I recently returned from a 10 day trip to Italy and took a day trip to the Chianti wine country with the company Fun in Tuscany.
It was a fantastic experience and I highly recommend it. We went to two wineries, had an amazing lunch, had the best gelato in the country and spent time with a guide who knew the area so well. Our guide made the day so fun and felt like we had known him forever by the end of the day. https://funintuscany.com/
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