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Seattle has a pretty good one. You can sail on both Puget Sound and Lake Washington. There are tons of marinas in the city proper as well as the suburbs. Lots of sailing clubs for beginners and those who don't want to own a boat also. Most sailboats can stay in the water over the winter too. The sailing season is much longer than in the Northeast. You can also sail all the way to Alaska via the Inside Passage. In terms of views I would say it's hard to beat, although Maine is nice too.
San Diego. Lots of safe harbor, excellent weather year round. Fishing is decent enough, although not like it is further north. Lots of excellent restaurants for when you are in port. Lifestyle is casual.
I’d be pretty interested in Cleveland, feel like those traditional old money types populated Cleveland. Which is a city that at least historically has tried to imitate East Coast culture.
Newport RI has the National Sailing Museum. I assume there is a reason for that, but it could be due to the past rather than the present.
Narraganssett Bay is pretty sheltered and the weather is gorgeous all summer, so I would expect some great sailing there. Of course, Chesapeake Bay is much larger, but which City would you to assign it as a "sailing city"?
I am going with Newport for now.
The SF-Oakland Bay is a large but it is cold and windy all summer.
Puget Sound makes Seattle a pretty great sailing town, but even in summer it can rain up till noon or so every day.
Florida would seem like it would have top cities for sailing, but I don't know much about Florida and sailing.
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