Port Chester Boat Tours
The best out of 27 boat tours in Port Chester - enter dates to check availability
36 ft
Up to 6 people
Windward Sailing Charters
5.0
/5
(3 reviews)
Oyster Bay (59 min drive from Port Chester)
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
40 ft
Up to 10 people
Charter Nirvana
Mamaroneck (5.1 miles from Port Chester)
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
50 ft
Up to 13 people
Long Island Yacht Rentals – Tranquility
5.0
/5
(1 review)
Oyster Bay (59 min drive from Port Chester)
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
20 ft
Up to 3 people
Viking Fly Charters
5.0
/5
(4 external reviews)
Norwalk (15.1 miles from Port Chester)
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
25 ft
Up to 6 people
Cast Net Charters
New
5.0
/5
(19 external reviews)
Island Park (27.8 miles from Port Chester)
Step aboard “GO FISH”, a 1987 Pursuit 2550 Center Console Cuddy Cabin operated by Cast Net Charters and based out of Island Park—perfect for unforgettable days on the water for up to 6 guests.
trips from
US $500
37 ft
Up to 6 people
Gypsy Soul Tours
New
Stamford (7.3 miles from Port Chester)
Gypsy Soul Tours offers private, custom sailing charters from Stamford, Connecticut, delivering unforgettable experiences on the scenic Long Island Sound.
+2
trips from
US $750
31 ft
Up to 6 people
Carolann P Fishing Charters
5.0
/5
(8 external reviews)
Freeport (25.7 miles from Port Chester)
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
44 ft
Up to 6 people
North River Sailing – Tantara
New
New York City (12.7 miles from Port Chester)
We’re setting sail across Long Island Sound this season from our home base on historic City Island.
trips from
US $600
30 ft
Up to 10 people
GO With The Flo Charters
5.0
/5
(1 review)
Wantagh (25.7 miles from Port Chester)
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
56 ft
Up to 13 people
Osca Yachting
New
Port Washington (12.0 miles from Port Chester)
Step aboard the 2025 Galeon 560 Fly and experience New York Harbor like never before.
+1
trips from
US $3,500