Have there been instances of ships or boats being capsized or badly damaged by tornadoes (waterspouts)?
Yes. Watercraft are especially dangerous in tornadoes because of the open and unprotected exposure, difficulty of reaching safe shelter and direct risk of drowning. On 1 Jul 1814, a tornado moved off land into Charleston SC harbor, hitting the anchored schooner Alligator. The “Gator” sank and killed 25 of 40 crew. This is the deadliest marine-tornado event in U.S. records. On 17 Jun 1978, the tour boat Whippoorwill, on Pomona Lake KS, was capsized by a tornado, killing 16. NOTE: Historical tornado information used here comes from both the SPC database and Grazulis (1993).