Windward Islands Superyacht Charter

The Windward Islands form the lush southern arc of the Lesser Antilles in the eastern Caribbean, a beautiful chain of dramatic volcanic islands cloaked in rainforest and ringed by golden beaches and clear turquoise water. Wilder and greener than their northern neighbours, they offer some of the most scenic and rewarding cruising in the region.

The chain embraces a wonderful diversity of islands, from the dramatic Pitons of Saint Lucia and the Nature Island of Dominica to the fragrant Spice Island of Grenada and the beautiful Grenadines. Each offers soaring rainforested peaks, colourful culture and stunning natural beauty.

Blessed with steady trade winds and clear waters, the Windwards are a paradise for sailing, offering superb passages between islands, vibrant reefs and countless beautiful anchorages. The clear turquoise seas are ideal for swimming, snorkelling and diving.

Ashore, the islands offer celebrated cuisine, vibrant music, rich Creole culture and warm hospitality, along with dramatic scenery and lush nature. Their beauty and vitality are appealing.

With their rainforested peaks, golden beaches and superb sailing, the Windward Islands are a lush jewel of the Caribbean. Guests can cruise between dramatic volcanic islands, snorkel vibrant reefs and enjoy the culture and natural beauty of this beautiful southern chain.

The Yachts for charter in Windward Islands

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Curated Selection

Tailored for You
A curated selection of Windward Islands charter yachts directly in your inbox.

Discover Windward Islands

Where to Cruise
A Windward Islands yacht charter is shaped by a collection of distinct places, from well-known ports and waterfront towns to quieter anchorages, island escapes and stretches of coastline best approached from the sea. Together, they create a more layered way to charter.

Highlights

Windward Islands Yacht Charter
Windward Islands yacht charters offer the freedom to experience the destination on your own terms. Each itinerary can be shaped around the way you want to travel, with the flexibility to move between time on the water, moments ashore and the simple pleasure of life on board.

Windward Islands Yacht Charter Enquire

Enquire about a Windward Islands yacht charter to receive current yacht availability, seasonal guidance and expert insight into the cruising areas, anchorages and experiences that best fit your preferred style of charter, creating a clearer route to the right itinerary.

Charter Guide

Windward Islands Yacht Charter Itineraries

The Week Unfolds
Across Windward Islands, each itinerary reveals a different rhythm, from lively ports and waterfront towns to secluded anchorages, island escapes and stretches of coastline best discovered from the sea. Together, they create a more layered way to explore, with every route shaped by the places, experiences and moments found along the way.

Windward Islands Must See & Do

The anchorages, experiences and places that define a yacht charter in Windward Islands, and the ones worth building your itinerary around.
Top Anchorages

Tobago Cays, protected marine park with turtles and coral reef
Admiralty Bay, Bequia, the Grenadines’ most sheltered harbour
Marigot Bay, Saint Lucia, a hurricane-hole cove beneath rainforest
Anse des Pitons, Saint Lucia, anchored between the twin peaks
Prickly Bay, Grenada, a well-protected south-coast base

Top Things to Do

Sail between the Grenadines’ cays on steady trade winds
Swim with turtles in the Tobago Cays marine park
Hike to the Pitons or take a rainforest trail on Saint Lucia
Visit a rum distillery or cocoa estate ashore
Explore Grenada’s spice market and nutmeg processing station

Top Places to Visit

The Pitons, Saint Lucia’s twin volcanic peaks
Bequia, a laid-back sailing hub in the Grenadines
Tobago Cays marine park
Saint George’s, Grenada’s harbour capital
Dominica’s rainforest and boiling lake, for the more adventurous

Windward Islands Charter Guide

Everything you need to know before chartering a yacht in Windward Islands, from the best time to visit to where to drop anchor.
When should I charter through the Windward Islands?

The Caribbean dry season, from December to April, brings the steadiest trade winds and least rainfall, and is the most popular window. May and June also sail well, with quieter anchorages and lower rates before the Atlantic hurricane season sets in.

What's the best gateway airport for a Windward Islands charter?

Most charters begin at one of the chain’s international gateways: Saint Lucia (Hewanorra or George F. L. Charles), Grenada (Maurice Bishop International) or Martinique. Each connects to Europe and North America seasonally, with the yacht based nearby at Rodney Bay, Le Marin or Grenada’s south coast.

Which anchorages define a Windward Islands itinerary?

Tobago Cays and Bequia’s Admiralty Bay anchor the Grenadines’ reputation, while Marigot Bay and the Pitons anchorage are Saint Lucia’s signature stops. Grenada’s south coast around Prickly Bay offers well-protected shelter at the chain’s southern end.

How long does it take to cruise the Windward Islands?

A full run from Saint Lucia to Grenada takes ten to fourteen days at an easy pace. A week suits a shorter leg, such as Saint Lucia through the Grenadines to Bequia, or the Grenadines down to Grenada.

Do I need to worry about hurricane season in the Windward Islands?

The Atlantic hurricane season runs roughly June to November, and Grenada in particular sits far enough south to be considered below the main hurricane belt, one reason it is a popular base at that time of year. Most charter itineraries and yacht insurance are still built around the December to June window for a straightforward booking.

More Information

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