When Kaye Williams left his life as a commercial fisherman, he had no intention of leaving behind his passion for the sea. Instead, he and his wife, Vivian, began a new career sharing their love of maritime culture with others. With the help of family and friends, they spent 1982 transforming a weed-infested vacant lot into the family-friendly marina complex that would become Captain's Cove.

More than 350 vessels pass through in any given year, but you don't have to be in a boat or on a pirate's shoulder to join the summer celebration. Yankee magazine hailed Kaye and Vivian's creation as "quintessential summer fun at Black Rock Harbor," honoring the complex with an award for Best Boardwalk. Colonial and Victorian shops sell everything from old-fashioned candies and ice cream to vintage jewelry and nautical gifts for the dinghy in your life. A Queen Anne home originally built in 1893—and relocated to Captain's Cove a century later—serves as a museum, holding 18th-century navigational instruments, photographic histories of three local lighthouses, and other exhibits related to the legacies of Black Rock Harbor, Bridgeport Harbor, and Connecticut's oyster industry.

There's also plenty of space to sit back, watch the boats, and get your fill of fresh seafood. Overlooking the waters of Black Rock Harbor, the 400-seat restaurant is a sprawling complex of decks and gazebos where families share fried clams, lobster rolls, and fish and chips. No matter how nice the weather, you might still want to peek inside at the dining room's massive saltwater aquarium or view the hanging scale models of the Titanic and the flying boat Excalibur up in the bar. Even a night of karaoke or dancing to live music is suffused with history at Captain's Cove: the bar is built around the wheelhouse of a 19th-century tugboat.