Oaxaca is a great city, the evening life around the Centro is great. There is a hotel 1/2 block from the centro, good prices and lots of room to store your bike. San Cristobal de la Casa is another great place to visit, sometimes a little cool because it's up so high.
I'm interested in heading south this winter, will be trucking down from the east coast of Canada to where it's warmer (South Carolina?) and ride from there. What part of the east coast are you leaving from? I ride a klr650.
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