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Leeward Islands Charters

Encompassing several different nationalities, the Leeward Islands span some 120 miles from Anguilla to Dominica. They offer a diverse geography ranging from lush rainforests to coral islands to volcanic craters, along with a wide array of cultures and cuisine, perfect for your charter experience.

Dutch Sint Maarten is the winter home to many of the world’s largest megayachts, moored in Simpson Bay. Leaving there, it’s a short run to the French side of this dual-nation island, spelled “St. Martin.” Each side offers very different dining and shopping experiences, while both sides have a variety of snorkeling, swimming, and scuba diving sites for your Caribbean yacht charter.

A short cruise from St. Martin sits the low coral island of Anguilla.  The  island provides an escape from the hustle and bustle of St. Martin and the glitz and glam of St. Barths.  Anguilla is covered in splendidly soft, dazzling white sand beaches and provides an escape to pure relaxation.  For the “tee” lovers in your group, the CuisinArt Resort offers an 18-hole Greg Norman signature designed champion course.

Exclusive St. Barths

Any Leeward Islands charter itinerary must include St. Barths. This exclusive French isle with its picturesque port of Gustavia – lined with designer boutiques and upscale eateries – is a must for yachtsmen and celebrities who appreciate its sophisticated combination of beautiful beaches and chic nightspots.

Moving on to Antigua, you will find another fleet of superyachts nestled in English Harbour. This former British Royal Navy port is rich in history at every turn, but don’t forget to spend an afternoon beachcombing on neighboring Barbuda.

If you have the time, it is worth adding a few more nautical miles to your itinerary to see St. Kitts and Nevis. These sister isles offer the kind of lush tropical setting usually seen in the South Pacific. At the center of St. Kitts is Mount Liamuiga, a dormant volcano covered by dense tropical forest.

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 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 Leeward Islands HERE.


In September 2011, the cuisinart Golf Resort and Spa on the Caribbean island of Anguilla acquired the island’s first and only golf course. The $50 million Greg Norman-designed champions’ course is sure to impress the golfing guest on your charter yacht. For those not keen on hitting the links, the resort’s Venus Spa is sure to relax and pamper.