We will have an extra day to either explore more of the town or do some wine tasting nearby. Can also vouch for doing a cooking class, but from the little bit I have searched they tend to be expensive. Looking for ideas of how to spend our free day. We will have a car and this will be for early June. Perhaps a nearby farm showcasing cheese making or a really good winery with good food nearby. Looking for your highlights :-).
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How about wine tasting 1/2 day tour of San Gimignano? You can drive because of the car. Otherwise, there are day time tour buses from Siena to San G. that simply charge a per person fee and include wine. You can book these easily in Siena with a hotel front desk clerk or tourist station.