Written by Capt. Jeff Werner
July 2014

The Atlantic Ocean flows to the west from Block Island Sound to create the estuary called Long Island Sound. Every year, this “inland sea” gives boaters a summer full of cruising opportunities. At the eastern end of Long Island Sound, where the set and drift of the strong currents of The Race and Plum Gut test one’s navigation skills, is the Fishtail. Long Island is one hundred miles long (hence the name), and its eastern tip when viewed on a chart resembles the tail of a fish.

Mystic Seaport, Connecticut

As a young boy growing up on the streets of Brooklyn, weekend trips to Mystic Seaport with my father instilled in me love of the sea and maritime history. Today, the Seaport still draws crowds with “sea fever” and a strong desire to learn about our country’s maritime heritage. Mystic Seaport (860-572-5391, mysticseaport.org) also has its own marina with transient docks, and admission to the museum is included in your dock fee. Brewer Yacht Yard at Mystic (860-536-2293, byy.com/Mystic) is also a great place to tie up offering a full service boat yard, onsite swimming pool, laundry and shower facilities.

Day 1: Greenport & East Hampton, New York

Plan on an early start down the Mystic River to cross the narrow end of Long Island Sound. Enter the North Fork of the Fishtail at Plum Gut between Orient Point and Plum Island. Once in Gardiners Bay, cruise westward keeping Shelter Island to port. You will soon arrive at Greenport, your first stop after your 30 mile morning cruise. Spend the late morning and early afternoon ashore exploring the village of Greenport, which was named one of Forbes’ Prettiest Towns in America. Tie up your vessel right in town at Mitchell Park Marina (631-477-2200, villageofgreenport.org) and have lunch at Claudio’s Clam Bar or Claudio’s Crabby Jerry’s along the town wharf.

After a short siesta, fire up your engines and double back into Gardiners Bay. This time keep Shelter Island to starboard. Three Mile Harbor is your destination, 12 miles away on the south shore of the bay. Three Mile Harbor is a well protected body of water located “three miles” from East Hampton. Both Halsey’s Marina and Gardiner’s Marinas (631-324-5666, sea-incorp.com) offer 10% off dockage for Marinalife members throughout the summer.

Just east of the harbor is the hamlet of Springs, whose name probably does not ring a bell. However, the names of the Jackson Pollock, Willem de Kooning, Kurt Vonnegut, Joseph Heller, Phillip Roth, John Steinbeck and Nora Ephron may. These artists and writers have all worked or lived in nearby Springs. Although culturally important, Springs doesn’t have the draw of East Hampton. Most boaters just take the short taxi ride into town to shop and to have dinner at one of the tony restaurants. Perhaps you’ll spot David Geffen who just paid over $50 million for his
East Hampton estate.

Day 2: Sag Harbor & Riverhead, New York

After staying up to the wee hours with the young and hip in the East Hampton night club scene, you are probably
tempted to sleep in late, and have a latte delivered to your boat. Feel free to indulge, as your next port of call is Sag Harbor for lunch only 10 miles to the west. Most of Sag Harbor village is a national historic site which focuses on its prominence as a shipping and a whaling port from the 1790s to the 1860s. Enjoy a walking tour of the town after lunch, check with the tourist information center at the windmill at Long Wharf. Dock at Sag Harbor Yacht Club (631-725-0567, sagharboryc.com) just a short walk from town.

After departing Sag Harbor and rounding North Haven Peninsula, cruise southwesterly across Noyack Bay leaving the needle tip of Jessup Neck on your port side. Continue down Little Peconic Bay to Robins Island. Head north around the island through the North Race into Great Peconic Bay, and keep an eye out for shoals. Carry on across Great Peconic Bay, to Flanders Bay and continue up the Peconic River. This afternoon leg is about 25 miles, and you can tie up for the night at Treasure Cove Resort Marina (631-727-8386, treasurecoveresortmarina.com) in Riverhead offering Marinalife members 10% off transient dockage. The hamlet of Riverhead is the center of Long Island wine country and has almost 50 vineyards and wineries in the surrounding area (during the summer season the marina offers a daily shuttle service to local areas).

Day 3: The South Shore of the Peconic Bays & Shelter Island, New York

In the morning, cruise back out flanders Bay into Great Peconic Bay, round Red Cedar Point and continue eastward along the south shore of the bay for some gunkholing. In succession, explore the back waters of Red Creek Pond, Cold Spring Pond and Sebonac Creek and North Sea Harbor. If you have a stand up paddle board or sea kayak on board, drop your anchor and see what you can discover.

Continue northeasterly to Shelter Island in the afternoon, and the entrance to West Neck Harbor off Shelter Island Sound. The harbor has a designated anchorage area at southern end, or call ahead for a slip for the night at The Island Boatyard & Marina (631-749-3333) at the northern end. Either have dinner and dessert at the nearby Island Cafe, or just relax on the hook after a great day of cruising, sipping a glass of Long Island pinot noir. This picturesque island has five harbors to explore, each with its own unique flavor. You will be tempted to stay for more than a day. Stop by Sunset Beach (631-749-2001, sunsetbeachli.com) and drop anchor and enjoy drinks at the lively beachside restaurant and bar.


Capt. Jeff Werner has been in the yachting industry for over 25 years. In addition to working as a captain on private and charter yachts, both sail and power, he is a certified instructor for the USCG, US Sailing, RYA and the MCA. He is also the Diesel Doctor, helping to keep your yacht’s fuel in optimal condition for peak performance. For more information, call 239-246-6810, or visit MyDieselDoctor.com. All Marinalife members receive a 10% discount on purchases of equipment, products and supplies from Diesel Doctor.