Canandaigua sits at the northern end of Canandaigua Lake, one of the broad, clear Finger Lakes south of Rochester. It is more workaday than storybook Skaneateles, but that is part of its appeal: a real small city with a long main street, boat traffic at the pier, and lake hills rising just beyond town.
The best reason to stop is the mix of water and old Finger Lakes prosperity. Canandaigua City Pier still feels tied to the lake's steamboat past, Sonnenberg Gardens gives the city a grand Victorian estate, and Granger Homestead keeps a quieter Federal-era story alive.
Canandaigua works well as a relaxed Finger Lakes base. You can spend a morning in the gardens, walk the pier at sunset, catch a summer concert at CMAC, and still be within easy reach of wineries, Bristol Mountain, and the smaller lake towns to the east.