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Day trip small group tours from Florence

Hello y’all!

My mother (70) and I (31) will be visiting Florence during the first week of November. We have 4 full days in the city, plus an additional day where we have the option of either leaving for Rome early or late in the day (we are starting out our trip in Rome and returning for the last evening for a direct flight back to Dallas).

All that being said, we would like to take day trips to some combination of Siena, San Gimignano, and Pisa (not necessarily all on the same day!). We have decided on these places despite some folks saying to skip them, etc, although we are open to suggestions (I’ve wanted to see SG since I was a kid and we both want to see the Leaning Tower, despite it maybe not being too exciting).

Does anyone have any recommendations for small group tours that might cover some combination of these? We are very used to touring on our own, having used trains and rental cars for trips across Europe before, but would maybe like to just be able to relax a bit more. I would like to possibly visit a winery for the experience, but neither of us really drink, so a wine tour wouldn’t be up our alley. We would preferably like to keep the budget below $500 for both of us combined if possible and would definitely rather small or private group as opposed to a coach trip. We are also open to just going by ourselves to one of these and combining the other two on a tour.

Thank you!!!!

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I highly recommend arranging a private tour of Siena with the fantastic Anna Piperato sienaitalytours.com if you can. You'd take the 131R bus from the Florence AT terminal on Via Santa Caterina da Siena for the just under 1.5 hour 1-way trip. Anna is a licensed guide with a PhD in Art History and is truly exceptional in her guiding expertise. An American ex-pat, she's lived in Siena since 2014 and is a professor and the English voice of the Palio of Siena. Two thumbs up to infinity and beyond. Enjoy your trip!