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We have five terrific options for your New York, Massachusetts, or Connecticut Inshore 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 Fisher’s 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. 


Note: Prices listed are for the full boat (upto 6 passengers)

Half Day Trip | 5 hrs | $820

Our Half Day trips leave the dock at either 4:30 AM, 10:00 AM or 12 Noon. 5 hours, more often than not, is ample time to catch your limit of fish and enjoy being out on the water. Our most common request is to catch Striped bass, though some customers enjoy catching a mix of both Stripers and Blues. Some also prefer to spend their day Fluke fishing. 


Full Day Trip | 7 hrs | $950

Our Full Day trips leave the dock at 4:30 AM or 10:00 AM. During the week, sailing times may be tailored to accommodate your party depending on already scheduled trips. The Full is similar to the Half Day, it just offers greater options and flexibility. More time often results in more fish, of course that is not a guarantee. We have an excellent reputation of sending our customers home with their limit of fish. The extra time may also allow for different types of fishing. 


Extended Day Trip | 10 hrs | $1,050

This is a fun trip for the group that may want to spend their morning fishing, make a stop over to Orient Point to have lunch in one of the many reputable restaurants, then finish out their day with another round of fun-filled fishing. The additional time also allows for Multi-Species options. 


Sunset Trip | 3 hrs | $500

This trip runs from 5:00 PM to 8:00 PM. It is a fun, beautiful way to fish, while watching the sun set over LI Sound. 


October Bass Trip | 9 hrs | $1,250

There is usually a Fall-Run of nice size Bass off Montauk at this time of year. This trip leaves the dock at 6:00 AM. 



Call Capt. Jay at (860) 227-6922 today to discuss the details of your New York, Massachusetts, or Connecticut inshore charter fishing trip. Phone calls are preferred since it is easier for the Captain to talk while sailing.

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

Fish the waters of Long Island Sound and Fisher's Island Sound…

Fish the deep waters south of Long Island and Block Island…

A thoughtful and unique way to say goodbye to a loved one...



Watch a video of Osprey Fishing Charters:

Send us your questions or get started booking your In-Shore Fishing 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.

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

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