Shelter Island Charters & Private Yacht Cruises
Shelter Island, NY
We're the charter company that's actually based on Shelter Island. Not a mainland operator who crosses over to pick you up. Our home dock sits right here at 63 S Menantic Rd, in the calm waters between the two forks. A Shelter Island charter with us means quiet creeks, easy sunsets, and a licensed captain who knows these waters by heart. No ferry. No crossing. Just step aboard and go.
Charters from our Shelter Island home dock
Most charter boats have to travel to reach Shelter Island. We start here. That central spot, right between the North and South Forks, means we can slip into the island's protected harbors and creeks within minutes of leaving the dock. Because we never have to cross over first, your charter time is spent on the water, not getting to it.
Charters in The Hamptons is run by cousins Mike Guanaco and JT McCarthy. They grew up in a boating family and worked as dockhands at their family's Shelter Island marina. Both earned their USCG captain's licenses in 2019, and they've run more than 200 charters since. When they say they know these waters, they mean it.
You can compare all our Shelter Island yacht charters and pick the trip that fits your group.
Back-creek eco tours, our specialty
This is what we're known for. A back-creek eco tour is a slow, quiet cruise into the protected creeks and coves around the island, where the water is calm and the wildlife is close.
Much of the route runs along Mashomack Preserve, the Nature Conservancy land that covers about a third of Shelter Island. Ospreys nest here, and you'll often see them overhead. We keep to a no-wake pace and stay clear of the nesting areas. The whole Peconic Estuary is a federal No-Discharge Zone, so clean, low-impact boating isn't just nice here, it's the rule. Our captains run these creeks with that in mind. On a calm morning the water turns glassy, and you'll often spot great blue herons and egrets working the shallows along the banks. It's about as far from a crowded party boat as you can get.
What you'll see on the water
Depending on your route, a Shelter Island cruise can take in:
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Coecles Harbor, a quiet, protected harbor ringed by undeveloped shoreline.
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Dering Harbor, the island's classic yachting harbor.
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West Neck Harbor, with its calm anchorage and waterfront tables.
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The Sylvester Manor shoreline, a working farm with roots going back to the 1650s.
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Sunset Beach and Crescent Beach, two of the island's best spots to watch the sun drop over the water.
Ways to charter
Pick the trip that fits your group:
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Sunset cruises. Catch golden hour over the water. Ask about our Shelter Island sunset cruises.
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Back-creek eco tours. Our signature quiet nature cruise into the creeks and coves.
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Family days. Calm creeks and easy water, with life jackets on board in every size.
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Engagement and bachelorette cruises. Private and captained for your big moment.
Fishing charters. Cast a line with a captain who knows the local spots.
Why a captained charter
You don't need any boating experience to come aboard. A USCG-licensed captain runs the whole trip. That's a big deal in these waters, where the creeks are shallow, the channels are narrow, and the no-wake and conservation rules matter. Our captains know where to go, where to anchor, and where to slow down. You just enjoy the ride, with no license to show and no big deposit to put down. Once you know your group size, you can choose your charter boat from our fleet.
Getting here without the ferry
For most visitors, Shelter Island is reachable only by ferry, the North Ferry from Greenport or the South Ferry from near Sag Harbor. If you're staying on the island, a charter from our home dock skips the ferry line entirely. If you're coming from the North or South Fork, we also offer ferry-free pickup points at Greenport and Sag Harbor, so you can meet the boat on your side of the water. A standard charter runs about 4 hours, with half-day and full-day options.
What to bring and good to know
Keep it easy:
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Bring your own food and drinks. A cooler is welcome.
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Pack towels, sunscreen, and soft-soled shoes.
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We provide USCG life jackets for everyone aboard.
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Traveling with kids? Under New York law, children under 12 wear a life jacket on boats under 65 feet while the boat is moving. The calm creeks make this an easy trip for families.
A word on weather: we don't sail in unsafe conditions. If your captain calls off the trip for weather, you won't lose your money, and we'll help you reschedule. Safety always comes first.
What a Shelter Island charter costs
Pricing depends on the boat you choose, how long you're out (a half day, the standard 4 hours, or a full day), and the season. Bigger boats and peak summer dates cost more. We give you an upfront quote before you book, with no hidden fees. A private captained cruise costs more than a small self-rental, but you get a licensed local captain, a boat sized to your group, and a calm day you don't have to steer.
Frequently asked questions
Book your Shelter Island charter
Ready to see Shelter Island from the water, the way the locals do? Book a Shelter Island charter from our home dock and let a licensed captain take care of the rest. Call (631) 251-1777 or fill out the inquiry form, and we'll match you to the right boat and the right cruise.
