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.
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
4.3
/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.
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,
