Sunset over the Connecticut River with a small charter boat underway

Connecticut River · Long Island Sound

A river you already know,piloted by someonewho knows the rest of it.

One private boat. Six guests, never more. Three decades of coves, lighthouses and golden-hour water that never shows up on the chart.

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From $400 · Docking Fees Included

41°23'N 72°26'W

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USCG 100-Ton Master40,000+ Sea MilesSix Guests, Never MoreDocking Fees IncludedLate May — Mid NovemberDeep River, ConnecticutUSCG 100-Ton Master40,000+ Sea MilesSix Guests, Never MoreDocking Fees IncludedLate May — Mid NovemberDeep River, Connecticut

“Everyone finds the main channel. The good stuff is a hundred yards off it.”

Captain Lawrence Stewart · Deep River, CT

01Signature Charters

Three ways to spend a day on the water

Every charter is private, every price is the whole price, and every route bends to whatever the light is doing that evening.

02The Route

Deep River to the Sound, the long way

We leave from Kirtland Street and work south — through Selden Neck's back channels, past Essex, out the river mouth at Saybrook and, on the long days, all the way to Ledge Light.

DEEP RIVERDeparture · 134 Kirtland StSELDEN NECKHidden coves, shallow draftESSEX HARBORSunset turnaroundSAYBROOK LIGHTRiver mouthLEDGE LIGHTLong Island Sound41°23'N · 72°26'W — SOUNDINGS IN FEET AT MEAN LOW WATER
The teak helm of the Gypsy Soul

Limestone 24

At the Helm

Captain Lawrence Stewart

USCG 100-Ton Master with commercial towing and sailing endorsements. Over 40,000 sea miles logged, and thirty-plus years working out the moods of this particular river — its hidden coves, its history, and where the ospreys are nesting this season.

40,000+
Sea Miles
30+
Years Local
100-Ton
Master Licence
03Aboard

What's already on the boat

No add-ons, no fuel surcharge at the dock. Bring food and whatever you'd like to drink; the rest is waiting for you.

  • Cushioned bow & cockpit seatingSix Guests
  • Cups, plates and utensils aboardProvided
  • Bottled water, soda and iceProvided
  • Towels and blankets for the run homeProvided
  • Bring your own food and drinksWelcome
  • Every docking fee on the routeIncluded
04Guests Aboard

What people say when they step back off

“
We've lived in Essex twenty years and saw four places from the water we didn't know existed.

Meredith K.

Sunset Cruise · August

“
He timed the whole run so we hit the lighthouse right as the light came on. That's not luck.

Dan & Priya R.

Lighthouse Run · July

“
Cold drinks, blankets when it got breezy, and nobody rushing us. Felt like a friend's boat.

The Alvarez Family

Full Day · September

Guests aboard the Gypsy Soul at dusk
Season 2026

The light is best about an hour before it goes.

Late May through mid-November. Sunset dates go first — tell us yours and we'll confirm within a day.

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