Jamesport Charters on Great Peconic Bay
North Fork, NY
Jamesport is where the North Fork starts to feel like the North Fork. You have left the Riverhead sprawl behind, the road narrows, and the bay shows up on your right. A Jamesport charter is the easiest way to get onto that water without owning a boat or towing one. We run captained trips with USCG-licensed captains and pick up in Greenport, further east on Route 25. Our captains have more than 200 charters behind them on this bay. Call (631) 251-1777 and we will build the day around your group.
Where Jamesport sits on the water
South Jamesport is the waterfront end of the hamlet, and it sits at an interesting spot. This is where Great Peconic Bay and Flanders Bay meet, in the area local boaters call Hawk’s Creek. It is the far western corner of the Peconic system.
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That position has a practical consequence. You are a long way from the inlets and the open ocean, which is why this end of the bay is usually the calmest water on the East End. It is also a long way from the good fishing and the better cruising, which is why our trips start further east.
Meeting the boat
Our home dock is 63 S Menantic Rd, Shelter Island, NY 11964. Our North Fork pickup point is Greenport, which is a drive east on Main Road through Mattituck, Cutchogue and Southold. It is the longest drive of any North Fork hamlet we serve, and we will be straight with you about that.
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What you get in exchange is a much shorter run on the water to the parts of the bay worth seeing. If we picked you up in Jamesport you would spend a large part of your charter simply getting east. Sag Harbor is our other pickup option if your group is coming from the South Fork.
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A standard charter runs about four hours, with half-day and full-day trips available.
What the day looks like
From Greenport you are immediately in the wide, deep part of the bay. Shelter Island is right there. The Sag Harbor shoreline is across the water. Open water toward Gardiners Bay is within reach on a longer trip.
The contrast with the Jamesport end is the point. Up west the bay is shallow, narrow and quiet. East of Greenport it opens up, and that is where the charter experience actually lives.
Trips Jamesport charters run most
Full-day runs. If you are driving from Jamesport anyway, a full day makes the trip worth it. Our full-day charters cover more of the East End.
Fishing. Peconic Bay inshore trips for fluke, porgies, bluefish and black sea bass. Offshore trips with more notice. See our fishing charters page.
Sunset cruises. Roughly 90 minutes before sundown, two to three hours on the water.
Dock and dine. Dinner across the bay, boat there and back. Restaurant slips on the East End are first come, first served, so we plan around that.
Family days. Anchoring, swimming and a calm afternoon. The most requested trip we run.
Practical details
Six passengers plus crew is the cap, under the USCG six-passenger rule for uninspected vessels under 100 gross tons.
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Children under 12 must wear a USCG-approved life jacket while the boat is underway, on vessels 65 feet or under, under New York Navigation Law. Children inside an enclosed cabin are excepted. We provide approved life jackets for everyone.
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Bring your own food and drinks, plus towels, sunscreen and soft-soled shoes.
Why book Jamesport charters with us
We are cousins who grew up in the marina business on Shelter Island. Our captains earned their USCG licenses in 2019 and have run more than 200 charters. Being based in the middle of the Twin Forks means we reach both shorelines fast.
We run a fleet of 27+ vessels, from smaller boats for a family afternoon up to our flagship Pershing yachts. That range is the reason we can match a boat to the day rather than the other way round. The fleet page shows what is available.
Making the drive worth it
We would rather be straight with you than sell you a short trip. Jamesport is the furthest west of the North Fork hamlets we serve, and the drive to Greenport is real.
Groups that get the most out of it do one of three things. They book a full day rather than a standard four hours. They combine the charter with something else out east, a winery afternoon or dinner in Greenport. Or they split the group and have the South Fork contingent meet us at Sag Harbor instead.
Any of those turns the drive into part of the day rather than an obstacle in front of it.
Weekdays are quieter on the water and easier for parking.
Call (631) 251-1777 and we will price your date.
When your group is split across both forks
This comes up constantly, and it is one of the few logistics problems we can actually solve rather than just describe.
Half the group is staying on the North Fork. Half is in Sag Harbor or East Hampton. Meeting up on land means somebody drives an hour, or waits for a ferry, before the day even starts. Most operators run from one location and leave you to sort it out.
We pick up at two. Greenport on the North Fork and Sag Harbor on the South Fork. For a split group that means both halves drive fifteen or twenty minutes instead of one half driving an hour.
There are two ways to run it. Everyone meets at whichever pickup is fairer on the driving, which is usually Sag Harbor if the South Fork contingent is larger. Or, on a longer charter, we collect one group and then the other, which costs you some water time but no driving.
Tell us where everyone is staying when you call. We will tell you which version is faster. It is a better conversation to have before you book than after.
Frequently asked questions
Book a Jamesport charter
Jamesport charters reward a longer booking. Call (631) 251-1777 or email captain@chartersinthehamptons.com with your date, group size and pickup preference.
