Captain Skippy on the Long Island Sound holding a striped bass in front of a lighthouse

Meet Captain Skippy

USCG-licensed. Local-born. Twenty years on this water.

Captain Skippy is a licensed 50-ton Master and OUPV (six-pack) charter captain, with over twenty years of fishing experience in the Central Long Island Sound. The credentials are the paperwork — the real value is the time on the water. He's run more trips out of Mount Sinai than he can count.

His charter operation is built around one belief: a small, private boat with a captain who actually knows the water beats every head-boat experience by a country mile. You won't share rail space with strangers. You won't be rushed off the boat. You'll fish where the fish actually are — because Skippy knows.

USCG 50-Ton Master CaptainHigher-tier credentialing for inland & near-coastal waters
USCG OUPV (Six-Pack) endorsementAuthorized to carry paying passengers
20+ seasons on the Central LI SoundMount Sinai, Old Field, Crane Neck, Shoreham, Stratford Shoal, Smithtown Bay
Fully insured commercial charterCoverage on hull, liability, and passenger
The Christina M II — a 26-foot Hunter Scott Pilot Cove Down East fishing boat at the Mount Sinai dock

The boat

Christina M II — a 26-foot Down East built for the Sound.

The Christina M II is a 1998 Hunter Scott Pilot Cove Down East. It's not the flashiest boat on the water — it's better than that. It's the right boat for what we do. The hull cuts through the Long Island Sound chop. The cockpit layout gives 4 anglers real fishing room. The cabin keeps you warm when the wind picks up, and the cabin has a functioning head (bathroom) on board. And the trolling motor lets us hold on tough drifts when conditions go sideways.

26-ft Hunter Scott Pilot Cove · 1998Classic Down East hull — handles the Sound's short, steep chop
Minnkota trolling motorQuiet hold over structure when wind & current fight
Modern electronicsSonar, GPS & chart plotter to dial in the structure
Rigged for 4 (5 case-by-case)Real fishing room in the stern. Not a head-boat rail.
Full USCG safety equipmentPFDs, VHF, flares, first aid

Where we fish

The Central Long Island Sound, by heart.

Every captain says they know the water. Ours has the logbook. From Mt. Sinai we work the structure of the central Sound — close enough that you fish more, run less.

Mount Sinai Harbor & mouth

Sand flats, ledges and rock clusters right outside the inlet — great fishing close to home, productive on tide changes for stripers and bluefish.

Port Jefferson & Old Field

Just west — ledges and structure that hold striped bass, fluke and porgies all spring.

Rocky Point, Shoreham & Wading River

The shoals and ledges to the east — some of the best fluke and porgy grounds in the Sound.

The Middle Grounds & CT side

When the weather allows — deeper water and rocky ledges hold stripers all summer long, while deep wrecks hold big blackfish and sea bass.

Come fish with someone who actually knows this water.

$150 deposit. Easy to book. Easier to remember.

Call SkippyBook a trip