Ossining Boat Tours
The best out of 21 boat tours in Ossining - enter dates to check availability
28 ft
Up to 6 people
Dinner on a Yacht - the Hudson River
Croton-on-Hudson (2.8 miles from Ossining)
Step aboard Gypsy Rose Yacht, a beautifully restored 1981 Cruisers Yachts VillaVee 288 Cruiser (fully renovated in 2025), and experience the thrill on The Hudson River.
trips from
US $1,300
36 ft
Up to 6 people
Windward Sailing Charters
5.0
/5
(3 reviews)
Oyster Bay (26.3 miles from Ossining)
Sail Long Island's Gold Coast aboard a beautifully maintained 2012 Jeanneau Sun Odyssey 36i.
"From the start, Jonathan was both a gracious host and a skilled, knowledgeable captain." — Todd,
"From the start, Jonathan was both a gracious host and a skilled, knowledgeable captain." — Todd,
+5
trips from
US $525
20 ft
Up to 3 people
Viking Fly Charters
5.0
/5
(4 external reviews)
Norwalk (24.3 miles from Ossining)
Viking Fly Charters is a classic 2008 SeaCraft center console based in Norwalk, offering private, customizable trips for up to 3 guests.
+1
trips from
US $295
31 ft
Up to 6 people
Carolann P Fishing Charters
5.0
/5
(8 external reviews)
Freeport (39.4 miles from Ossining)
Carolann P Fishing Charters is a beautifully restored 1998 Luhrs 31 Sportfishing vessel (restored in 2025), based in Freeport, offering an unforgettable maritime experience for up to six guests.
+1
trips from
US $500
50 ft
Up to 13 people
Long Island Yacht Rentals – Tranquility
5.0
/5
(1 review)
Oyster Bay (26.3 miles from Ossining)
Yacht rental includes watersports. Step aboard Long Island Yacht Rentals, a luxurious 2001 Carver 466 Motor Yacht, beautifully restored in 2025 and based in scenic Oyster Bay.
"Captain Jeff was great, the boat was great, the water activities activities were great." — Joyce,
"Captain Jeff was great, the boat was great, the water activities activities were great." — Joyce,
+1
trips from
US $1,800
40 ft
Up to 10 people
Charter Nirvana
Mamaroneck (16.3 miles from Ossining)
Step aboard Nirvana, a timeless 38’ Pearson 386 sailing yacht, and experience the beauty of Long Island Sound without the crowds, just you, your guests, and the open water.
+2
trips from
US $440
46 ft
Up to 12 people
Ocean Breeze Yacht Rental llC
4.3
/5
(1 review)
New York City (39.7 miles from Ossining)
Experience luxury and adventure with Ocean Breeze Yacht Rental LLC aboard this stunning 2006 Meridian 411 Sedan Bridge, based in New York City.
"Captain Andy was great, particularly with all of the kids." — Duncan,
"Captain Andy was great, particularly with all of the kids." — Duncan,
trips from
US $1,900
36 ft
Up to 6 people
Rockaway Charters
5.0
/5
(2 reviews)
•
288 external reviews
New York City (39.8 miles from Ossining)
Set sail on a luxurious and unforgettable adventure with Rockaway Charters, a 1999 Luhrs 36 Open Sportfishing boat that has been meticulously restored in 2024 for your comfort and enjoyment.
trips from
US $550
30 ft
Up to 10 people
GO With The Flo Charters
5.0
/5
(1 review)
Wantagh (39.9 miles from Ossining)
GO With The Flo Charters is a beautifully restored 2001 Pursuit 3070 Offshore Center Console (refit in 2026), delivering the perfect mix of performance, comfort, and reliability.
"Been going out with Capt Rich for years and ALWAYS have the best time." — Luie, New York
"Been going out with Capt Rich for years and ALWAYS have the best time." — Luie, New York
+3
trips from
US $800
44 ft
Up to 6 people
North River Sailing – Tantara
New
New York City (22.6 miles from Ossining)
We’re setting sail across Long Island Sound this season from our home base on historic City Island.
trips from
US $600