With good winds from Maine to Block Island, New England is one of the best places in the world to be a sailor. Sailing, for all its mystique and jargon, is a New Englander’s inheritance—and it’s simple enough to learn without going broke or risking life and limb. There are numerous yacht clubs in Boston and its environs where you may learn the fundamentals of reading the wind, filling sails, and sailing the seas. New England is a state where you can learn how to sail but also discover many islands, bays, and cities along its long coastline. In this article, I will list the best boating destinations in New England so as to give you some ideas about which one you should choose. Keep reading!

Swan Island, Richmond, ME

There are multiple Swan Islands in Maine, but this one is located 10 miles north of Bath on the Kennebec River. Large forested regions are intermingling with open fields and marshes on the island, which is part of the Steve Powell Wildlife Management Area. Nature trails crisscross the island, and mountain biking is available on the main road. There are several ancient homesteads as well as an old cemetery to see. Kayaking or canoeing is the best way to get to the island and its state-run campground on the eastern side. Boaters are permitted to camp overnight, although advance arrangements are necessary. Note that the landing port on the island’s northwest tip is only for boats that pick up/drop off passengers or gear.

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South to Naushon and Newport, Rhode Island

Head south of Vineyard Sound to the small island of Naushon and then onto Newport, Rhode Island, for a voyage that blends one of New England sailing’s best-kept secrets with one of its most iconic centers. It’s a long way down the Cape, so stay a night at Duxbury before sailing through the Cape Cod Canal to Woods Hole. You can anchor in Tarpaulin Cove on Naushon, which is virtually fully undeveloped and owned by the Forbes family. Then, with a short sail to Newport, the region’s most famous yachting town, you’ll be back in civilization. It will be well worth the effort to call ahead for a slip at the Newport Shipyard & Marina.

Buzzards Bay, MA

Buzzards Bay, which stretches from Rhode Island Sound to Cape Cod and is bordered by the Elizabeth Islands, is home to a number of lovely harbors and plenty of island hopping. It is a terrific place to go cruising for a week, and despite the name, you won’t encounter any buzzards along the route. New Bedford, a historic whaling town, has a lot to offer cruising yachtsmen. It is home to one of the top whaling museums in the world. New Bedford Whaling National Historical Park is located in New Bedford, Massachusetts. Quissett Harbor is one of the most beautiful ports in the world, with walking trails down the shore, cute small boats on tightly strung moorings, and a golf course winding down to the harbor.

Hadley Harbor, second only to Quissett in terms of beauty, with enough area for a complete fleet to dock in the Forbes family’s back yard. It’s also a decent substitute for Wood’s Hole if you arrive at the incorrect time to deal with the Hole’s incredible currents. Cuttyhunk is one of the favorite NE Coast destinations since it is gorgeous, isolated, serene, and charming. It’s a real place with real people. Note that Buzzards Bay is known for having some of the most difficult boating waters on the east coast. The strong currents that surge through some of the islands’ cuts can be intimidating and even deadly if you don’t pay attention. But, when the sun shines and you respect the tide’s movement, you can have the time of your life and visit some of the most picturesque spots on the east coast.

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Chesapeake Bay, Maryland

The Chesapeake Bay is a genuinely lovely site along the United States coasts. It is by far the largest estuary in the country, with more shoreline than any other Bay. In fact, it has 11,600 miles of coastline, which is more than the total US coastline. It spans six states and drains 64,000 square miles. There is something for everyone, from the north, where the mighty Susquehanna flows down from Pennsylvania. And, to the west, where the port cities of Baltimore, Annapolis, and Washington DC stand along its tributaries. Also, to the east, where civilization has scarcely impacted the way of life in generations.

Much with the magnificent Chesapeake Bay Bridge-Tunnel bridging the huge stretch at the Bay’s mouth, the entire lower Chesapeake is even more distant. This means that most of the Chesapeake offer an unspoiled beauty that is difficult to conceive in these times. And, especially in such close proximity to such global concentrations of culture as the nation’s capital.

The Chesapeake Bay features a natural cruising route perfect for exploration. From the northern approaches, the C&D (Chesapeake and Delaware) Canal can be used to access the Chesapeake from Delaware Bay. This is a popular route for “snowbirds” traveling down the ICW to escape the chilly weather. Although it is possible to transit the full length of the Bay from dawn to sunset, the Chesapeake is set up as if it were meant for a leisurely hopscotch cruise from shore to shore.

Long Island Sound, CT

Long Island Sound is situated between Long Island to the south and New York/Connecticut to the north, and the two sides are vastly different in terms of topography and culture. The bays there offer a succession of wonderful sailing spots, while the northern territory is defined by rivers that flood surrounding islands that provide nighttime refuge. A beautiful site just off the banks of the great city of Greenwich is excellent for a day sail or an overnight stay on a calm summer night. This natural barrier to Greenwich Harbor and its environs is made up of three islands (Great Captain, Little Captain, and Wee Captain).

Hempstead Harbor, located almost directly across the Sound from Larchmont and Rye and the next harbor over from Manhassett Bay on Long Island’s North Shore, has a rich history. The Thimble Islands archipelago is a group of steep granite “islands” rising out of deep-sea, with jagged ledges and a few beautiful residences hidden among tall pines to the southeast of Branford, Connecticut. They are assumed to have been swept off the coast of Maine and brought to their current location by the glacier.

Lastly, the Connecticut River is fortunate in that it has a shoaling problem at its mouth. The River was never developed for industrial purposes because of the shallow shifting bars at the mouth. As a result, it has remained as immaculate as it was centuries ago. And, Essex at the first turn, Hamburg Cove, Selden Creek, East Haddam, and beyond, each town more attractive than the last, each harbor more serene than the other.

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Norwalk Islands, CT

For boaters in southern Connecticut, the Norwalk Islands are a terrific sailing destination. The 25 low-lying islands that make up the archipelago shelter Norwalk Harbor from high seas and bad weather while simultaneously providing a natural playground for boaters, fishermen, birders, beachgoers, etc. The town of Westport owns Cockenoe Island, which is open to the public. By late summer, the island’s tidy little cove and beach are teeming with snapper bluefish. Shea Island and the smaller Grassy Island to the east are managed by the Norwalk Recreation & Parks Department. Both are rocky, overgrown swaths of land. On these islands, seasonal camping is permitted with permission from the Norwalk Recreation and Parks Department.

Selden Island, Lyme, CT

The 607-acre Selden Neck State Park in Lyme, immediately across the town of Chester, is a must-see for boaters and paddlers on the Connecticut River. While the island does not have an official landing point, boaters can anchor just offshore or beach their boats on the banks. Approach with caution because there are submerged rocks at some portions of the shore. Some trails ascend to the 230-foot summit and past an old farmstead and quarry, while others wind through the wooded island. The Connecticut River may be seen from a number of vantage points along the paths. You should respect the boundary markings as certain areas of the island are still privately owned.

Selden Creek, which runs between the mainland and the island’s eastern border, is a lovely and well-protected place for birdwatching, SUP, and kayaking. However, larger boats can also transit the tranquil, reed-lined stream. Along the creek, keep an eye out for osprey, heron, egrets, kingfishers, hawks, beaver, muskrat, deer, and other animals. Note that autumn is a particularly beautiful time to visit this beautiful canal.

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Maine

Maine is a renowned sailing territory, with its rocky, jagged coastline, innumerable islands, abundant lobsters, and larger-than-life characters. Real people, real scenery, and real fog. The most famous itinerary takes you to Penobscot Bay, Blue Hill Bay, and Mt. Desert, among other places. And, between the boroughs of Rockland and Camden. The greatest month to sail in Maine is in August. It’s when the weather often creates a window in the fog, and the water begins to warm up.

Starting from Rockland Harbor, Burnt Coat Harbor, and Northeast Harbor you will enjoy the whole route. Then, McGlathery and Stonington where you can anchor in a serene setting. Lastly, Camden is a popular tourist spot on the coast of Maine. Camden is a breathtakingly gorgeous beachfront community known as “the place where the mountains meet the sea.” With white-steepled churches, tiny streets lined with quaint shops and restaurants, extensive parks and commons, and grand old mansions, it is one of New England’s most photographed harbors.

The New England Islands

Block Island is one of New England’s most popular boating locations. Block Island is a rustic island with a lot of natural beauty and Victorian charm. The island is known as the Bermuda of the North, and it’s a laid-back island with several prominent venues that are well connected by adequate roads. New Harbor (also known as Great Salt Pond) and Old Harbor, are where the town’s heart is.

Visit the Elizabeth Islands in Massachusetts, which stretch southwest from Cape Cod’s southern tip to Woods Hole. Cuttyhunk is the farthest island on the southern end of the island chain, and it is made up of a variety of islands and island groupings. The Elizabeth Islands, which are bordered on the north by Buzzard’s Bay and the south by Vineyard Sound, are located between the mainland and Martha’s Vineyard. They must be considered when passing to the north or south of these islands. This is because passing to the north requires passing through the strong current of Wood’s Hole, and passing to the south requires passing around the Sow and Pigs Reef. Lastly, don’t omit visiting Nantucket which is one of the most famous boating destinations in Massachusetts.