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The top boating charters in Southold

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Sea Lover &ndash; 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. Designed for both relaxation and adventure, this sleek yacht accommodates up to 10 g

Sea Lover – Galeon 510 Sky Deck

Beaver Dam Boat Basin is a 2003 Searay 24 Bay boat (restored in 2023), based out of Blue Point. It can take up to four guests. The boat is powered by one 300 HP gasoline inboard Merc engine, offering a maximum cruising speed of 25 knots. The captain, Kenn

Beaver Dam Boat Basin

Step aboard the legendary CUJO, a beautifully restored 1977 Bertram Sportfish Sportfishing yacht, now better than ever after a full 2025 refit. Departing from iconic Montauk, this classic vessel combines vintage charm with modern comfort, perfect for an u

Montauk Charterboat CUJO

Embark on a luxurious and unforgettable journey with One More Drift Charters, operating a beautifully restored 1989 Viking Convertible Sportfish, based in scenic Clinton. With space for up to six guests, this classic vessel combines vintage charm with mod

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. Perfect for up to six guests, this classic sportfishing vessel combines vintage charm with modern functio

Blue Fin IV Lighthouse Cruises and Eco Tours

Step aboard CrunchTime Sport Fishing, a fully restored 1978 Rose Brothers Custom Charter Headboat, designed for comfort and performance. Based in Montauk, this spacious vessel accommodates up to 27 guests, making it perfect for group excursions, corporate

Crunch Time Sport Fishing

Discover the perfect getaway on the water aboard Nightjack, a 2002 Levy 32sc Cruiser docked in Branford. This beautiful vessel offers ample space for up to six guests, making it an ideal choice for a day out with friends or family. Powered by a 330 HP Cum

Nightjack

D.C. OUTDOOR ADVENTURES is a 2022 Parker 2820 Pilothouse based out of Mastic. It can take up to six guests. The boat is powered by two 300 HP gasoline outboard Yamaha engines, offering a maximum cruising speed of 60 knots. The vessel comes equipped with a

D.C. OUTDOOR ADVENTURES

Come Sail with Captain Joy! Looking for an unforgettable experience on the water? Step aboard with Captain Joy &mdash; a USCG Master Captain with 40+ years of sailing adventures across the globe. Now docked in Westbrook, CT, she&rsquo;s ready to share the

Joyride Charters

Step aboard Steal Your Fish Charters, LLC, a sleek and powerful 2015 Boston Whaler Outrage Center Console based out of New London. Perfect for intimate outings, this premium vessel comfortably accommodates up to four guests and is powered by twin 300 HP M

Southold: 15 boats available

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Southold: 15 boats available