The first man to operate a ferry in Marblehead [Massachusetts] harbor was Philip B. Tucker, a direct descendant of the Samuel Tucker who won great fame as a naval commander during and after the Revolution. His ferry was a large catboat (an open, broad-beamed boat with a single mast and sail). When needed, he supplemented the catboat with dories in which people rowed themselves around the harbor. Tucker also operated a chandlery, delivering all sorts of supplies from coal to food to resupply the large yachts. He called his enterprise the Marblehead Transportation Company, and his base of operations was Captain William Blackler's Salt House. The road to the salt house was named Ferry Lane, and everyone referred to the ferry landing as Tucker's Wharf. Some of the greatest names in yachting history and at least one president (Grover Cleveland) landed at Tucker's Wharf.

A steam ferry named Escort, probably Tucker's, was wrecked on Marblehead Neck on June 8, 1882. It was replaced with two steam launches, and when Tucker died on October 15, 1900, other men were ready to take over the business.

Yachting boomed after World War II, the Transportation Company prospered, and a whole generation of Marbleheaders were introduced to the water in a new way, working on the docks, on the yachts and in the ferries servicing the harbor as well as fishing.

But in the 1970s, yachting began to change, and as the proprietors of the Marblehead Transportation Company aged, the company's fortunes began to fade. By 1992, the Transportation Company was bankrupt, its principal asset, a waterfront lot, had been irresponsibly contaminated with oil and gasoline.