Sailing Long Island Sound

Cuttyhunk, Block Island, Thimble Islands

Written by Franks Kok, Marinalife member since 2002

For the past ten seasons my wife, Mary, and I have owned Remedios, a Hinckley Southwester 59. We love the water and the boat, and we have sailed her all over the Eastern Seaboard—through the southern Chesapeake Bay, up to Newfoundland, even as far away as Bermuda. Every summer we try to identify the most undiscovered cruising grounds and then head there, but of course this keeps getting harder and harder. For several years we explored Maine, and then went even farther north, to Nova Scotia, an area that is beautiful and seriously uncrowded. Last year we decided to revisit the Long Island Sound and were pleasantly surprised by the trip. We realized that with a little advance planning we could still have unique experiences and find hidden gems, even with the destination being so popular. Here, we recount visits to some of our favorite harbors and anchorages during that voyage.

Cuttyhunk Island

Located at the southwestern-most point of the Elizabeth Islands, Cuttyhunk marks the eastern end of Long Island Sound and the southern end of Buzzards Bay. It is a delightful little island, one square mile in size, and only has about 50 permanent residents. In the summer the population swells to more than 400, but last year we got there on June 16, before the full season kicked in, and the atmosphere was still very placid. When we’ve visited the island before we’ve always chosen to overnight on one of the moorings in the outer harbor, but since we arrived early in the season those weren’t in place yet, so we sailed through the narrow channel to Cuttyhunk Pond instead. Once inside, boats are protected 360 degrees. The pond’s depth is 9 to 11 feet at low tide, and there’s no place to anchor, but there are plenty of moorings, all of which are managed by the Cuttyhunk Marina on a first-come, first-served basis. Simply tie up on an empty mooring and someone will swing by to collect the fee. If you’re lucky and the weather is reasonably nice, the raw-bar boat will arrive between 5 p.m. and 7 p.m., offering fresh oysters shucked by bikini-clad young women. The gent who manages the raw bar is a marketing genius. I don’t think that any of the boat owners who order oysters notice how much they’re paying for them—though their wives probably do. The marina also has slips that can be reserved in advance and accommodate boats to 100 feet, and several pilings in the harbor that are available for rent. Over the years, Marinalife has been very helpful in making our reservations at Cuttyhunk Marina.

To go ashore you can dingy to the southeastern end of the pond, where there’s a dock with an ice cream seller and a T-shirt shack on it. Best of all there’s also a fishmonger, who opens for business at 4 p.m. and sells whatever is fresh—lobsters (always), striped bass (probably, the waters around Cuttyhunk are famous for big stripers) and other local delicacies. Sometimes there are sport fishermen cleaning their catch on the dock, and they’re usually willing to part with some of their bounty for a modest remuneration, or even to make a gift of it. Don’t miss a hike up Lookout Hill, which has great views of the pond and the outer harbor.

Block Island

Approximately 35 NM from Cuttyhunk

“The Block,” as locals call it, lies about 14 miles east of Montauk Point and 13 miles south of Judith Point. The year-round population of 1,000 grows to 15,000 during the summer. It’s usually a charming place, especially in the off-season or during the week, but on this trip we arrived on July 5th. Big mistake. We’d hoped that, since it was a Monday, most of the Fourth of July partyers would have already left for home. No such luck. The place was packed, the barbecues were fired up, and the beer was flowing freely. All the marinas were at capacity and the harbormaster was too harried to help us find a mooring or a place to anchor. And to top it all off, it was blowing a stink. I do not want to detail how we finally found a mooring because we probably violated some regulation or law. I’ll just say that once you’re inside the Great Salt Pond, an extremely well-protected harbor with a depth of 25 to 50 feet of water, there is a reasonable chance of anchoring a bit north of the mooring field.

When you visit Block Island during the height of the season, you pick and choose your battles. The island is stunning and worth exploring for that reason alone, but you’ll also find yourself getting fed up by the piss-poor quality of service in the many restaurants and bars. If you’re a boater cruising Long Island Sound, though, you have to stop at the Block at some point, otherwise your friends will wonder what is wrong with you. It is a must-do destination, and can be completely captivating, just don’t expect peace and quiet. And remember that the harbormaster controls most of the moorings, but does not accept reservations for them. The Block Island Boat Basin will take bookings and Marinalife can really help with this. Whatever you do, be sure to plan ahead—dockage is at an absolute premium during the season.

Thimble Islands

Approximately 60 NM from Block Island

The Thimbles are an archipelago sprinkled just off the coast of the tony Stony Creek section of Branford, Connecticut. The islands are made of lovely pink granite and have many sheltered anchoring places. There are moorings, but none of them seem to be rental buoys. Holding ground is reasonable, and many boaters stop in the area for lunch. We’ve spent many nights here between the rocky islands and have always found the anchoring solid, even in inclement weather.

Most of the islands are either uninhabited or dotted with private summer homes. An occasional tourist boat makes the rounds, but there’s not much going on other than that. It is possible to dingy ashore to the town of Stony Creek, which has a small market, but this is not a major provisioning center. The Thimbles are a wonderful place to relax for the afternoon and night, but after that you’ll want to get going again.

Three Mile Harbor

Approximately 35 miles from the Thimble Islands

Three Mile Harbor makes an excellent alternative to Block Island on those weekends when the Block is just too full. The harbor is tucked inside Gardiner’s Bay, on the north side of Long Island’s South Fork, and is completely protected. The depth is about 20 feet throughout, but when you’re entering it make sure you pass red nun #22 before turning to starboard—it’s a long motoring passage from the bay into the harbor, and even after you think you’ve left the channel there’s still a sandbar along your starboard side until you’re completely past red nun #22. There are several marinas in the harbor, including Gardiner’s and Halsey’s; both usually have plenty of transient slips and moorings, even on holiday weekends.

Once ashore you can walk to East Hampton along a footpath beside Country Road 40, which turns into Main Street in East Hampton. Halfway to town, you’ll find a small grocery store on the left-hand side. You cannot miss it because there is almost always a traffic jam in the tiny parking lot. It’s expensive, but the shelves are full of all kinds of unique items, and it’s a good place for a special treat. If you continue on you’ll arrive at the IGA grocery store, where you can pick up pretty much anything you need. If you find yourself with too many bags to walk back to the harbor, the store will call a cab for you. And don’t miss a stroll around East Hampton—with all its high-end, Gucci-type stores and the like, it will give you plenty to talk about with your friends over a glass of wine once the cruising season has finished.