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5 nights-4 days in Spanish Basque Country-Advice needed

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We will arrive in Bilbao at 9:30pm on a Sunday night (May 2012). We will have 4 full days (M-Th), plus Friday to drive (or take a bus) to Santander to fly out to Seville at 3pm. We would like to spend time in San Sebastian, as well as do some wine touring in the Haro/Laguardia area. I would like to at least spend one day wine touring, and then stay somewhere overnight in a small quaint town or countryside for the night, (if not two days/nights). Any ideas on how to best route this? A rental car is an option, but so is public transportation. Also, should we plan to stay overnight in Bilbao on our first night and head out to one of the locations in the morning, or should we just continue on that night by train, if that is even possible? Want to avoid any unnecessary hotel changes if possible. And if so, which location might be better to start with considering we will need to get ourselves to Santander at the end of our trip. Really confused about location logistics...and could use some advice.

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