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The top boating charters in Southold

Southold

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Set sail with North Fork Adventures Charters, a 2001 Parker 2510 Pilothouse offering unforgettable boating experiences from Southold! 

North Fork Adventures Charters

Embark on a luxurious and unforgettable journey with One More Drift Charters, operating a beautifully restored 1989 Viking Convertible Sportfish, based in scenic Clinton. 

One More Drift Charters

Experience timeless elegance and adventure aboard Montauk Venture Charters, a beautifully restored 1961 Hatteras Sportfish Motor Yacht, fully refreshed in 2020. 

Montauk Venture Charters

Step aboard CrunchTime Sport Fishing, a fully restored 1978 Rose Brothers Custom Charter Headboat, designed for comfort and performance. 

Crunch Time Sport Fishing

Discover the perfect getaway on the water aboard Nightjack, a 2002 Levy 32sc Cruiser docked in Stonington. 

Nightjack

Montauk charterboat Cujo is a 1977 Bertram Sportfish Sportfishing (restored in 2025), based out of Montauk. 

Montauk charterboat Cujo

Step aboard Four C's, a well-appointed 2002 Pursuit 3000 Offshore Sportfishing vessel based in Montauk, and get ready for an unforgettable day on the water. 

Four C's

D.C. OUTDOOR ADVENTURES is a 2022 Parker 2820 Pilothouse based out of Mastic. 

D.C. OUTDOOR ADVENTURES

Step aboard Rising Tide, a sleek 2017 Mako 21 LTS Center Console, perfect for an unforgettable day on the water. 

Southold: 9 boats available

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