When I was talking about fun cities, I should have mentioned those little towns in Alaska. You can fall in love with any of them. Some are so small you can cover every inch of every street in an afternoon. The weather in September is great. I've been twice, both times in September, so I can't vouch for the weather in other months. I'm sure there are times when weather is a problem.

Weather is seldom a problem in Hawaii, where there are some really great small towns and one really great city. I like Poipu Beach on Kauai and Lahaina town on Maui. Kalaupapa town on Molokai is Hawaii 1920. Don't look for the Wal-mart there.
Hilo, on Hawaii, is an old historic seaport. It rains a lot, but usually it's just a quick mist. You will love the people.
Howard