Week Charter · Leeward Islands
Leeward Islands Week
Seven nights, four or five islands, and the most varied charter route in the Caribbean — link our two home ports, Antigua and St. Martin, taking in Barbuda, Anguilla, and St. Barts along the way.
Private proposals within 48 hours
From
$11,750seven nights
Departure
Antigua · St. Martin · Leeward Islands
Aboard
Cap II · Flying Wing
Our signature week — and the route that links our two home ports. Seven nights starting in one home port (most often Antigua) and finishing in the other (St. Martin) — or run the same week in reverse. North through Barbuda, day-sails to Anguilla and St. Barts, and the southern passage back. Four or five islands depending on weather and pace, all reachable within day-sail distances of each other, and each genuinely different from the next.
The route is shaped by the trades. We typically leave Antigua on a beam reach to Barbuda, lay over for a night at Low Bay, then run north to St. Martin (an overnight or long-day passage). From Marigot or Simpson Bay — our northern home port — the week loops east to Anguilla's Sandy Ground and the offshore cays, then south to Gustavia and Colombier on St. Barts, and finishes either back in St. Martin or with a southern return to Antigua. Both directions work; the wind and your start city decide.
Charter rates start at $11,750 all-inclusive aboard Flying Wing for parties of up to eight. Cap II is available for the week from $32,500 for parties of up to ten. Both rates include the yacht, crew, fuel, mooring, marina fees, and full provisioning of fresh food and drinks. Restaurant nights ashore — Veya, Bagatelle, Grand Case — are arranged on request.
Highlights of this charter
Four to five distinct islands
Barbuda for the empty pink sand, St. Martin for the markets and food, Anguilla for the cays, St. Barts for Gustavia. The variety is the point.
Real sailing
Daily passages between 25 and 80 nautical miles — guests get a real week at sea, not just an extended swim stop. The boat is moving most days.
The best provisioning in the Caribbean
Marigot Tuesday and Saturday markets; Saint Barth's harbour stores; the chandleries of Simpson Bay. The chef restocks once mid-week.
Customs handled
Three or four customs clearances over the week — the captain handles them all. Guests need only a passport.
Sailing this route with RexSailing
Captains who know the route
Our crews have run this loop weekly for years — they know the customs offices, the restaurant calendars, the right bay for each weather window.
Truly private
Your party, your boat, your week. No shared groups, no fixed itinerary — every day is shaped on the morning of, around weather and what the guests want.
All-inclusive
The yacht, the crew, the food, the wine, the marina fees, the customs. Restaurant bills ashore are billed at end-of-charter cost.
Pair this charter with
St. Martin Week Charter
The same northern islands without the long Antigua passages — based out of Marigot for the week.
Explore →
Antigua & Barbuda Week
A quieter, shorter alternative — two islands, less moving around.
Explore →
Antigua Yacht Charter
All charter options from our Antigua home port.
Explore →
Before you enquire
How many islands do we actually visit?
Standard is four — Antigua, Barbuda, St. Martin, and St. Barts. Adding Anguilla makes five. The route is shaped around weather and what the guests want; if a particular island matters to you, tell us early.
Where do we join?
Either home port. Most guests start in Antigua and finish in St. Martin (or vice-versa) — both are direct flights from US/EU hubs and the route works equally well in either direction. One-way charters carry no delivery fee on this route since the boat is moving between its own bases. Private transfer to the marina is arranged on arrival at whichever port you start.
Is the week tiring?
Daily passages are usually 25-50 nm — comfortable beam reaches in the trades. The 80 nm Antigua-St. Martin leg is the longest single passage, often run as an overnight to maximize time on the islands.
Are all the customs clearances really handled?
Yes. We clear in and out of every island as required — Antigua and Barbuda is one country, St. Martin two (clearing the French and Dutch sides separately), Anguilla, St. Barts. The captain pre-files where possible.
The Leeward Islands week is the trip we tell guests about when they ask which charter to do. Tell us your dates and party size; we will hold the boat while we shape the rest.
Find the Right Yacht for Your Charter
Tell us your dates, group size, and preferred experience - we will match you with the ideal yacht.
Private proposals within 48 hours · Enquiries handled discreetly
RexSailing · Antigua · St. Martin