charters · Sag Harbor

SailHamptons

The largest crewed sailing capacity on this page. Luna is a Coast Guard-certified Bermudian schooner the operator describes as having "the largest decks and passenger capacity of any charter sailboat in the Hamptons", carrying 41 guests with three to four crew aboard. Cosmos, a Coast Guard-certified mahogany performance trimaran, is certified for a capacity over 20 and reads as more intimate for smaller groups. A third boat, Starlight — a 57' French sailing yacht designed by Bruce Farr, "the queen of the fleet since 2016" — is not Coast Guard-certified for Hamptons waters and so carries at most six passengers, is booked Monday through Thursday only, and starts at $3,200 for a 3-hour sail with captain and mate. Charters sail from Sag Harbor, Shelter Island and Greenport, from a couple of hours to a full day. Booking is by phone or email only, not an online calendar.

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Cross-reference the full On the Water guide.