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On the northern tip of Door County on the Peninsula in Wisconsin, in Lake Michigan, is Washington Island. One has to ferry to the island. There is a great and continuous history of fishing up here.   While beautiful now, quite cold and harsh come winter.  

I  While it was below 0 F temps in Chicago, I was in the Florida Keys enjoying the balmy weather.  Spent a couple days on the beach and looking at art in Key West, FL. Roosters crowing are one of the fun sounds as the wild roosters are a common site. Lots of historic buildings.  Definitely a sense of being at the end of the line and an adventurous feeling.  Lots of pirate stories and colorful people.  To me, the real adventures are here and not at Disneyland.  But... maybe don't keep the kids out after dinner :D. Historic home on Key West, FL

Stayed a few days in South Beach, Miami and went to a museum that told about the saving of the historic hotels along South Beach.   A man and woman saved them by getting awareness and taking it to the government to protect the historic hotels.   I really love the neighborhood and the colorful Art Deco buildings.