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Business Details
50+ Years
experience
Premier Charter Fishing Adventures in Connecticut
Osprey Fishing Charters has been delivering exceptional charter fishing experiences across Connecticut, Rhode Island, New York, and Massachusetts for over 50 years. Founded as a family-owned operation, our legacy is built on a deep passion for the sea and a commitment to providing unforgettable adventures for anglers of all skill levels. Captain Jay, a U.S. Coast Guard-licensed professional with over 40 years of hands-on experience, leads our team with expertise honed through decades of navigating Eastern Long Island Sound, Montauk, and Block Island waters. We pride ourselves on maintaining a 38-foot custom-built Harris boat equipped with state-of-the-art fishing gear, ensuring every trip combines comfort, safety, and productivity.

Our dedicated first mate provides personalized instruction, cleans and bags catches, and guarantees a seamless experience from departure to return. Whether pursuing trophy fish in offshore waters or enjoying consistent inshore action, clients benefit from our comprehensive knowledge of local fishing grounds and seasonal species. With a focus on transparency, we supply all necessary bait, tackle, and equipment while maintaining clear communication about weather conditions and trip logistics. Our reputation as one of the region's most experienced charter services stems from unwavering dedication to customer satisfaction and a genuine love for connecting people with the ocean's natural wonders.
Services
Offshore Fishing Inshore Fishing Burial at Sea Charter Trips Deep Sea Fishing Sunset Cruises Trophy Fishing Group Excursions Fishing Instruction Equipment Rental
Details
  • Year established: 1972
Highlights and features
  • We offer over 50 years of charter fishing experience across four states.
  • Our U.S. Coast Guard-licensed captain provides expert guidance and local knowledge.
  • We supply all necessary bait, tackle, and high-quality fishing equipment.
  • Family-owned operation with a proven track record of customer satisfaction.
  • Custom-built 38-foot vessel ensures comfort and safety during all excursions.
Services
Offshore Fishing
Venture into deep waters south of Long Island and Block Island for 12-hour excursions targeting large oceanic species. Our offshore trips cater to anglers seeking trophy fish like sharks, tuna, marlin, and swordfish. The experience demands patience and resilience against rougher conditions while offering thrilling battles with powerful marine life.
Inshore Fishing
Explore calmer Long Island and Fishers Island Sounds with half-day to extended excursions. Target seasonal species including striped bass, bluefish, fluke, and blackfish. Ideal for beginners and experienced anglers seeking consistent action with opportunities to land trophy catches in productive coastal waters.
Burial at Sea
Conduct dignified, private ash scattering ceremonies with up to two hours of dedicated vessel time. This service provides a meaningful oceanic resting place for loved ones, combining respectful memorialization with tranquil maritime settings to honor cherished memories.
People
Capt. Jay
Captain
U.S. Coast Guard-licensed captain with 28 years navigating Eastern Long Island Sound, Montauk, and Block Island waters. Specializes in delivering expert-guided fishing trips while maintaining safety and customer satisfaction standards.
Questions
How do I book a fishing charter?
Call Captain Jay directly at (860) 227-6922 before 8:00 PM EST. Organize a group of up to 6 passengers, make a deposit, and confirm trip details for immediate booking.
What's included in the charter service?
All necessary bait, tackle, custom-built rods, and high-quality reels are provided. Our first mate offers hands-on instruction, cleans catches, and ensures comfortable cabin facilities during trips.
What happens if weather conditions change?
Captain decides cancellations based on safety. Weather-related cancellations allow rescheduling. Trip status updates provided directly by phone before departure.
What areas do you serve?
We operate from Groton, CT, covering Long Island Sound, Block Island, Montauk, and surrounding waters across Connecticut, Rhode Island, New York, and Massachusetts.
What's the cancellation policy?
Full refund available for cancellations 10 business days prior. 50% charge applies for cancellations within 10 days. Weather-related cancellations receive rescheduling options.
Videos
Reviews (6)
Will Creedle
Nov 01, 2021 Report
Captain Jay and first mate Justin were fantastic. They sailed to a beautiful place, and we released our parents ashes there. They were thoughtful, understanding and patient. It made for a beautiful, I'd bittersweet day. Many thanks to them both.
Jamall Warren
Sep 03, 2021 Report
The crew is very punctual and professional. First mate Tucker made sure we had the best possible experience out at sea. From teaching us how to properly handle bait, equipment and fish, to learning how to clean and fillet the catch. He even taught us a better way to clean and cut porgy to get the best possible cut, the strips we got were excellent for fish tacos, so many of us are underinformed about the flavor and quality of porgy's, it was very helpful we will remember this trip for the rest of our lives. The captain brought us right to the fish everytime, very knowledgeable, he pretty much guaranteed
Anthony Epstein
Jul 26, 2021 Report
We had a tuna trip booked at osprey but the weather had different plans. Captain Jay went out of his way to make sure we still had a trip. We went out for bass.Caught some big fish!!!!
Jay is awesome, knowledgeable and extremely welcoming. His mate Justin is also Fantastic! Couldn't have asked for a better mate on our trip.
STELLAR EXPERIENCE ALL AROUND!!!!! This is our guy for all future trips.
Paula Pellerin
Jun 30, 2021 Report
We used their services to scatter ashes yesterday & were very pleased. Jay was easy to work with when I was trying to set this up, offering a great location to scatter the ashes. I'm far from a boat person & would prefer not to step on one at all, but both Jay & Tucker were professional (& sympathetic to my fears) & made the trip perfect. My family members were all very happy with the boat ride & the scattering was simple, yet fitting. And Jay even gave us the coordinates of where the scattering took place! I would wholeheartedly recommend The Osprey to anyone looking for a "burial at sea" option
Luis Matos
Jan 26, 2021 Report
Loved the experience very nice clean and well organized good coaching you will not live the boat with out the daily catch. Good boat crew please dont' forget to tip the skipper he works very hard.
Susan Larouche
Nov 14, 2020 Report
Went on my first charter fishing trip with family with Capt. Jay and it was amazing! I had NO idea what I was doing and both the Capt. Jay and the mate were great! Professional, personable, and made sure we enjoyed ourselves, left satisfied, and with a ton of fish! Definitely will be booking again in the future.