Galeon 510 Sky Deck is a stunning 2019 Galeon 510 Sky Deck Motor Yacht (restored in 2025), available for unforgettable private charters from Sag Harbor.
"Captain Gary and Connie were great. Boat was immaculate and we felt safe and cared for." — Caralyn,
Step aboard The Blue Fin IV, a beautifully restored 1968 Custom Ray Chi Chi 41 Sportfish, expertly refurbished in 2019 and based in scenic Greenport.
"An easy to book experience, we knew exactly what to expect and it was a wonderful way to soend the afternoon." — Bridget,
Experience timeless elegance and adventure aboard Montauk Venture Charters, a beautifully restored 1961 Hatteras Sportfish Motor Yacht, fully refreshed in 2020.
Experience Montauk from the water with a Grady-White 30 and enjoy a private charter designed entirely around your group.
Set sail with VitaminSea Voyages, a premium boating experience departing from the scenic shores of Montauk aboard a 2011 Steiger Craft Miami Cuddy Cabin.
"Bachelor party sunset cruise was excellent! The captain and crew made us feel safe and really took care of us." — Carlos,
Step aboard CrunchTime Sport Fishing, a fully restored 1978 Rose Brothers Custom Charter Headboat, designed for comfort and performance.
Embark on a luxurious and unforgettable journey with One More Drift Charters, operating a beautifully restored 1989 Viking Convertible Sportfish, based in scenic Clinton.
Come Sail with Captain Joy! Looking for an unforgettable experience on the water? Step aboard with Captain Joy — a USCG Master Captain with 40+ years of sailing adventures across the globe.
"Joy was an incredible captain for our fathers day evening sail." — Amy,
FV Kelly Marie Boat Cruises is a classic 2004 Terry Jason Lobster Downeast vessel, beautifully suited for comfortable and intimate private charters departing from Groton, Connecticut.
Discover Sag Harbor boating charters and experience a storied harbor at the heart of the Hamptons. Sheltered waters, classic village views, and easy access to surrounding bays make this destination ideal for every kind of on-the-water adventure, from relaxed cruising to active days exploring.
Launch from Sag Harbor's calm marina basin into the Peconic and Gardiners Bay system, where gentle conditions and broad horizons suit sailing yachts, motorboats, and catamarans alike. Nearby coves and sandbars invite swimming and paddle stops, while longer itineraries can loop around Shelter Island or trace the shoreline toward scenic points and quiet anchorages.
Skippers appreciate clear channels, reliable moorings, and plentiful services that keep turnarounds smooth. Families and groups love sunset cruises along the village waterfront, dolphin and seabird spotting in open reaches, and leisurely picnic runs to tucked-away beaches accessible only by boat.
Anglers find productive grounds seasonally, and day boaters can plan easy hops between waterfront eateries and beach clubs. Photographers will enjoy weathered docks, classic wooden boats, and golden-hour light across the harbor—signature moments that make every outing memorable.
Whether you're booking a captain-led tour or a bareboat rental, Sag Harbor offers flexible routes, protected passages for comfort, and quick access to both lively scenes and serene escapes. It's a refined yet relaxed boating hub where itinerary options are as open as the horizon.
