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Seeking Recommendations for Private Driver/Guide from Florence to Siena – November 20

Hi everyone,

I’ll be in Florence in November and am hoping to book a private day trip to Siena on November 20. I’d like to spend a few hours exploring Siena and maybe stop at a winery or small hill town along the way (like Monteriggioni or San Gimignano, if time allows).

I’ll be traveling solo, so I’m looking for a reliable private driver / guide—someone friendly, knowledgeable, and professional. I’d appreciate any personal recommendations or recent experiences, as well as approximate pricing if you have it.

Thank you in advance for your suggestions!

Posted by
6711 posts

RS recommends Tours by Roberto, who also appears in the RS videos. The cost for lunch and tasting are in addition to the tour costs. You can review the various options on Roberto's website. Enjoy!

Posted by
301 posts

We have used Silvia Capanni for transfers from Florence to Siena, but she also provides tours. She lives in Siena. You may contact her by email at [email protected]

Posted by
88 posts

I just came back from 10 days in Bolzano, Verona and Venice and used a company that did a wonderful job with driving us all around and in between towns including all of our transfer driving.
The contact here in the states is Nadia Schwartz, [email protected]
and her contact in Italy is See Italy Travel, [email protected]
They were both fantastic, very flexible when I made changes and completely on-top of everything with reminders and communication.
I mostly communicated with Nadia prior to the trip, and she was very nice and easy to contact through text, calling or email. Then when we were in Italy, I mostly texted with her Italian contact there. Super convenient and took a lot of stress out of the logistics part of travel, which I don't enjoy.
Highly recommend!

Posted by
3 posts

Thank you Allison for the recommendations. Did you used them as a private tour guide as well?

Posted by
88 posts

Yes, in Bolzano for a city tour and in Venice for a cicchetti tour, which was delicious and fun. They can arrange any kind of tour you want. We've been to Italy several times and have done lots of touring with a guide, but this time we mainly needed transportation services. Yes, I know the trains, busses and public transportation in general are very easy and accessible, but we were looking to make our lives easier without having to think about these things this time around. An indulgence that was worth every penny!

Posted by
987 posts

OOOOO Allison! That intrigues me so much :)

I'm also with fora and it is interesting to see how your experience with a travel advisor working with a Destination Management Company in the country works from the traveler's perspective!

Thomas, I think that you would need to go through an advisor (many advisors use them) to use the company, as many DMCs don't work directly with travelers. I think you don't need a company that specializes in doing all the logistics for a long trip, you just need a day guide/driver, which is probably what Pat and Charyl were suggesting.....

Posted by
1902 posts

I used Day Trip in Italy to travel from Rome to Orvieto, with stops at Sacro Bosco and Civita di Bagnoregio. I've used them elsewhere and always been pleased, but the one in Italy was especially nice, with a very comfortable vehicle and water and candies supplied.

https://daytrip.com/en/