The Northeast coast of the U.S. has a well earned reputation for being one of the finest, most varied and largest cruising grounds in the world. From the sandy shores of Long Island Sound and Cape Cod all the way east to the ironbound remoteness of Roque Island, the region offers hundreds of harbors and gunkholes and the opportunity to explore famous yachting havens like Newport, Marblehead, Portland and Camden.Along this coast, there are dozens of marinas and marine service yards where sailors can leave boats between cruises and have repairs and upgrades performed by professionals with a long Yankee tradition of boat building and yacht maintenance. There are too many gems of harbors along this coast to include in one article, so we will highlight 20 that we know and love and can recommend to cruisers who will be chartering or cruising along the amazing Northeast coast.1. Thimble Islands, CT: A collection of 365 granite islets of which only 32 are habitable, the Thimble islands just off Branford, CT, look like a piece of Maine dropped into the sandy shoals of the sound—which is what they are since they were deposited here by glaciers as the Ice Age retreated. On a calm summer night, the Thimbles offer several good anchorages where you can swing peacefully, but you need accurate charts and tide tables because the islets are strewn with ledges and home to strong tidal currents. The village of Stony Creek has supplies and fuel.2. Port Jefferson, NY: Port Jeff on the Long Island shore has a large secure harbor that offers protection from weather in all directions. You can anchor off the main channel fairly near town or you can pick up a mooring or tie up in a marina for a fee. Just inside and east of the harbor entrance, Mt. Misery Cove is a great little gunkhole with a nice beach on the sound. But the cove will be crowded on weekends at the height of the summer season. Port Jeff is a tourist town as well as a yachting center, so there are plenty of shops, galleries, ice cream stands and restaurants. Once a ship building center, Port Jeff has a long maritime history and a quaint old section of town dating back to the 18th Century.3. Fishers Island, NY: Although tucked up against the Connecticut shore east of the Connecticut River, Fishers Island belongs to New York State. Long the summer home of some of America’s wealthiest families, Fishers Island is mostly gated private estates but does offer a good anchorage, a small village and some great routes for hiking and biking and exploring the beaches. West Harbor on the island’s north coast is the best anchorage in all but strong northerlies. The holding is good and there is a dinghy dock at the head of the harbor. A great place far from the madding crowd, Fishers Island is a lovely and exclusive retreat.4. Mystic, CT: The best reason to sail to Mystic is to visit Mystic Seaport up the Mystic River at the north end of town. The entrance to the river at Noank is on Fishers Island Sound and leads between shallows up a well marked channel. There are marinas available just inside the river mouth, or you may opt to cruise upriver and through the draw bridges to moor at Mystic Seaport itself—you’ll need a reservation. Mystic Seaport is a living maritime museum where employees wear traditional 18th Century garb as they build and repair classic wood boats and ply trades such as glassblowing and barrel making. The seaport is home to the classic whaling ship Charles W. Morgan, which is now undergoing a massive rebuild.5. Shelter Island, NY: On Long Island’s North Fork, you will find a series of shallow bays and dozens of good and even great anchorages and gunkholes. Shelter Island is among the best since it offers several good anchorages and pleasant and picturesque walks ashore. Dering Harbor on the island’s west side is a yachting center where you will find an inspiring collection of classic and modern sailing and motor yachts. Ashore, good restaurants are within walking distance of the harbor. On the island’s south side, Smith Cove and Major’s Harbor provide secluded anchorages well protected from northerlies. The real gem of Shelter Island is Coecles Harbor on the northeast side; totally landlocked and blessed with white sand beaches, the harbor has a fairly shallow entrance, so beware during strong easterlies.6. Block Island, RI: Block Island, which lies due south of Point Judith, is the perfect New England getaway. You enter the Great Salt Pond or New Harbor via a narrow, dredged cut. The pond offers excellent protection from weather and has good holding for the anchor in sand. Moorings and marina slips are available. Once anchored or moored, you will have plenty of exploring to do, from the long stretch of white sand on the northeast tip to the high cliffs and beaches on the southern and southwestern side. The village, a short walk from Salt Pond, offers good restaurants and bars. It’s easy to kick back and spend a few days at Block enjoying the rustic scenery, laid back locals and far-from-it-all ambience.7. Newport, RI & Narragansett Bay: Newporters like to call their city by the sea the sailing capital of the U.S., a boast hotly disputed by other cities. But Newport and the Bay are indisputably a great cruising destination. In summer, you’ll find a diverse fleet of boats with flags of foreign nations on many sterns. Newport has an amazing array of restaurants, shopping, music festivals and sporting events. Up the bay, Wickford, Bristol, East Greenwich and Barrington make interesting stopovers; the Kickamuit River is a good hurricane hole. No matter from whence you hail, sailing into Newport is like sailing into home waters. This is where sailors live.8. Cuttyhunk, MA: The westernmost of the chain of the Elizabeth Islands in southern Massachusetts, Cuttyhunk is a hilly little island with a large secure harbor that is positioned at the intersection of Buzzard’s Bay and Vineyard Sound. The outer and inner harbors have mooring balls to pick up and there are good anchorages—larger boats outside and smaller boats inside. The island is rustic and harkens back to a different century since there are no cars and few amenities. But it is a great place for a beach barbecue and a long hike over the hills to capture the amazing vistas of Martha’s Vineyard and the Elizabeths. You are apt to see deer grazing, osprey nesting and acres of rosa regosa clinging to the hillsides. A great place to catch your breath and commune with nature.9. Hadley Harbor, MA: At the eastern end of the Elizabeth Islands, you will find Hadley Harbor just before the narrows at Woods Hole. Another peaceful anchorage that can get quite crowded in summer, Hadley Harbor is one of the best natural harbors around. The island is privately owned, so strolls ashore are frowned upon. Still, for a quiet interlude and a secure night’s sleep in an absolutely beautiful setting, Hadley Harbor has few equals. On quiet evenings you are sure to see deer browsing along the shore and sheep feeding on the hillside inland.10. Menemsha, Martha’s Vineyard, MA: A quaint fishing village that is far from the glitz and celebrity culture of Edgartown and Vineyard Haven, Menemsha is home to a working fishing fleet, a couple of seafood wholesalers, a couple of fish restaurants and that’s about it. The entrance from Vineyard Sound is a narrow cut through a white sand beach. Inside you will be directed to moor to floating docks or alongside another boat. Smaller boats with shallow drafts may opt to continue inland to Menemsha Pond, which is tucked in under the hills of Aquinnah and overlooked by summer cottages of various sizes. From Menemsha you can walk or bike across the island to the beautiful south beaches or climb to the lighthouse at Gay Head. For eating fresh seafood straight off the boats, Menemsha is the best harbor around.11. Vineyard Haven, Martha’s Vineyard, MA: The main ferry terminus and shipping port for the island, Vineyard Haven has a long storied tradition as a summer colony and a center for wooden boat building and repair. The outer harbor has a large mooring field and you can either rent a mooring or anchor out of the channel. The harbor is open to the north and northeast. The inner harbor lies behind a breakwater and is filled with moorings and many lovely restored sailing craft from ages gone by. In bad weather, you may be able to rent a mooring inside the breakwater. Ashore you are in the town of Tisbury, which is an eclectic place notable for enforcing the blue laws that prohibit the sale of alcohol. All of the restaurants are BYOB and, not surprisingly, there is a liquor store not far away just across the town line. Vineyard Haven is home to the Black Dog restaurant, famous for hats and T-shirts sold worldwide with their black lab logo on them.12. Edgartown, M.V., MA: Once a great whaling town and now one of the prettiest summer resorts in the Northeast, Edgartown has a large, secure harbor that opens up to the inland salt pond that is Katama Bay. You enter the harbor between a picture perfect lighthouse and a long white sandy beach. Inside, you will have to pick up a rental mooring if you want to be near town or you can anchor half a mile away at the southern end of the mooring field. The town is filled with historic homes and buildings from the golden age of whaling, while the harbor is ringed by mansions and summer “cottages” from every golden age since. Martha’s Vineyard has long attracted an affluent intelligentsia from New York and Boston, so the island has the air of being well preserved, well funded and politically correct. The shopping is excellent, the restaurants are the best on the island and the walks and biking routes interesting and lovely.13. Nantucket, MA: Twenty-two miles off Cape Cod, Nantucket is one of the most famous cruising destinations along the northeast coast. Once a leading whaling port that generated fortunes in the first half of the 19th Century, the island has deep maritime traditions. The waters around Nantucket are crisscrossed with shoals, so you need to navigate carefully and with the latest charts. Inside the harbor you will find slips in the excellent marina or mooring balls for rent, or you may opt to anchor outside the mooring fields. Beware of the shallows to the east and south. If you want to anchor out of the main harbor, there is enough depth for most cruisers in the first bay to the east inside Coatue Pt. off a white sand beach. Boats with drafts under five feet can explore the shallow eastern bay all the way to Head of the Harbor. Nantucket has become a serious tourist destination and is summer home headquarters for the CEO set. The mixture of t-shirt buying throngs and the exuberance of all that stock option cash has transformed the island from a quaint and charming seaport into “Nantucket Land.” Still, the island is beautiful, charming and well worth a visit.14. Boston, MA: With all of the lovely harbors to the north and south of the city, Boston is often overlooked as a port of call along this coast. That’s too bad. Boston Harbor, once one of the filthiest in the nation, has been cleaned up and has a very active sailing community. At the head of the harbor in Charlestown, you will find two large marinas where you can pick up slips for a few days; these are gated and have security. Ashore, Boston is an easy town to explore on foot or by public transportation and offers lots of history, museums, galleries, restaurants and culture.15. Marblehead, MA: Like Newport, Marblehead is a sailor’s harbor in the extreme. Home to legendary sailors like Ted Hood and Robbie Doyle and host to some of the biggest summer regattas as well as the start to the Marblehead-Halifax Race, this little crowded harbor has a very special allure that has drawn sailors for generations and is home to the Eastern, Corinthian and Boston Yacht Clubs. You will need to pick up a mooring or rent a slip since there is limited room to anchor. Ashore, you will find a quaint New England town, good restaurants and all of the marine services you might require.16. Portland and Casco Bay, ME: The city harbor at Portland and nearby Falmouth Foreside make for a good starting point for a cruise east along the Maine Coast. You will find secure anchorages, moorings and slips to rent. Ashore, the little city of Portland has gone through a revival and has a pleasant arty atmosphere, good restaurants and a vital waterfront. You will find professional boatyards here where you can undertake repairs or leave your boat for a while or the winter. Sailing east of Portland you have all the intricacies of this jagged, ragged coast to explore including the Kennebec River, Boothbay Harbor, the Damariscotta River, Muscongus Bay and Thomaston up the beautiful St. George River.17. Camden and Penobscot Bay, ME: The town of Camden, with its open harbor and rocky coast, is one of Maine’s oldest summer colonies and home to a vibrant yachting scene and excellent repair facilities. Using Camden as a base, you have before you the magnificent Penobscot Bay with hundreds of small islands, amazing gunkholes, charming villages and historic harbors. Some of the gems in Penobscot Bay include Pulpit Harbor, the Fox Islands of North Haven and Vinalhaven, the Barred Islands, Castine and Bucks Harbor. But, there are dozens more that will enchant you for weeks or even years. Penobscot Bay is considered by many world cruisers to be one of the finest cruising grounds on the planet.18. Stonington, ME: At the tip of Deer Isle on the eastern shore of Penobscot Bay, the village of Stonington is a special stopover. The harbor is full of working craft instead of yachts and the village is a pure Maine experience that has somewhat vanished from the tourist towns and summer colonies of Camden, Boothbay and Mt. Desert Island. This is a lovely, somewhat untouched region of the coast where you will find dozen of pine-topped rocky islets, snug coves, clear water and very few other cruisers. In Stonington, you can buy lobster and other seafood in the local shops that is as fresh as any you will find in any region and the heavy Maine accent spoken by the locals will be just as authentic.19. Mt. Desert Island, ME: Sailing toward Mt. Desert Island with the afternoon sun illuminating the hills and craggy mountain tops is as fine a sight as a cruiser will see. The island is home to Acadia National Park and three famous summer colonies at Southwest, Northeast and Bar Harbors. It is also home to world famous yacht builders Morris Yachts, Hinckley Yachts and Jarvis Newman. Favorite anchorages around the island are in Southwest Harbor and up the fjord-like inlet at Somes Sound. In Northeast Harbor you have to rent either a slip or a mooring. The villages at Southwest and Northeast Harbor are charming and have good eateries, ice cream stands, art galleries and markets. Hiking the national park offers some of Maine’s best vistas. You could easily spend a happy week cruising around and exploring the island.20 Roque, Island, ME: A goal of many East Coast sailors, Roque Island is a destination worth enduring the fog, extreme tides and cold water to achieve and is often the farthest east a cruiser will get during a summer’s cruise of the Maine Coast. The anchorage is large and open to the east. Oddly, the western side of the harbor has a lovely white sand beach, rare Downeast, off which you can anchor. In easterly weather, you can anchor in Shorey Cove or tuck into tiny Lakeman Harbor for protection. The island is privately owned, but visitors can walk the trails and climb the hills for exercise and great views. In summer, eagles and osprey can be seen tending their young.