Windward Islands

Windward Islands

Windward Islands

Time Zone: GMT-04:00 (Local Time: 02:21)

Historic, unspoiled and enchanting are the elements that make The Windward Islands the diamond of destinations in the Caribbean, and ExecutivEscapes concierges are the Caribbean charter yacht specialists who bring the best of this world to you. Many of the Windward Islands carry a canopy of lush tropical rainforest, while on the shorelines you will discover that secluded and sheltered anchorages, and captivating, palm-fringed beaches, are in abundance. Also, picturesque small villages, where carefree islanders from another culture make you feel most welcome, are scattered across the islands and around the bays. As the name suggests, balmy trade winds blow consistently across this region, so not surprisingly, the majority of charterers choose the experience of being under sail when cruising the Windward Islands.

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The mantle of ‘the Nature isle of the Caribbean’ sits comfortably with Dominica. Its natural attributes are almost beyond compare – verdant and dense rain forests that sprawl across the mountains, volcanic activity, the world’s second-largest hot spring, and matchless plant, animal and birdlife.This is where you can go ashore from your caribbean charter yacht and bask on numerous unspoiled white sandy beaches, claiming them as your very own retreat from the everyday world. When the urge takes you, you can swim in volcanic bubbles while millions of colors dash by, or perhaps in its magnificent steep, narrow stretches of red mud and lush forests on your climb up a mountain volcano. In Dominica, Mother Nature comes to you.


Walk in the footsteps of Christopher Columbus, delight in some of the most magnificent scenic beauty to be found in the Caribbean, and savor the pleasures of French gastronomic flair in its many restaurants and cafes. Known as the Island of Flowers, this French outpost in the Caribbean is a destination full of scenic and culinary surprises. The bustling capital, Fort de France, is particularly French and exciting making it one of the most cosmopolitan islands around. If it is peace, serenity and seclusion you seek, then it is close at hand on the variety of white sand beaches and tropical rain forests. The island’s heavily indented coastline provides the opportunity for many voyages of discovery, to isolated beaches, tranquil palm-fringed bays, and anchorages that are embraced by shorelines untouched by nothing more than Mother Nature herself.


St Lucia sits like another beautiful pearl in the entrancing string of Windward Islands. It is everything you dream on your luxury caribbean charter yacht; a destination teeming with cultural treasures and relics to natural wonders like the colorful and spectacular wildlife to be found in the tropical rain forests, With a lush interior featuring towering mountains, dense rain forest, fertile valleys, and acres of banana plantations, St. Lucia is mostly distinguished by the Pitons—twin peaks that soar high above the ocean floor on the southwest coast. You can top up your tan by lazing on a beautiful beach; dive or snorkel on vibrant coral reefs, or fish for the big ones without failure.


The eight-island archipelago of Iles des Saintes, often referred to as Les Saintes, dots the waters off the southern coast of Guadeloupe. The islands are Terre-de-Haut, Terre-de-Bas, Ilet à Cabrit, Grand Ilet, La Redonde, La Coche, Le Pâté, and Les Augustins. Columbus discovered them on November 4, 1493, and christened them Los Santos (Les Saintes in French) for All Saints' Day. Only Terre-de-Haut and Terre-de-Bas are inhabited, with a combined population of little more than 3,000. Many of the Saintois are fair-haired, blue-eyed descendants of Breton and Norman sailors. Unless they are in the tourism industry, they tend to be taciturn and standoffish. Fishing still is their main source of income, and they take pride in their work. The shores are lined with their boats and filets bleus (blue nets dotted with orange buoys.) The underwater world of Les Saintes is the host for divers who experience the beauty of the multicolored reefs and the captivating underwater grottos. Pigeon Island is the home of the Jacques Cousteau's marine sanctuary, and a must see for the dive enthusiast.


Columbus sighted this 60-square-mile island on November 3, 1493, named it after his flagship, the Maria Galanda, and sailed on. It's dotted with ruined 19th-century sugar mills, and sugar is still its major product. Honey and 59% rum are its other favored harvests. You should make it a point to see one of the distilleries. With its rolling hills of green cane still worked by oxen and men with broad-brim straw hats, it's like traveling back in time to when all of Guadeloupe was still a giant farm. The country folk here are still sweet and shy, and crime is a rarity.You can see swarms of yellow butterflies, and maybe a marriage carriage festooned with flowers, pulled by two white oxen. A daughter of the sea, Marie-Galante has some of the archipelago's most gorgeous, uncrowded beaches. Take time to explore the dramatic coast. You can find soaring cliffs—such as the Gueule Grand Gouffre (Mouth of the Giant Chasm) and Les Galeries (where the sea has sculpted a natural arcade)—and enormous sun-dappled grottos, such as Le Trou à Diable, whose underground river can be explored with a guide. Port Louis, the island's "second city," is the new hip spot, and it's also on the charts for yachts and regattas.


Without question, Barbados is the "most British" island in the Caribbean. Afternoon tea is a ritual, cricket is the national pastime (a passion, most admit), and dressing for dinner is a firmly entrenched tradition. And yet, Barbados is hardly stuffy—this is still the Caribbean, after all. Rather, Barbados is a sophisticated tropical island with a rich history, lodgings to suit every taste and pocketbook, and plenty to pique your interest both day and nights

Sample Itinerary

Please contact one of our agents in order for them to present you with a customized sample itinerary based on your preferences.

Travel Essentials

All Yachts Available in the Windward Islands

184 yachts match your search criteria


60 Prestige

60.00 Ft | Motor Yachts | 2017



27.00 m | Motor Yachts | 2013


Ad Astra

56.00 Ft | Catamarans | 2020



62.00 Ft | Catamarans | 2017



20.00 m | Catamarans | 2021



30.00 m | Sailing Monohulls | 1991


Almyra Ii

49.00 m | Sailing Monohulls | 2000



78.00 m | Motor Yachts | 2011


Amica Mea

152.00 Ft | Motor Yachts | 2004



16.00 m | Catamarans | 2021



50.0 Ft | Sailing Monohulls | 1997



157.00 Ft | Sailing Monohulls | 1983



17.00 m | Catamarans | 2018


Aren’t We Lucky

46.00 Ft | Catamarans | 2019



124.00 Ft | Motor Yachts | 1979



19.00 m | Catamarans | 2012



150.00 Ft | Motor Yachts | 2003



62.00 Ft | Catamarans | 2018


Aspen Alternative

164.0 Ft | Motor Yachts | 2010



49.00 m | Motor Yachts | 1970

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