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,
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,
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,
Embark on a luxurious and unforgettable journey with One More Drift Charters, operating a beautifully restored 1989 Viking Convertible Sportfish, based in scenic Clinton.
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,
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.
Step aboard CrunchTime Sport Fishing, a fully restored 1978 Rose Brothers Custom Charter Headboat, designed for comfort and performance.
Discover Greenport, New York, United States—an inviting North Fork harbor town where calm bays, classic marinas, and scenic shorelines set the stage for unforgettable adventures. Greenport boating charters offer easy access to sheltered waters ideal for leisurely cruising, family-friendly outings, and relaxed days on the water.
Launch from Greenport Harbor and explore the picturesque coves and inlets that fringe the North Fork. Enjoy smooth passages perfect for sightseeing, swimming stops, and sunset cruises, or set a course toward nearby islands and quiet anchorages that make day trips feel like mini getaways.
This destination is known for reliable summer breezes, clear vistas across the Peconic estuary, and a vibrant maritime culture that enhances every itinerary. Whether you're planning a casual sail, a private celebration on the water, or a guided fishing and wildlife-spotting excursion, local captains and rental options make it simple to match the vessel and route to your plans.
Between trips, stroll the waterfront village for fresh seafood, dockside views, and historic charm before returning to your boat for golden-hour cruising. From first-time visitors to seasoned skippers, Greenport boating charters deliver the best of coastal Long Island—easygoing conditions, memorable horizons, and a flexible home base for exploring at your own pace.
