Yacht Charter Windward Islands

The Windward Islands are the southern, usually bigger islands of the Lesser Antilles, within the West Indies. As a group they begin from Dominica and reach southward to the North of Trinidad & Tobago.

The trans-Atlantic currents and winds that provided these boats were brought by the fastest route across the ocean to the rough dividing line between the Leeward and Windward islands. Typically, Windward Island charter vacations start from bases on Martinique, St. Lucia, St. Vincent or Grenada.

Those wanting to relax, or fledgling skippers who wish to ease into the Caribbean charter encounter, can stay close to home and seaport -hop along the leeward western coast of any of the bigger islands.

Windward Islands Sailing


Tropical rainforests, barrier reefs, secluded anchorages: In the Windward Islands, you’ll get a taste of all that the Caribbean has to offer, and lots of excellent trade wind sailing to boot. For charter sailors, there are multiple options to begin and end your experiences, and from some of them, you can decide to make your sailing vacation as laid-back or as challenging as you’d like. Along with all those two bookends, the other large islands in the group include St. Lucia and St. Vincent, the capital of St. Vincent and the Grenadines. The Grenadines include bustling Bequia and Union Island, as well as several smaller, more distant islands as well as the otherworldly Tobago Cays.

Windward Islands Boat Charters

The primary high season in the Caribbean is from mid-December to March, when the winter escapees from Europe and North America arrive in their best numbers. The hurricane season is from late July to early October. Although hurricanes are usually uncommon, this really is still the most inexpensive time for chartering in the Caribbean and there are a few really good deals available – however, together with running the risk of thunderstorms, this time of year also has a tendency to be related to lighter (or non existent) winds.


Fill the form and get a quote

Few and simple steps to let us find you the perfect yacht and the route for your yacht charter Windward Islands, with all the extras you wish. Select the type of vessel(s) you are thinking about, the period and the area(s) you would like to discover. Or just tell us the type of holiday that will better accommodate you and your guests. We will find you the boat for your holiday in Windward Islands and the Caribbean Sea. Just one minute of your time to receive from our team your tailor made solution. The most desirable yachts in Sicily are only available on Your Boat Holiday.


Windward Islands Yacht Charter Experts

Our experienced and world travellers, expert Charter Managers visit and sail aboard our selected yachts regularly and are perfectly placed to offer you transparent, tailor and professional advice. Our twenty years of experience in yacht charters, developed in the Caribbean, enabled us to create close, enduring relationships with our clients, investing directly in our yachts and services.


Sailboat, motor yacht or Windward Islands catamaran charter?

Choosing the right yacht for your perfect sailing holiday is not an easy task. If you prefer relaxed, comfortable cruising holidays, a sailing yacht would be the perfect choice for you. A motor yacht, on the other hand, is the best choice for all speed loving people who love the luxury and greater comfort. Find out which boat is best fit for your Windward Islands Yacht Charter.

Join with us your Windward Islands boat charters experience, choosing high quality boats, skippered by professional trainers, to sail in Martinique and Dominica: rent a sail boat, catamaran, motor boat, gulet or charter luxury yacht for Windward Islands sailing.

Windward Islands Boat Charters Top Destinations


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Yacht Charter Itineraries for Sailing Windward Islands

Unlike the rest of the Windwards, Martinique has a distinctive French flair to it. Typical itineraries include a sail north to Martinique or south to the Grenadines; an overnight stop at the iconic rock spires called the Pitons, on the island’s southern tip, is crucial. Charterers beginning from St. Vincent will certainly make a beeline to Bequia’s Admiralty Bay, and from there to the center of the Grenadines.

7 Days Sailing Windward Islands


Day 1st St Vincent
Day 2nd Mustique
Day 3rd Canouan
Day 4th Mayreau
Day 5th Tobago Keys
Day 6th Petit St Vincent
Day 7th Grenada

Sailing Route from St Lucia


Day 1st St Lucia
Day 2nd Pitons
Day 3rd St Vincent
Day 4th Wallilabou Bay
Day 5th Petit Nevis
Day 6th Tobago Cays
Day 7th Salt Whistle Bay, Mayreau