Discover Thimble Islands in Connecticut

Cruising the Thimble Islands, an archipelago consisting of small islands located in the Long Island Sound (about an hour south of Hartford, Connecticut), is a great way to discover the charm of New England. This was a great activity for a multi-generational trip including grandparents and our toddler. We were all able to enjoy the outdoors without it being physically demanding.

Cruise Logistics

The cruise boats leave from the harbor of Stony Creek, a small New England town by the water. Street parking can be found around the harbor which is conveniently located minutes from I-95.

There are two tour companies operating tours. Sea Mist with Captain Mike (operating every 2 hours) and Volsunga with Captain Bob (operating every hour) from late morning to early evening.

It is best to check ahead of time and make a reservation to ensure there is no change to the regular schedule due to private excursions.

We boarded the Sea Mist after a prolonged wait due to our target tour being reserved for a wedding party. Though it was a little frustrating at first, the weather was beautiful everyone pitched in with entertaining our toddler as we wanted in line.

Hats off to Captain Mike who made a special trip in between the scheduled times to accommodate the line of visitors who were not aware of the wedding reservation.

The tours last for about 45 minutes.

What to Expect from a Trip to the Thimble Islands

The view of the islands from the boat were spectacular. Most islands consisted of beautiful construction and impressive vegetation on what seemed like very rocky terrains. Each island is named and some are large enough to have several houses built. Bear island functions as a granite quarry supplying export quality stones. Several islands are maintained as ecological laboratories or wildlife sanctuaries.

 We enjoyed Captain Mike’s narration of the history and background about each island. Having visited the thousand islands a few months ago which consists of a much larger collection of islands, this tour felt like a condensed version.

Though it is recommended for children 3 years and up, toddlers and babies are allowed at no charge. If little ones are being held at all times, we didn’t feel there was any danger to them being on the tour. Our little one enjoyed the fresh air as he took in his new surroundings with excitement

 

Where to Eat in the Thimble Islands

There a few options for a post tour snack. We stopped by The Thimbleberry, the namesake cafe of the islands, named after the Thimble berry, a relative of the black raspberry family, for some delicious ice cream.

If you’re looking to do lunch or dinner, I would recommend looking checking out a few neighboring towns which has more dining options. We had a great sit down meal at The Wharf restaurant at Madison Beach Hotel, a few minute drive from the Islands.

A trip to Thimble Islands will surely make a great day trip to families from Western Massachusetts, Hudson Valley or NYC. It can also be a good stopover if you’re on a road trip through Connecticut. It was a relaxing activity that treated us to scenic views and fascinating stories about its residents.