Southold Boat Tours
The best out of 16 boat tours in Southold - enter dates to check availability
25 ft
Up to 6 persons
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
Trips from
US $500
41 ft
Up to 6 persons
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.
Trips from
US $750
53 ft
Up to 10 persons
Sag Harbor (1 hr 16 min drive from Southold)
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.
Trips from
US $3,200
35 ft
Up to 6 persons
5.0
/5
(183 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.
Trips from
US $795
41 ft
Up to 6 persons
Montauk (1 hr 34 min drive from Southold)
Experience timeless elegance and adventure aboard Montauk Venture Charters, a beautifully restored 1961 Hatteras Sportfish Motor Yacht, fully refreshed in 2020.
Trips from
US $300
36 ft
Up to 6 persons
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.
Trips from
US $540
32 ft
Up to 6 persons
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
Trips from
US $550
28 ft
Up to 6 persons
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.
Trips from
US $450
40 ft
Up to 6 persons
5.0
/5
(19 external reviews)
Hampton Bays (13.1 miles from Southold)
Sea Venture is a 2025 Topaz 40 Royale Sportfish based out of Hampton Bays. It can take up to six guests. The boat is powered by two 500 HP diesel inboard Detroit Diesel engines, offering a maximum cruising speed of 25 knots.
Trips from
US $600
50 ft
Up to 27 persons
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.
Trips from
US $750