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risky or reasonable?

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Best place to stay in Napa is the EXPO--walking distance to town and restaurants and full hookup, not what you would expect at a county fairgrounds.  Expensive and need reservations long in advance, however. 

I also would be concerned about health insurance.  What if something happens and you become less healthy? 

Don't know your background other than your being an educator, but do you have any professional skills you can do online part time while you travel?  (I teach online, for example.) Volunteer and camp hosting jobs limit you to one area for several months and do not pay well.  Having a skill you can get paid for at a professional level would go a long way to paying for health care if your insurance gets more expensive.

However, I also say go for it.  Even if you have to spend more of that nest egg than you plan on, it is only money and life is short. 

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