In 1954, Tony DiMillo started his first restaurant in Portland, called Anthony’s, on Fore Street. They proudly claimed, “The clams you eat here today slept last night in Casco Bay.” In the 1960s, Tony moved Anthony’s to Center Street. Five years later, he opened “DiMillo’s on the Waterfront” just across the street.
In 1978, Tony bought the rundown Long Wharf from Canal Bank and turned it into “DiMillo’s Marina,” quickly filling all 120 slips. Then, in 1980, he bought an old car ferry for $80,000 with plans to turn it into a floating restaurant.
Originally called the “New York” in 1941, the ferry shuttled vehicles between New Castle, Delaware, and Pennsville, New Jersey. It later served as a ferry between Norfolk and Hampton in Virginia. In 1958, Rhode Island bought the ferry, renaming it the Newport, and it ran between Jamestown and Newport. But when Rhode Island built a bridge, the ferry wasn’t needed and was sold.
The city of Pawtucket got the ferry for $1 to turn it into a floating art space for young people on the Blackstone River. But the project didn’t last long. In 1977, the Setauket Yacht Club in Port Jefferson, New York, bought it and used it as a clubhouse and storage until the DiMillo family acquired it. On December 6th, 1982, DiMillo’s On the Water officially began serving customers, adding another noteworthy chapter to the boat’s extensive history.
