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The top boating charters in Southold

Southold

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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

Set sail with VitaminSea Voyages, a premium boating experience departing from the scenic shores of Montauk aboard a 2011 Steiger Craft Miami Cuddy Cabin. 

VitaminSea Voyages

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 The Blue Fin IV, a beautifully restored 1968 Custom Ray Chi Chi 41 Sportfish, expertly refurbished in 2019 and based in scenic Greenport. 

Blue Fin IV Lighthouse Cruises and Eco Tours

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

Nightjack

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

Crunch Time Sport Fishing

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

Rising Tide

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 Steal Your Fish Charters, LLC, a sleek and powerful 2015 Boston Whaler Outrage Center Console based out of New London. 

Southold: 15 boats available

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Southold: 15 boats available