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Leeward Islands | Caribbean Yacht Charters

St. Maarten / St. Martin | Anguilla | St. Barths | Antigua | St Kitts and Nevis

Laid out in a gentle arc between Puerto Rico and Dominica, the Leeward Islands present a beguiling range of locations. Each is markedly different, yet their close proximity and generally calm waters make for fantastic cruising grounds.

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Leeward Islands | Caribbean Yacht Charters

Caribbean Yacht Charter Vacations

On one side, each island faces the mighty Atlantic, and on the other, the calm waters of the Caribbean gently caress their shores. The variety and ease means this is a popular area, no doubt helped by the fact that one of the prime Leeward ports of call is the super-stylish island of St. Barths.

This famous isle is a mainstay of so many charter itineraries. Those who want a spot quayside in St. Barths on New Year’s Eve – one of the best places in the world to ring in the New Year – or during the St. Barths Bucket superyacht regatta better make their reservations well in advance.

The Leeward Islands

The Leeward Islands are made up of St. Martin, St. Barths, historic Antigua and lush St. Kitts and Nevis. This seven day itinerary gives you the highlights: one day you will find yourself at the top of Shirley Heights overlooking Nelson’s Dockyard in Antigua, and the next you are navigating the waters surrounding St. Kitts and Nevis.

Chart a Course to Discover the Caribbean and the Leeward Islands

It is the perfect mix of everything and nothing; perfect for those wanting to sample what the Caribbean has to offer, from its flashy to its natural side. You’ll be hard pressed to find a better Caribbean primer if you tried.

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Leeward Islands | Caribbean Yacht Charters

St. Maarten/St. Martin

Divided by Dutch and French settlers, the island of St. Maarten/St. Martin has numerous superyacht marinas and an international airport, making it the logical place to start a charter in the Leeward Islands.

After settling in on board, head over to Orient Bay, one of the best beaches in the Caribbean. After a visit to Sunset Beach Bar, you’ll return to the yacht for dinner.


After a leisurely breakfast, a short hop north means you’ll be in Anguilla in time for lunch. Drop the anchor off Sandy Ground and visit Scilly Cay, a restaurant on a tiny cay in the middle of Island Harbour Bay that specializes in lobster.

Write off the rest of the afternoon as you drink fantastic rum cocktails and eat delicious barbecued lobster on this tiny island with white sandy beaches and palm trees. Can it really get any better than this?

Yacht Charter to the Caribbean - The Leeward Islands

Anguilla to St. Barths

Time for the French chic and exclusivity of St. Barths, where the rich and famous have been vacationing for decades. The main port of Gustavia has excellent high-end shopping, from Cartier to Chanel, lining the quayside where the superyachts moor. Stroll, shop and while the day away sitting in cafés. But don’t forget the island’s natural beauty – take a lap in the tender, stopping at any of the 32 gorgeous beaches that take your fancy. In the evening, book a table at Eden Rock hotel or Bonito, for a very special dinner.

St. Barths to Antigua

From St. Barths, head southeast for Antigua. Arrive in time for lunch and spend the afternoon exploring Nelson’s Dockyard on foot or walk to Fort Berkeley with its fantastic views. In the evening, sit out on deck with a large rum cocktail.

St. Kitts to St. Maarten

If you start the cruise back to St. Maarten early, you could spend a few hours at anchor playing with the water toys, or you could return to your berth and do some serious shopping to cap off your lovely vacation.

Leeward Islands | Caribbean Yacht Charters


Take the tender out to explore Antigua, and the south coast’s beautiful, white-sand beaches in particular. Despite the popularity of luxury yacht charters in Antigua, it is still possible to find secluded anchorages. Back at the marina, grab a taxi and take a trip up to Shirley Heights, where you get spectacular views at sunset.

Antigua to St. Kitts and Nevis

After breakfast, make for the islands of St. Kitts and Nevis. It’s the Caribbean as it used to be – St. Kitts hasn’t changed much in 50 years, the one exception being the now-open Christophe Harbour superyacht marina. There’s plenty to do here on the island though, from epic volcano hikes to scuba diving and zip lining, too. Have a sundowner at SALT Plage bar at Christophe Harbour, and dine on board your yacht.

Westport Yacht Charters

Dimensions, weight, performance and capacities where shown are approximate. Speeds, weight and other performance estimates, if shown or discussed, are estimates only and are not guaranteed. Photos may show optional equipment. Optional equipment may be shown. Specifications and equipment are subject to change without notification. Please consult your Westport sales representative for complete details.

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