The map is inaccurate but the itinerary is getting together.
Boone, NC
Chattanooga, TN
Birmingham, AL
Thibodaux, LA
Houston, TX
San Antonio, TX
Sailing near Austin?
Albuquerque, NM
Grand Canyon, AZ
San Diego, CA
Watsonville, CA
San Francisco, CA
Napa, CA
Napa, CA
Portland, OR
Salt Lake City, UT
Denver, CO
Eagle Butte, SD
Kirksville, MO
St Louis, MO
Muskego, WI
Chicago, IL
Suggestions, invitations, warnings, and other thoughts are welcome in the comments!