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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!!!!

Posted by
290 posts

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!

Posted by
23 posts

+1 for Theresa’s suggestion; Anna gave us a really excellent tour of Siena in 2023.

Another suggestion, check Tours by Roberto. In 2023 he was picking up from either Siena or Florence. In our case, he picked us up in Florence (with our luggage), along with a small tour group, and at the end of the tour he dropped us at our next hotel in Siena. Check his website to see if any of his tours interest you.

Hope you have a great trip!

Posted by
17 posts

Sounds like a great plan—Siena + San Gimignano are perfect together, Pisa is easy by train on a separate day.

If you want to keep it relaxed, I’d skip big group tours. Something like this is more comfortable and flexible:
https://toursoftuscany.it/tours/siena-and-san-gimignano-tour/ . It would cost two of you a little bit more but totally worth it, considering private transportation.

It’s more of a private day with Siena + SG, guided walk, lunch stop, and no rushing around. Much easier than figuring out transport, especially traveling with your mom.