Philadelphia, PA

Dutch mapmaker Augustine Herrman first suggested building a canal across the top of the Delmarva Peninsula in the 17th century. By the 1760s, surveyors were scouting routes. Construction of the current canal began in 1824, and it opened in 1829. The route cuts 300 miles off the maritime route from Baltimore to Philadelphia. 

A stop in historic Chesapeake City means you've made it halfway through the 14-mile-long C&D Canal, which bisects the town. Ship watching on the third busiest canal in the world is the favored pastime; waterfront bars and restaurants along the promenade encourage this practice. Huge ships clear the 140-foot high Chesapeake City Bridge with awe-inspiring ease. The constant parade of ships and boats–from international cargo ships, working tugboats and barges, and fabulous mega-yachts to sailboats and classic tall ships–provides incredible photo-ops.

If you have bikes on board, another way to see the canal is via the 30-mile C&D Canal Bike Trail, which runs along the north side of the canal from Chesapeake City to Delaware City. The south side of the canal is home to the South Chesapeake City Historic District along George Street, a tiny jewel box of early 19th century Victorian homes built during canal construction.