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The Windward Islands

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Windward Islands Charter

A Windward Islands charter adventure will take you from the southern end of the arc of Caribbean islands, stretching from Martinique to Grenada. A less traveled route than the northern end of the chain, these magical isles offer a mix of longer and shorter passages through dramatic vistas, serene bays and deserted beaches.

Caribbean yachting destination St. Lucia is known around the world for its twin peaks, the Pitons. Martinique offers French culture and cuisine. The 32-island chain of St. Vincent & The Grenadines are a sailor’s playground with just eight islands populated – although when it comes to beautiful Bequia, it seems the celebrities outnumber everyone else.

The Grenadines

Cruising south from St. Vincent, you’ll find the Grenadines lined up like pearls in a necklace, making it easy for a charter itinerary to include them all. On Bequia, you can visit upscale boutiques and restaurants. On the private island of Mustique, you can take a golf-cart tour of the manicured lawns and spectacular homes before heading to the Firefly for a sunset cocktail.

South, between Mustique and the Tobago Cay is a protected park and wildlife sanctuary that stretches for about five miles and includes the isles of Canouan and Mayreau. Here the waters are a deep aquamarine, filled with colorful coral reefs, large sea turtles and tropical fish, and ideal for snorkeling. The anchorages are spectacular, making each meal taken on the flybridge or the aft deck a memorable occasion.

From the Tobago Cays, head south to Union Island, which has a small airport, or continue on to the larger island nation of Grenada. Coming into the St. George’s Harbor, with its tall hillsides studded with homes, you’ll feel like you’re returning to a port in the Western Med.

Each day should start with …

‘What do you want to do today?’

Once you have decided on the destination, there remain endless possibilities

Our charter agents frequently travel to locations far and wide inspecting yachts and visiting crew and are familiar with most favorite destinations. Their expertise is invaluable when it comes to assisting with your plans to maximize your quality time. If you are an active, on-the-go individual or simply prefer to relax with a book, or if you enjoy people watching or crave a trendy night spot, your charter agent can assist. Along with your captain and crew, we are here to ensure you have an exciting, fun-filled holiday.

Request your sample itinerary for The Winward Islands HERE.


Grenada is known as the Isle of Spice and savoring the local cuisine is a must. Try the Spicy Pumpkin Soup and Callaloo Soup. Of course, Breadfruit finds its way into many dishes. Breadfruit is like a starchy melon eaten before it’s fully ripe  The texture and taste are similar to fresh bread. Don’t forget a sweet treat – Enjoying a nutmeg ice cream cone under the shade of a palm tree is perfect for keeping cool in the hot Caribbean sun.