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Best place to live given these priorities?

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Hi, my husband will be retiring from the military soon and we finally have a chance to choose where we would like to live. I can work anywhere in the U.S. since I work from home or travel. My husband can work almost anywhere--he is in medicine.

We would really love to have some input of places you've lived or traveled in the U.S. that may fit our needs/wants. While together, we have lived in San Diego, a Fort Lauderdale suburb, Chesapeake Virginia, and New Bern NC. Separately, we have lived in Annapolis, South Shore Boston, Western Massachusetts, Reno Nevada, and SE Texas.

We are looking for the following:
--A great high school for the kids
--Close to the water. We have a large boat--and could even live on it (again) if the location were right.
--A smaller town feel where we could walk or bike-ride to shops and restaurants
--Fairly liberal attitudes--not a staunchly religious community
--Outdoor sports, such as biking, hiking, etc.
--Wineries nearby would be nice but not a requirement
--Light traffic (if possible)

We are thinking somewhere in Oregon or Maryland but we would love to hear your opinions! Thank you very much...

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