Orient Charters and Orient Harbor Boat Trips
North Forth, NY
Orient is the end of the road. Route 25 runs out at the ferry dock and the land stops. Everything past that point is water, and it is some of the most demanding water on the East End. An Orient charter is how you see it without having to handle it yourself. We run captained trips, every captain holds a USCG license, and we pick up in Greenport. Our captains have more than 200 charters on this water. Call (631) 251-1777 and tell us what you want the day to be.
Plum Gut, and why it matters
The gap between Orient Point and Plum Island is called Plum Gut. It is deep, it is narrow, and on an ebb tide the current through it runs over five knots. Oyster Pond Reef extends from Orient Point about a third of the way across, just under the surface. It is a genuinely serious piece of water and it has a reputation among mariners for a reason.
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Standing at the end of Orient Point you can watch it move. From a boat with a captain who knows the tide tables, you can see it properly and safely.
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Orient Point Lighthouse sits out in the Gut. It was built in 1899, it is a cast iron sparkplug tower about 64 feet tall, and local mariners have called it the Coffee Pot for generations. It was added to the National Register of Historic Places in 2007. It is still an active aid to navigation.
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We are honest about this: not every trip goes through the Gut. Conditions decide, and the captain decides. Ask when you book and we will tell you what is realistic for your date.
Where to meet us
Our home dock is 63 S Menantic Rd, Shelter Island, NY 11964. Our North Fork pickup point is Greenport, which from Orient is a drive west on Main Road through East Marion. It is a short run.
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Sag Harbor is available as a South Fork pickup. A standard charter is about four hours, with half-day and full-day options.
Orient Harbor and the water around it
The harbor is the protected water on the bay side, south of the village. It is calm, it is shallow at the edges, and it is completely different in character from the Gut a couple of miles north.
Orient Beach State Park runs out along the spit that forms the harbor’s southern edge. From the park you can see four lighthouses, and the state park is a US Lighthouse Society passport stamp location for that reason. From the water you get the same view without the walk.
The Orient Historic District, listed on the National Register in 1976, covers Village Lane and the surrounding streets. It is one of the best preserved stretches of old village on the East End, and the view of it from the harbor is the one most visitors never get.
Trips Orient charters run most
Sightseeing runs. Orient Harbor, the state park shoreline, and the lighthouse view if conditions allow.
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Fishing. The water east of Orient is where the bay fishing turns into open-water fishing. Our Hamptons fishing charters page covers inshore and offshore trips.
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Sunset cruises. Roughly 90 minutes before sundown, two to three hours out.
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Longer eastern runs. Full-day trips can push toward Gardiners Bay and beyond. Our destinations page shows the range.
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Family afternoons. Anchoring and swimming in the harbor, which stays calm when the Gut does not.
What you should know
We carry six passengers plus crew. That is the USCG six-passenger rule for uninspected vessels under 100 gross tons, and it is federal.
Under New York Navigation Law, children under 12 must 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 everyone aboard.
Bring your own food and drinks, towels, sunscreen and soft-soled shoes.
Why book Orient charters with us
We are cousins who grew up in the marina business on Shelter Island. Our captains earned USCG licenses in 2019 and have more than 200 charters behind them. Out here, knowing the tide is not a nice-to-have. Plum Gut punishes guessing.
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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 the reason we can match a boat to the day rather than the other way round. The fleet page shows what is available.
Working around the ferry
The Cross Sound Ferry runs between Orient Point and New London, Connecticut, and it is the only vehicle ferry across this part of the Sound. That traffic crosses Plum Gut on a schedule, and it is a significant factor in how we route trips at this end of the fork.
Our captains give way and plan around it. It is one more reason the eastern water rewards a licensed captain over a rented boat and a chart app.
Call (631) 251-1777 and we will price your date.
How far east you can actually get
Orient is the jumping-off point, and this is where the difference between operators stops being about boats and starts being about range.
Most self-drive rentals on the East End come with a defined operating area, commonly bounded at Robins Island in the west and Gardiners Bay in the east. That box makes sense for a rental company managing risk. It also means the water past Orient is off the table.
Our captained trips are not bounded that way. On a full day we run to Fishers Island, and Block Island is within reach with the right boat, the right weather window and enough notice. Both sit well beyond where a rental will let you go.
Worth knowing about Fishers Island before you ask: there is no public ferry to it from Long Island. The Fishers Island Ferry District runs from New London, Connecticut only. Arriving by private charter is the practical way to get there from this side.
Range is not a boast, it is a planning constraint. If the trip you have in mind is east of Orient, say so on the first call, because it changes which boat we put you on and how much notice we need.
Frequently asked questions
Book an Orient charter
Orient charters reach further east than most. Call (631) 251-1777 or email captain@chartersinthehamptons.com. Give us your date, group size and pickup preference.
