About Your Guide

Matt Casamassima

Independent Guide
Growing up along the North Shore of Long Island, Captain Matt has spent over 25 years fishing and clamming the waters of Long Island Sound. With deep roots in these waters and a lifetime of local knowledge, he brings unmatched experience and enthusiasm to every trip. Now a USCG-certified captain, Matt runs trips out of Cos Cob, Connecticut—perfectly positioned within 15 miles of the best fishing spots in the Western Sound.

Whether you're chasing trophy Striped Bass or loading up on tasty Tog, Captain Matt has a proven track record of putting anglers on fish. His passion for the sport and commitment to delivering top-tier experiences have made him one of the most productive captains in the area, season after season. If you’re ready to reel in some serious action and see what the Western Sound has to offer, Captain Matt is ready to take you there.

About Your Guide

Matt Casamassima

Independent Guide
Growing up along the North Shore of Long Island, Captain Matt has spent over 25 years fishing and clamming the waters of Long Island Sound. With deep roots in these waters and a lifetime of local knowledge, he brings unmatched experience and enthusiasm to every trip. Now a USCG-certified captain, Matt runs trips out of Cos Cob, Connecticut—perfectly positioned within 15 miles of the best fishing spots in the Western Sound.

Whether you're chasing trophy Striped Bass or loading up on tasty Tog, Captain Matt has a proven track record of putting anglers on fish. His passion for the sport and commitment to delivering top-tier experiences have made him one of the most productive captains in the area, season after season. If you’re ready to reel in some serious action and see what the Western Sound has to offer, Captain Matt is ready to take you there.
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Fishing Long Island Sound

NEW 1 - 6 People 8 Hours From $700
Full Day Bass Trip
Full Day Bass Trip
Full Day Bass Trip
Full Day Bass Trip
Full Day Bass Trip
Full Day Bass Trip
Full Day Bass Trip
Full Day Bass Trip
Full Day Bass Trip
Full Day Bass Trip
Full Day Bass Trip
Full Day Bass Trip
Full Day Bass Trip
Full Day Bass Trip
Full Day Bass Trip
Full Day Bass Trip
Full Day Bass Trip

About Your Trip

Water Type

Inshore, Nearshore

Skill Levels

Beginner, Intermediate, Advanced

Weather

You won’t lose your deposit if the trip is canceled due to weather

If you're looking to fish the inshore waters of Western Connecticut like a pro, Captain Matt is your guy. With a laser focus on trophy catches and a deep commitment to delivering a high-quality experience, Captain Matt’s inshore trips are your ticket to big fish and bigger memories on Long Island Sound.

From hunting down Trophy Striped Bass in the current to bouncing bucktails for Doormat Fluke or targeting Whitechin Tog (Blackfish) on gnarly structure,...

About Your Trip

If you're looking to fish the inshore waters of Western Connecticut like a pro, Captain Matt is your guy. With a laser focus on trophy catches and a deep commitment to delivering a high-quality experience, Captain Matt’s inshore trips are your ticket to big fish and bigger memories on Long Island Sound.

From hunting down Trophy Striped Bass in the current to bouncing bucktails for Doormat Fluke or targeting Whitechin Tog (Blackfish) on gnarly structure,
Captain Matt doesn’t just put you on the water—he puts you on the bite. These trips are designed for anglers who want to get dialed in and fish with purpose, whether you're a seasoned saltwater vet or brand new to the game.

You’ll be fishing from a custom-built 28’ Terry Jason, powered by a 400HP IVECO diesel that gets you to the fish fast—often running up to 25 miles to stay ahead of the pack. Outfitted with top-of-the-line Garmin, Lowrance, and Furuno electronics, this rig is locked in on fish-holding structure and designed for comfort and capability in any conditions. With a pilot house heater, dual anchor system for precise bottom fishing, and full USCG safety gear, you're covered from every angle.

Captain Matt spares no detail when it comes to gear. You’ll fish with custom rods hand-built by Captain Neil, matched to Penn and Avet reels for the perfect balance of strength and sensitivity. Whether you’re jigging shallow wrecks with Tidal Tail jigs for Tog or working Spro bucktails for Fluke, your setup will be dialed for success. All bait and tackle are included, and at the end of the trip, your fish will be cleaned, bagged, and iced—so you can go from deck to dinner table with zero hassle.

Parking is available, making arrival easy and stress-free. Just bring your snacks, drinks, and a strong arm—because when that big one hits, you’re going to need it.

If you’re ready for a trip that’s all about big fish, top-tier tackle, and serious local expertise, Captain Matt is standing by to show you what inshore fishing in Western Connecticut is all about.
Amenities

Water Type

Inshore, Nearshore

Skill Levels

Beginner, Intermediate, Advanced

Tackle

All rods, reels, and tackle are included.

Fish Cleaning

This guide will clean your catch for you.

Beer

Feel free to enjoy responsibly, but please no glass.

Live Bait

Live bait is included for this trip.

Weather

You won’t lose your deposit if the trip is canceled due to weather

Flexible Cancelation

This trip can be canceled up to 14 days before the trip.

Boat Restroom

No, this boat does not have a bathroom on board.

Kid Friendly

This trip is not suited for small children.

Disability Friendly

This trip is not suited for those with disabilities.

Lunch

Please provide your own food / snacks.

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About Your Boat

Boat photo for Fishing Long Island Sound
Boat Type
Down East Cruiser
Boat Length
28'
Boat Restroom
No
Engine Manufacturer
IVECO

About Your Boat

Boat Type
Down East Cruiser
Boat Length
28'
Boat Restroom
No
Engine Manufacturer
IVECO
Total Horsepower
400
Number of Engines
1
Additional Amenities
Garmin 4212 Chart Plotter w/ Radar overlay Lowrance HDS Charter Plotter/Side Scan Furuno FCV587 8.4� Color sounder Icom VHF Marine Radio Viking 6 Man life raft, Epirb, All mandated USCG Safety Equipment Pilot house Heater Custom Dual Anchor System built by Bill Heath for wreck/bottom fishing
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Potential Target Species

Color-coded seasonality below is based on .
View Full Species Seasonality Chart »
  • Get it while it's HOT!
  • This species is in play.
  • You might get lucky (as long as things are in-season).
  • Couldn't tell ya! (no data)

Techniques

Artificial Lure Fishing
Bottom Fishing
Heavy Tackle Fishing
Light Tackle Fishing

Types of Fishing

Inshore
Nearshore

Need a Place to Stay?

Cos Cob Charters Photo Gallery

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Fishing Long Island Sound
May 21st, 2025
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Fishing Long Island Sound
May 21st, 2025
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Fishing Long Island Sound
May 21st, 2025
Cornwall, Connecticut
Fishing Long Island Sound
May 21st, 2025
Cornwall, Connecticut
Fishing Long Island Sound
May 21st, 2025
Cornwall, Connecticut
Fishing Long Island Sound
May 21st, 2025
Cornwall, Connecticut
Fishing Long Island Sound
May 30th, 2025
Cornwall, Connecticut
Fishing Long Island Sound
May 21st, 2025
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Fishing Long Island Sound
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