Osprey Fishing Charters is family owned and has been delighting fishermen from New York, Massachusetts, and Connecticut for over 50 years. Capt. Jay is U.S. Coast Guard licensed with 28 years of experience fishing the waters of Eastern Long Island Sound, Montauk and Block Island.


The boat is a 38 foot, custom-built Harris, powered by a Cummins diesel engine. The spacious cabin is very clean, comfortable and heated to give our customers a pleasant experience aboard the Osprey. Whether you are an expert or a first time fisher, our team will show you a fishing trip to remember, guaranteed. 


When you book your trip from New York, Massachusetts, Rhode Island or Connecticut, you will be fishing with one of the hardest working full-time Captains in the fleet.


For more information on our fishing charters, or to book your outing, please contact us today.

Phone calls are preferred call Capt. Jay directly at (860) 227-6922.

Offshore fishing aboard the Osprey refers to fishing the waters south of Long Island and Block Island, where the water depth increases. Offshore trips are a minimum of 12 hours, as it takes more time to get to and from the fishing grounds. This is a much different experience than Inshore fishing in that it requires greater patience and an ability to withstand rough waters. For those willing to gamble and seek a thrill of a lifetime at the expense of consistent fishing of smaller species, this trip is for you. The larger oceanic fish such as Shark, Tuna, Marlin and Swordfish are large, beautiful, strong and often put up an acrobatic fight when hooked. If you are willing to take the chance at having this amazing experience, then this trip is for you!

Charter Fishing experience. This includes half, full, and extended day trips as well as a sunset trip and an October Bass Trip. Inshore fishing aboard the Osprey refers to the waters of Long Island and Fishers Island Sounds. Fish most prevalent in these waters are Striped Bass, Bluefish, Fluke, (Summer Flounder), Black Fish and Porgie, in season. Inshore fishing is a fun experience for both the beginner and the experienced fisherman, as our first mate is there to instruct and assist if needed. This type of fishing provides the most consistent action while still having the possibility of landing trophy fish.

A thoughtful and unique way to say goodbye, the Osprey offers Burials at Sea. We offer an affordable, private and dignified scattering of ashes and memorial service of up to two hours. The sea offers a tranquil and poignant resting place for a loved one, especially for those who loved the ocean in life. Whenever you look upon the water, you can remember your dearly departed knowing they are adrift in the current.


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Send us your questions or get started booking your Connecticut, Rhode Island, New York or Massachusetts Charter trip! Phone calls are preferred call Capt. Jay directly at (860) 227-6922.

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6 Passenger Charter Vessel