Leeward Islands Charter Itinerary

Leeward Islands Itinerary

Leeward Islands Yacht Charter
The Leewards are the northern half of the Lesser Antilles, and they carry the wreckage of three hundred years of European argument ’ forts on every headland, and islands that changed flags so often the cooking never settled.





For a charter this is close to ideal. The trade wind blows steadily from the east, the islands lie roughly north-west to south-east, and no passage takes more than half a day. What changes between them is everything else: language, currency, cuisine and mood.





Every route we shape is a starting point, not a fixed schedule. Stay a second day where the light is right, move with the weather, or follow a captain who knows the cove worth the detour. That freedom is the point of chartering. What follows is one considered way to read the Leeward Islands; the rest we tailor to you.
Day 1

St Martin

One island, two countries, and a border marked by a stone nobody guards. The Dutch side keeps the marinas and the noise, the French side the bakeries and Orient Bay. Watch the aircraft drop over Maho Beach if you must. Then a chef’s dinner on deck, and an early night before the trades.
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Day 2

Anguilla

Anguilla is flat, dry and almost entirely beach. Anchor at Sandy Ground, take the tender to Scilly Cay for grilled lobster and a rum punch of unusual conviction, and spend the afternoon doing very little on sand the texture of flour. The island has never courted anybody, and is all the better.
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Day 3

St. Barths

French, expensive and entirely unapologetic about either. Gustavia holds the boutiques; the hill behind holds Shell Beach. St Jean has the beach clubs, the airstrip and a landing approach that thrills everyone but the pilots. Dinner ashore is as good as anywhere in the Caribbean, and priced accordingly.
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Day 4

St. Barths to Antigua

A proper passage at last ’ eighty miles south-east, close-hauled or on the beam depending on the season, with flying fish going off the bow. Antigua rises green in the afternoon. Anchor in English Harbour, walk up to Fort Berkeley at the entrance, and take a drink on deck as the anchorage fills.
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Day 5

Antigua

Antigua claims three hundred and sixty-five beaches and does not appear to be exaggerating. Half Moon Bay on the Atlantic side is the finest, and usually empty. Nelson’s Dockyard is a working Georgian naval yard, still repairing boats. Shirley Heights on a Sunday evening, for the view and the steel band.
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Day 6

St Kitts & Nevis

Brimstone Hill is a fortress the British spent a century building and the French took in a month. Mount Liamuiga is a volcano with a crater you can climb into. Nevis is quieter still: Nelson married here, Hamilton was born here, and the peak keeps its own permanent cloud. Anchor off Pinney’s Beach.
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Day 7

Return to St Martin

A last reach north with the wind free and the islands falling away astern one at a time. There is time for a final swim, and time ashore for whatever the week left undone. Seven days, four countries, and no passage longer than an afternoon. The Leewards are the easiest sailing in the Caribbean.
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Leeward Islands Yacht Charter Enquire

Enquire about chartering in Leeward Islands to receive current yacht availability, seasonal guidance and expert insight into the cruising areas, anchorages and experiences that best fit your preferred style of charter, creating a clearer route to the right itinerary.