Block Island Charters & Private Yacht Cruises
Block Island, NY
Block Island is the big crossing. It sits out in the open water of Block Island Sound, about fifteen miles past Montauk. This Rhode Island island is reachable only by boat or a small plane. A Block Island charter with Charters in The Hamptons is our longest and most special trip. We run it on a larger boat, with a licensed captain who handles the crossing for you. Go for a long day, or stay overnight for a real getaway. Either way, you arrive by private yacht, not packed onto a ferry.
What makes the Block Island trip different
This isn't a quick harbor cruise. Block Island sits across open water, in a different state, and the run is a real ocean passage. That's exactly why it's worth doing with a captain. The Sound can turn from glass to chop in a hurry, and fog rolls in fast out there. A USCG-licensed captain watches the weather window and picks the calm day. We're one of the private yacht charters in the Hamptons built for a run this long. We make the crossing on a larger, capable boat, never a small rental.
Most people see Block Island from the deck of a crowded ferry on a fixed schedule. You'll see it from your own boat, on your own time.
Day trip or overnight
You have two ways to do it. A long day trip gets you across, gives you the afternoon on the island, and brings you home by evening, weather permitting. An overnight turns it into a getaway. You cross over, settle into the Great Salt Pond, and spend the evening and the next day on the island. Then you head back on a calm morning. The overnight also takes the pressure off the weather. Some groups pair the crossing with a Montauk day trip on a separate calm day.
Will the crossing make you seasick?
Here's the straight answer. The open run across the Sound is bumpier than a calm bay cruise. But we only go on a settled day, so the ride is far smoother than a ferry stuck on a fixed schedule. A few things help. Eat light before you board. Take motion-sickness medicine an hour ahead if you are prone to it. Stay up on deck and keep your eyes on the horizon. Tell your captain if you feel off, and he can ease the ride.
Arriving in the Great Salt Pond
Boaters come to Block Island for the Great Salt Pond, the big protected harbor on the island's north side, also called New Harbor. On a busy summer weekend, hundreds of boats fill the pond. The town moorings are first come, first served, and they fill up fast. So your captain plans ahead. He can book a marina slip in advance, or get you there early and hail the harbormaster for an open mooring. Either way, you skip the stress of circling for a spot. Over on the east side, Old Harbor is the island's main village, with the ferry dock, the shops, and the restaurants.
What to do on the island
Block Island runs on bikes and mopeds. Most visitors leave the car behind and take the rolling roads on two wheels. Here's what's worth your time:
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The Mohegan Bluffs, dramatic clay cliffs on the south shore, with a long stairway down to the beach and a clear-day view back to Montauk.
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The Southeast Lighthouse, a National Historic Landmark perched right on top of the bluffs.
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The North Light, a granite lighthouse out at Sandy Point on the island's quiet north tip.
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Fred Benson Town Beach, the island's long, easy beach on the east shore.
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The Greenway Trails, winding through open conservation land. The Nature Conservancy named Block Island a Last Great Place, and nearly half of it is kept wild.
If your group likes to fish, the waters around the island are known for striped bass. We can fold fishing charters into the trip.
Why a captained charter, not a rental
For a trip like this, the captain is the whole point. With a self-rental, you'd handle the open-water navigation, the fog, and the docking yourself, and most rentals won't let you take a boat this far anyway. With us, you need no experience and no license. Once you know your group size and dates, you can view our fleet of charter yachts and pick the right boat for the crossing.
Planning your Block Island trip
A few honest notes, because this trip takes planning. We stage the trip from our Shelter Island home dock and run east from there. This trip lives and dies by the weather, more than any other we run, and your captain has the final say. Because the run home needs its own calm window, an overnight gives you the most flexibility. Tell us early if Block Island is on your list, so we can watch the forecast and book ahead. The Great Salt Pond fills up in peak summer, so the sooner we plan, the better your spot.
Planning your Block Island trip
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Bring your own food and drinks for the crossing. A cooler is welcome.
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Pack sunscreen, soft-soled shoes, and a layer or two, since it can be breezy out on the open water.
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For an overnight, bring a small bag, and we'll sort out whether you stay aboard or book a room on the island.
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We provide USCG life jackets for everyone aboard.
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Traveling with kids? Children under 13 must wear a life jacket while the boat is moving, unless they are below deck. We carry the right sizes.
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A word on weather: we don't sail in unsafe conditions, and that matters most on the Block Island run. If your captain calls it off, you won't lose your money, and we'll move the trip to the next good day.
What a Block Island charter costs
This is our longest trip, so it sits at the top end. Pricing depends on the boat, the day or overnight choice, and the season. We give you an upfront quote, with no hidden fees. You're paying for a capable boat, a licensed captain who can read the crossing, and a trip most people only do by ferry.
Frequently asked questions
Book your Block Island charter
Ready for the trip most people only take by ferry? Book a Block Island charter and let a licensed captain handle the crossing, the mooring, and the weather. Call (631) 251-1777 or fill out the inquiry form. We'll find a good window, the right boat, and a plan for your day or overnight on Block Island.
