It depends
If you are experienced and reasonable, you certainly could sail a 19 ft boat in the Bay Area, but you would have to be careful, avoid the slot on July afternoons, and head in when it starts getting really rough. The plus side: there is always some part of the Bay where you would be sailing happily along.It might be worth noting that the smallest keel boat most sailing clubs start students in is about 23 ft.And then when you look around, you'll see lots of sailboards and high performance small craft. The captains all seem young, happy and wet.If you want to stay dry, bigger is better as it would be a challenge. Good luck,S.