6 New England Boating Trips To Enjoy In 2026

Budding sailors prepare for a lesson aboard a classic 12 1/2 at the Herreshoff Museum.

The end of the year is certainly not a time when many New Englanders are boating. But it IS a time of year when New Englanders can dream about what their boating days might bring them in 2026.

Now is the time to start plotting next summer’s boating adventures, taking aim at those trips and experiences that will make your 2026 boating season the best ever.

Photo courtesy Newport Vineyards.

Here are a few boating ideas that are sure to make your new year a memorable one.

Bask In Beautiful Bar Harbor

The Maine coast is known for being a world-class cruising destination. But even in a state with as many incredible places as Maine has, Bar Harbor stands out. This famous resort port is home to stunning scenery, offers easy access to Acadia National Park, and provides visiting boaters with great food, interesting shops, and lots to enjoy. Learn more about Bar Harbor.

Dock & Wine At Local Wineries

The New England coast is home to more than just beautiful harbors and charming seaside towns. It’s also an increasingly popular region for wineries. In such boating hotspots as Narragansett Bay, Cape Cod, and the Connecticut coast, a handful of vineyards are perfectly positioned to allow boaters to create their own ultimate wine-lover’s cruise. Learn about six New England wineries you can visit by boat.

Discover Historic Bristol

Often overshadowed by its glitzier neighbor to the south, Bristol Harbor in Rhode Island is no slouch as a boating destination. Quite the opposite. Famous for being the “Home of Herreshoff,” Bristol has narrow, shady streets, an attractive village center, and wonderful shops and restaurants that make it Narragansett Bay’s yachtiest spot north of Newport. Learn about boating in Bristol.

Victory Point serves up a plentiful Lobster Roll.

Cruise To The Thimble Islands

Those arriving by land can only experience the Seuss-like Thimble Islands in Stony Creek, Connecticut for a few hours. But boaters can toss the hook in protected gunkholes and watch the singularly beautiful sunrises and sunsets that set these chunks of granite — ranging from several acres to boulder-size — ablaze with color. Learn about cruising to the Thimble Islands.

Dine At New England’s Dock & Dine Capital

If New England were to have a dock and dine capital, it would have to be Marina Bay in Quincy, Massachusetts. Not only is it a large, vibrant marina with more than 800 slips, easy access to Boston Harbor, and stunning views of the Boston skyline, but it is home to a massive collection of excellent restaurants, from high-class cuisine to family-friendly favorites to breweries. It’s a place where the worlds of boating and dining converge to form a destination like no other. Discover the many dock and dine options at Marina Bay.

Explore the Isles of Shoals

Located just five nautical miles off the rugged coastlines of New Hampshire and southern Maine, the Isles of Shoals are a great boating destination and a world unto themselves. The archipelago consists of nine little islands clustered off the coast, and they were once visited by many notorious pirates. Learn about exploring the Isles of Shoals.

Written by Dan Mathers
Dan is the editor of New England Boating & Fishing and the former associate editor for Offshore Magazine.
His freelance work has appeared in Backpacker, Adirondack Life, Cape Cod Life, South Shore Living, and many other publications.
Dan loves exploring the New England outdoors. He enjoys paddling, camping, hiking, and running ultramarathons.