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Offshore fishing aboard the Osprey refers to deep sea fishing the waters south of Long Island and Block Island, where the water depth increases. Offshore Fishing Charters 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 Charters 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. Inshore Fishing Charters provide the most consistent action while still having the possibility of landing trophy fish.

Call Capt. Jay directly to book your charter:

(860) 227-6922

Conditions at sea are subject to change.

Call for the most up to date info!


A specified deposit amount is required upon booking. Any remaining balance is due the day of the trip. There is a 10 day cancellation policy to any trip. If a cancellation is made 10 business days prior to the departure day and time, there is no outstanding fee. If a cancellation is made within 10 business days of departure day and time, the customer will be billed a 50% balance of the cost of the charter. If you do not cancel, this results in a no-show client and you will be billed the full cost of the charter. Canceling due to inclement weather is up to the Captain’s discretion. If the captain cancels due to weather the trip will be rescheduled. All sales are final.


To continue running the charters you are accustomed to, I must, unfortunately, implement a fuel surcharge for the foreseeable future. When fuel is over four dollars there will be an added surcharge. Thank you for being so understanding; this is obviously out of my control but necessary for me to continue to offer the best charters on the east coast.

When you book your fishing charter from CT, MA, RI or NY you will be fishing with one of the hardest working full-time Captains in the fleet. Below you will find directions to Osprey Sportfishing Charters.



Watch a video of Osprey Fishing Charters:


Send us your questions or get started booking your Sportfishing Connecticut, Rhode Island, New York or Massachusetts Charter trip! Phone calls are preferred as it is easier for Captain Jay to talk while sailing. Call the Captain directly at (860) 227-6922.

Please call before 8:00 pm EST, as the Captain has to wake up early for his trip in the morning.

6 Passenger Charter Vessel | All Prices are for the full boat (up to 6 passengers)

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