Cutchogue Charters
North For, NY
Cutchogue is farm country that happens to touch the bay. Most people who come out here spend the weekend on Route 25, moving between wineries and farm stands, and never see the harbor at all. A Cutchogue charter fixes that. We run captained trips with USCG-licensed captains, and we pick up in Greenport, a short drive east. You leave the car once and spend the afternoon on Peconic Bay instead of in it. Our captains have run more than 200 charters in this water. Call (631) 251-1777 and tell us your date.
Where you meet the boat
We do not keep a dock in Cutchogue. Our home dock is at 63 S Menantic Rd, Shelter Island, NY 11964, and our North Fork pickup point is Greenport. From Cutchogue that is a straight run east on Main Road, past Southold, into the harbor village.
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If part of your group is staying on the South Fork, we can pick up at Sag Harbor instead. Groups split across both forks are common out here, and we would rather sort the logistics on the phone than have you guess.
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A standard charter runs about four hours. Half-day and full-day trips are available too.
Cutchogue Harbor and the water south of town
Cutchogue’s water is on the bay side, tucked into Cutchogue Harbor and the creeks that feed it. This is protected water. When the wind is up and Long Island Sound is unpleasant, this stretch usually stays workable.
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Robins Island sits just offshore in Great Peconic Bay, privately owned and undeveloped. Boaters see a side of it that road traffic never does. Downs Creek runs inland from the harbor, and the Fort Corchaug archaeological site sits along it. The fort was built by the Corchaug people, and Cutchogue takes its name from them. The site was listed on the National Register of Historic Places in 1974.
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On shore, the Old House on the Village Green dates to 1649 and was listed on the National Register in 1966. Cutchogue also planted what is generally credited as Long Island’s first commercial vineyard in 1973, which is why the wine map out here starts where it does.
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We point these out as we go. You are not getting a lecture, but if you want to know what you are looking at, our captains know.
Trips Cutchogue charters run most
Swim and anchor days. The harbor and the back creeks are calm enough to drop anchor and let people get in the water. This is the trip families book most.
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Fishing. Inshore trips in Peconic Bay target fluke, porgies, bluefish and black sea bass through the warm months. Our Hamptons fishing charters cover each trip type in detail.
Sunset runs. Peconic Bay faces southwest from the North Fork shoreline, so evening light out here is the main event. We push off roughly 90 minutes before sunset.
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Dock and dine. We will run you across the bay for dinner and bring you back. Restaurant slips on the East End are first come, first served, so we time the trip around that.
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Group celebrations. Bachelorette groups, birthdays and small corporate days all run out of the same pickup. Our full destination list shows where those trips can go.
Rules that shape your trip
We carry up to six passengers plus crew. That is the USCG six-passenger rule for uninspected vessels under 100 gross tons, and it is federal, not a house policy.
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Under New York Navigation Law, children under 12 wear a USCG-approved life jacket while the boat is underway on vessels 65 feet or under. Children inside an enclosed cabin are excepted. We carry approved life jackets for every person aboard.
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Bring food and drinks. A cooler is fine. Towels, sunscreen and soft-soled shoes are the rest of the list.
Who you are booking Cutchogue charters with
We are cousins. We grew up in the marina business on Shelter Island, which sits in the middle of the Twin Forks, and we have been running these harbors since long before it was a business. Our captains earned their USCG licenses in 2019 and have more than 200 charters behind them.
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We run a fleet of 27+ vessels, from smaller boats for a family afternoon up to our flagship Pershing yachts. That range is why we can match a boat to the day rather than the other way round. The fleet page shows what is available.
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Being based in the middle matters more than it sounds. From Shelter Island we can reach Cutchogue Harbor, Greenport, Sag Harbor and the open bay quickly. You are not spending your first hour getting somewhere.
Wine country, from the other side
Cutchogue planted what is generally credited as Long Island’s first commercial vineyard in 1973. Fifty years on, the hamlet sits at the center of the North Fork wine map, and most visitors experience it entirely by car.
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A boat changes the shape of the day. Groups often do tastings in the morning, meet us in Greenport in the afternoon, and finish on the water. It is a better sequence than the reverse, for reasons we probably do not need to spell out.
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Call (631) 251-1777 and we will price your date.
The six passenger limit, and what to do about it
This is the single most common thing groups run into on the East End, and most charter websites bury it. We would rather put it up front.
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Almost every private charter boat out here carries a maximum of six passengers. That is not a preference and it is not about boat size. Under federal rules, an uninspected vessel under 100 gross tons may carry no more than six passengers for hire, regardless of how many people would physically fit aboard. A 50 foot boat and a 30 foot boat sit under the same cap.
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So if you are planning a bachelorette weekend for twelve, or a birthday for sixteen, you will hit this wall at every operator you call. Groups who research it usually get discouraged before they book anything.
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What actually works is running more than one boat. We can put two boats out together, matched on speed, meeting at the same anchorage or the same restaurant dock. It takes more planning and it needs more notice, especially in July and August. It is also the only honest way to do a large group on private charter boats on this bay.
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Call before you build the guest list, not after. We will tell you what your number means in boats.
Frequently asked questions
Book a Cutchogue charter
Cutchogue charters run through the warm months and weekend slots go first. Call (631) 251-1777 or email captain@chartersinthehamptons.com. Give us the date, the group size, and whether Greenport or Sag Harbor is the easier pickup for you.
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