New England Traveler

Planning a New England day trip, weekend getaway, or longer adventure? Explore our curated New England travel directory, featuring picks from the editors of Yankee Magazine (the New England experts since 1935) for the best things to do in each state, plus where to shop, eat, and stay.

Thimble Islands Cruise

Best Island-View CruiseCaptain Bob Milne spins stories about Tom Thumb’s girlfriend and a tenacious mother-in-law as he steers his classic vessel around tiny islands crowned with modern and Victorian architecture.The Thimble Islands consist of some 25 tiny inhabited islands among a few dozen others scattered like spilled marbles off the coast near Stony Creek. These islands seem barely able to stay above the water, burdened as they are by the weight of local legend. (One of the Sea Mist Thimble Islands Cruise boats will take you close enough for a tantalizingglimpse.) Captain Kidd was said to have hidden buried treasure in the deep, narrow cove of Money Island in the dark of night. On Cut-in-Two Island sits the cottage where the 19th-century circus celebrity Tom Thumb courted the diminutive Emily. The home was wallpapered with circus posters; a century later, the poster collection was said to be worth more than the cottage itself.There’s an outlaw history to the area around the Thimble Islands, a windswept archipelago that’s home to an exclusive summer colony where an invite is required to step ashore. If none is forthcoming, no matter; hop aboard the Volsunga IV. As Captain Bob Milne pilots the boat past dozens of granite upheavals with names such as Money, Potato, and Mother-in-Law, he delivers a well-rehearsed spiel seasoned with stories about Tom Thumb and legends of Captain Kidd. Touristy? Absolutely. But we love it for what it is.

4 Indian Point Road
Stony Creek
Thimble Islands Cruise
Please Note: This information was accurate at the time of publication. When planning a trip, please confirm details by directly contacting any company or establishment you intend to visit.

Leave a Comment

Enter Your Log In Credentials