How do you scratch the adventure sailing itch when air travel is challenging and a worldwide pandemic restricts entry to some countries? To paraphrase Dorothy Gale, you don’t need to look any farther than your own back yard. Close-to-home charters are often overlooked for exotic destinations farther afield but there’s great sailing to fun places to be had just a car ride away, and there’s never been a better time to explore.

The Northeast

Nantucket Island

 Trying to describe bareboat chartering in the Northeastern United States is like the classic parable about the blind men trying to describe an elephant by touching just one part. There are so many different “faces” to the Northeast that many skippers have spent a lifetime exploring these waters and still haven’t scratched the surface. 

The coastline and islands of New England are rich in maritime history. Pilgrims and whaling ships plied these waters, and the area is marked by picturesque harbors and a sophisticated charm. There’s no better starting point than Newport, Rhode Island, with its long yachting history, bustling harbor and Colonial streets that balance the Beaux Arts “summer home” mansions of the Wall Street barons. 

Just 15 miles offshore is Block Island with its single village (rent a bike to explore).  Don’t leave before the boat from Aldo’s Bakery makes the rounds of the anchorage, or you’ll miss fabulous pastries. Another 25 miles is Martha’s Vineyard, with resortlike Edgartown and more traditional Vineyard Haven. You can explore the Elizabeth Islands and then head for Cape Cod and the Massachusetts coast, with famed ports such as Marblehead 

and Gloucester. 

In no time, you’re in Maine, which old sailors called “Down East.” Rugged and serrated, a charter on this coast is like stepping back in time. Lobster fishing and boatbuilding are traditions in the small mainland and island towns and, even in the summer tourist season, life continues at a quiet and relaxed pace. You could spend your entire charter poking around Penobscot Bay, which has the picturesque ports of Camden and Rockport. From Penobscot Bay, you can exit via Eggemoggin Reach next to Deer Island and then head for Mount Desert Island.