Marigot Bay, Saint Martin
Great Bay, Sint Maarten
Basseterre Bay, Saint Kitts
Charlestown Roads, Nevis
Fort Bay, Saba
Watch jets skim the sand at Maho Beach, Sint Maarten
Hike Nevis Peak through its rainforest trail
Tour Brimstone Hill Fortress, Saint Kitts
Dive the walls of Saba’s National Marine Park
Explore Fort Louis above Marigot, Saint Martin
Orient Bay, Saint Martin
Philipsburg, Sint Maarten
Basseterre, Saint Kitts
Charlestown, Nevis
The Bottom, Saba
The prime charter season runs from December through April, when the trade winds are steady at twelve to eighteen knots and rainfall is lowest. Many yachts also sail the shoulder months of November and May, before the Atlantic hurricane season peaks from August through October. Water temperatures stay warm year-round, so the main factor in choosing a date is wind reliability and storm risk rather than comfort in the water.
Most charters begin from one of two regional hubs: V.C. Bird International Airport (ANU) on Antigua or Princess Juliana International Airport (SXM) on Sint Maarten, both served by direct flights from the United States and Europe. From either, guests transfer by short inter-island flight or by the yacht itself, since the two hubs sit roughly one hundred nautical miles apart at opposite ends of the chain.
With nine or so islands in the chain, most itineraries link two or three rather than attempting all of them. English and Falmouth Harbours on Antigua, Road Bay on Anguilla and Gustavia on Saint Barthélemy are the classic stops, each combining good holding with lively shoreside dining. Further south, Basseterre on Saint Kitts and Charlestown on Nevis add a quieter, more historic call between the busier hubs.
A week aboard is enough to combine two neighbouring islands at a relaxed pace, for example Antigua and Barbuda or Saint Martin and Anguilla. Ten days to two weeks allows a longer chain, taking in Saint Kitts, Nevis and Saba as well, with time ashore for the fortresses, hikes and dive sites that make each island distinct rather than just another beach stop.
Yes, and it’s worth building time into the schedule for it. Unlike single-nation cruising grounds, the Leewards cross British, French, Dutch and independent territory within a short sail: Anguilla and Montserrat are British, Antigua and Barbuda and Saint Kitts and Nevis are independent, and Saint Martin’s two halves alone answer to Paris and The Hague. Each border change means a fresh clearance, typically handled by the crew while guests relax aboard.
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