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The top boating charters in Southold

Southold

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

Montauk charterboat Cujo

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

Nightjack

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

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

Crunch Time Sport Fishing

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

D.C. OUTDOOR ADVENTURES

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

North Fork Adventures Charters

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

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 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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