The GOODTIME CRUISE SHIPS began their river and lakefront tours in the late 1950s after Herb and Vince Fryan bought a 62-by-16-foot boat with a capacity of 68 people in 1957. The brothers, who had been involved in projecting and distributing movies, decided they could make extra money in the summer by giving river tours. They helped finance the purchase of the Goodtime by selling a small 22-foot homemade boat that Herb Fryan built in his garage. The name Goodtime was chosen to commemorate the original Goodtime Boat, which was operated by the Cleveland and Buffalo Transit Company (C&B Line) from 1924-1938 and ferried passengers from Cleveland to Cedar Point and back. The ship, originally the City of Detroit II, was built in 1889 and made 1,215 round trips and 1,220 moonlit cruises before ceasing operations in 1938. It was scrapped in 1941. The Fryan's touring enterprises were launched in 1958 and became so popular that in 1962 the Fryans bought a second, larger vessel (100-by-31-foot), which could accommodate 475 guests. They dubbed it the Goodtime II and eventually sold the Goodtime in 1965. The cruises up and down the Cuyahoga River and through the Lake Erie harbor offered lessons in the history and development of Cleveland. During evenings throughout the summer, they also took the boat out for dances and dinner parties. Herb Fryan ran the ships, while Vince Fryan handled the business end of the operation. In the early 1980s a ship christened the Goodtime I, in honor of its predecessor, was purchased. The ship, originally purchased to conduct cruises to Cedar Point, was a disappointment because of its slow speed. In 1984 the brothers sold the business to Vince Fryan's son, Jim, and took the Goodtime I to the Lake Erie islands to start a new sightseeing tour.

The business, based at the East 9th Street Pier, continued to grow under Jim Fryan's direction with the revival of Cleveland's lakefront. In 1988 Fryan made the decision to build a new ship. The Goodtime III, 151-by-40-foot with a capacity for 1,000 passengers, was delivered from a Louisiana shipyard in 1990. The following season, the passenger attendance surpassed the previous seasonal record by 45%. Bruce Hudec, who started as a deckhand in 1971, captained the ship throughout the 1990s.

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