This Scenic New England Cruise Hops Between Tiny Storybook Islands Off The Connecticut Coast

If you squint your eyes and tune out the American accents, you might mistake the Thimble Islands for somewhere in the Scandinavian fjords. Set along a stretch of national wildlife preserve along Connecticut's coastline, this archipelago is one of New England's most beautiful and underrated coastal escapes. While most tourists and summer-seekers rush towards the Hamptons, Montauk, and New Haven, the Thimble Islands are left to thrive as a tiny, uncrowded paradise of storybook islands in the Long Island Sound. And just like in the fjords, these islands are best explored on a boat cruise.

There are a couple of tourist boats that sail through the harbor between April and October. Two of the most popular group tours set sail aboard the Sea Mist and Island Time. The group tours, which are also available for private charters, spend just short of an hour trundling between the tiny islets, rocky outcrops, and larger islands in the archipelago. It may be short, but with a tour guide and reasonable ticket prices, it's a dreamy and affordable way to soak in the surroundings. 

The first time Europeans laid eyes on the islands was in 1614, but they were only settled around the 1750s. At this time, the islands were called the Hundred Islands, for obvious reasons. Over the centuries, the area has gathered its fair share of legends, the most iconic being the tale of Captain Kidd, a notorious pirate who supposedly buried his priceless treasure on the islands. With its natural beauty and rich history, by the 19th century, the Thimble Islands were already dotted with the yachts and holiday homes of wealthy New Yorkers –– the start of the elite tradition of New England summering. 

It might sound like a lot, but when we talk about 365 Thimble Islands, only around 180 of them have a name, and just 23 of them are big enough to support a building, dock, or a lighthouse. Speaking of which, there are no less than 23 lighthouses casting their unique light signals across the Long Island Sound, though only a handful of them are publicly accessible.

The Thimble Islands sit just off the coast of Branford, Connecticut, a charming town with water sports and coastal cottages. Scattered across them are some of the most prestigious holiday homes in the country, some of them on islands barely big enough to hold a single house. Most of the homes are historic Victorian-era cottages finished with fresh coats of white paint and delicate ironwork. During the summer, the area transforms into a buzzing vacation destination, with wake boats, kayakers, and swimmers scattered between islands, and sun-drenched seaside eateries catering to homeowners after a coveted lobster roll.

Most restaurants, bars, and breweries can be found on the mainland around Stony Creek and nearby in Branford. As for the islands, those that stay above the water at high tide are typically reserved for private residents, most of whom are seasonal visitors who vacate the chilly region in winter. Getting there is fairly simple: The Branford River inlet and harbor, the main departure point for exploring the islands, are just 5.4 miles or a 15-minute drive from the Tweed New Haven Airport, which connects to over 30 different countrywide destinations. If you're taking public transport, the scenic journey can take up to an hour and a half, passing through New Haven, a city that happens to be one of the best places to see cherry blossoms in the spring.

Thimble Island Cruises operates two vessels that tour the sound. The first, called the Sea Mist, travels around the Thimble Islands, while the second, named Island Time, navigates the Branford River and surrounding coastline. Unless otherwise noted, the Sea Mist departs from Stony Creek Dock, while Island Time, a 40-foot Catamaran design that can seat 28 passengers, operates out of Bruce & Johnson's Safe Harbor Marina, closer to the mouth of the Branford River.

The Sea Mist is a 44-foot, double-story Chesapeake-style boat with an open observation deck and heated interior, making it a great choice for families. Its narrated tours last 45 minutes. Tickets cost $18 per person, $12 for children, and infants ride for free. Come thirsty, as there is beer, wine, soda, and other drinks available to purchase on the cruise. The bar is cash-only, so make sure to bring along some change.

Beyond the regular sightseeing tours, the Sea Mist is also available for private events and charters. Whether you're hosting an intimate event or a casual celebration, you can book the entire boat for a two-hour or longer private outing. With this, you can either have the event catered with a well-stocked bar or bring your own food on board. A first mate will be available to help manage the bar and assist with logistics. The vessel can accommodate 38 passengers for private cruises, although for dinner cruises, they recommend keeping the group between 26 and 34 people for comfort. Depending on the weather, you can choose to explore the Thimble Islands and coastline towards Guilford, travel up the Branford River, or east to Sachems Head for a change of scenery. A 2-hour private charter costs $825, with an additional $25 for extra stops at docks or piers.