you're looking to experience the ultimate in comfort, convenience, and easy access to the aquamarine waters of the Caribbean, choosing a yacht with a large swimming deck and spacious cabins is key.

For the utmost comfort during the voyage, motor yachts featuring large and low decks perfect for swimming and spacious, well-equipped cabins are the best option.

  1. Water Toys

Enhance your sailing experience with a variety of water toys, including kayaks, paddleboards, jet skis, e-foils, and more.

Choosing a yacht with a selection of water toys will enable you to stay active and make the most of your time on the water.

  1. Gym and SPA Rooms

Swimming, snorkeling, and diving options abound in the Windward Islands while aboard a charter yacht.

An onboard gym and spa room, on the other hand, may enhance the experience of visitors who wish to stay healthy and enjoy wellness treatments while onboard.

  1. Movie Theater

An onboard movie theater is a great way to enjoy some private time while sipping on a cocktail and watching your favorite film.

After all, enjoying a re-run of the Pirates of the Caribbean while sailing the islands where the movies were actually filmed is an adventure in itself.

Book A Windward Islands Yacht Charter Today

The Windward Islands region is a beautiful part of the world, and the best way to see it is on a boat charter. The greatest way to take in the Windward Islands' turquoise waters, palm-lined sandy beaches, spice islands, and distinctive culture is from the comfort of a yacht.

Those visiting the Windward Islands may take in the islands' stunning scenery and enjoy the thrill of unrestricted sailing in the lap of luxury by chartering a yacht.

Start planning a once-in-a-lifetime trip to the Caribbean today by looking into yacht charters.

Windward Islands Yacht Charter FAQs

Why are they called Windward Islands?

The Windward Islands are named so because of their geographical location with prevailing Northeastern trade winds.

The Windward and Leeward Islands are two island groupings in the Lesser Antilles that are called from their physical location in respect to the prevailing winds.

Leeward Islands include Anguilla, Antigua and Barbuda, the British Virgin Islands, Guadeloupe, Montserrat, St Barts, and Saint Kitts and Nevis.

A Windward Islands yacht charter cost varies depending on the boat's size and type: a price range of $15,000 - $50,000 per week is expected, although a luxury yacht charter can cost $100,000 and upward, reaching eight figures.