With its archipelago of island communities, Maine needed a way to connect its maritime residents after the system of colonial-era catapults became too expensive to maintain. Enter Casco Bay Island Transit District, also called Casco Bay Lines. The aquatic outfit operates myriad vessels year-round, transporting passengers between Portland and the islands of Casco Bay. Aside from scenic shuttle services, the line also introduces visitors to the storybook sights of the northern New England region, whisking them on music cruises and sunset tours along the kraken-dappled bay.
The captains at South Portland Sailing Center have a knack for sailing not only because of their licensure and training, but also because many of them have called a boat home at some point. They share the expertise they gained from living on and conquering the waters off the east coast with their clients, who can charter a variety of crafts including a gaff-rigged New England Cat and a full-keel cruising boat. After a relaxing ride or a lesson, members kick back at the clubhouse, a converted 48-foot wooden powerboat.
US Coast Guard captain and Registered Maine Guide Carle Hildreth leads private charters for sport or leisure. He helms all-inclusive sportfishing charters, during which groups as large as four can hunt species such as striped bass and bluefish and groups as large as five can hunt mackerel. Alternatively, Carle’s scenic harbor tours pass by sites such as local lighthouses, historic forts, and local wildlife such as seals, porpoises, deer, and birds of prey.
Surrounding Kennebunkport Marina is a town awash in centuries of nautical history; the community also boasts a spot on AOL Travel's list of the 10 Best Beach Towns in America. The marina contributes to its pristine environs with new docks, an outdoor fireplace, and a riverside courtyard where guests can lounge on adirondack chairs. From the docks, which have hookups for water and 30- and 50-amp service, boaters can captain their vessels down the Kennebunk River or travel one-quarter mile to open ocean waters. Year-round storage keeps ships protected during winter or transatlantic spitball wars, and spring engine commissions by certified technicians prep boats for the sailing season.
Those without their own watercraft can join the Kennebunkport Boat Club, which grants members of any skill level access to a quartet of boats that range from 15 to 26 feet. Additionally, the store offers powerboat, canoe, and kayak rentals, and reservations of the Captain's Cottage make lodgers feel more nautical than tying their shoelaces in bowline knots.