Private sailing charters · Mamaroneck, NY
Sail aboard Winsome
A 1966 Mercer 44 yawl, skippered by a USCG-licensed captain. Day sails, overnights and longer cruises for small private groups.
Hull nine of fourteen, and the third Mercer 44 to come out of Cape Cod Shipbuilding.
Charters
Choose your time on the water
Day Sail
Leave the dock at 10:00 and have Long Island Sound to yourselves: time to sail, anchor somewhere quiet for lunch, and ease home on the afternoon breeze, back in Mamaroneck around 4:30.
Overnight
Sleep aboard at anchor and wake on the water. Dinner in the cockpit, a slow morning, and an easy sail back the next day.
Multi-day Cruise
Several days between harbors, with passage planning and the watch schedule handled by the captain. Itineraries are built around your group.
Chef-prepared dining
Winsome’s owner is a private chef and restaurateur with more than 20 years of experience. Chef-prepared dining is available on any charter, planned around your group’s tastes and dietary needs.
The boat
A Bill Tripp design, and the largest fiberglass yacht of her day
Winsome is a Mercer 44, drawn in 1959 by William H. Tripp Jr., the designer behind the Bermuda 40 and the ocean racer Ondine. Tripp designed her to race offshore under the Cruising Club of America rule, and he was an early believer in fiberglass at a time when most yachts her size were still built of wood.
The first six Mercer 44s were built by Mercer Reinforced Plastics in Trenton, New Jersey. Cape Cod Shipbuilding in Wareham, Massachusetts, took over the molds in 1965 and launched Winsome the following year as a yawl, with a second, smaller mast aft. At the time, she was the largest fiberglass yacht in production.
Long overhangs give her reserve buoyancy and a soft ride in a chop, and owners of the class report better than eight knots on a reach. Her keel-centerboard hull draws just over four feet with the board raised, so she can reach shallow anchorages that deeper boats cannot.
Steady under sail
A heavy, long-keeled boat with an easy motion, comfortable for first-timers and experienced sailors alike.
Room to spread out
One open room below, with space for a group to sit, cook and settle in out of the sun.
Properly looked after
Equipped for offshore sailing, with a life raft, distress beacons and AIS aboard. Every charter begins with a safety briefing.
The captain
A licensed captain on every charter
Every Winsome charter is skippered by a U.S. Coast Guard–licensed captain. You can take the helm, trim a sail or simply sit back; the captain handles the boat, the route and the weather.
How it works
From enquiry to cast off
Enquire
Tell us your dates, group size and the kind of trip you have in mind.
Plan
The captain confirms availability, suggests a route for the weather, and sends what to bring.
Sail
Meet at [DOCK / MARINA], hear the safety briefing, and cast off.
Enquire
Check availability
Send a few details and the captain will reply with availability and a quote. Prefer to write directly? [EMAIL ADDRESS] · [PHONE]