Southold Boat Tours
The best out of 14 boat tours in Southold - enter dates to check availability
North Fork Adventures Charters
5+ external reviews
Southold
Set sail with North Fork Adventures Charters, a 2001 Parker 2510 Pilothouse offering unforgettable boating experiences from Southold! With room for up to six guests, this sturdy and well-equipped vessel is powered by twin 150 HP Yamaha outboard engines, c
Blue Fin IV Lighthouse Cruises and Eco Tours
4.9
/5
(12 external reviews)
Greenport (9 min drive from Southold)
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.
5+ external reviews
Westbrook (3 hr 14 min drive from Southold)
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.
5.0
/5
(182 external reviews)
Clinton (3 hr 6 min drive from Southold)
Embark on a luxurious and unforgettable journey with One More Drift Charters, operating a beautifully restored 1989 Viking Convertible Sportfish, based in scenic Clinton.
Sea Lover – Galeon 510 Sky Deck
Sag Harbor (1 hr 16 min drive from Southold)
Sea Lover – 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.
4.3
/5
(1 review)
Montauk (1 hr 34 min drive from Southold)
Step aboard CrunchTime Sport Fishing, a fully restored 1978 Rose Brothers Custom Charter Headboat, designed for comfort and performance.
5.0
/5
(33 external reviews)
Montauk (1 hr 54 min drive from Southold)
Set sail with VitaminSea Voyages, a premium boating experience departing from the scenic shores of Montauk aboard a 2011 Steiger Craft Miami Cuddy Cabin.
Branford (2 hr 54 min drive from Southold)
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.
+1
4.8
/5
(86 external reviews)
Montauk (1 hr 33 min drive from Southold)
Step aboard the legendary CUJO, a beautifully restored 1977 Bertram Sportfish Sportfishing yacht, now better than ever after a full 2025 refit.
+2
5.0
/5
(1 review)
Montauk (1 hr 34 min drive from Southold)
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.
"Tony’s was a wonderful host. Knowledgeable, kind, and focused on providing the best trip possible." — Tim,
"Tony’s was a wonderful host. Knowledgeable, kind, and focused on providing the best trip possible." — Tim,
