I have found some reasonably priced tours departing from Siena to Montepulciano and Pienza , Chianti and San Gimignano through Viator. They take max 8 people and it is about 8 hours. On the other hand there is the option of getting a private driver with the flexibility to return whenever I want. I like the fact of being with other people, having lunch with them on the tour but I am not sure if 8 hours is gonna be tiring and if it may even take longer. If budget was not a concern which one would you vote for? Thanks a lot in advance

I've done some small group tours such as you're describing. I've never been stuck with unpleasant people, but that's always a possibility. Of course, you probably have the option when you get to a stop of wandering on your own and meeting the van at the scheduled departure time.

I'm a solo traveler, so sometimes I enjoy the camaraderie of joining other travelers on a tour like this. But I've also done private tours, and you can have that same (or better) experience by getting to know your local guide. Consider that you're traveling all the way to Italy not to spend the day hanging out with other American tourists. It might be more enlightening, educational, and personal to spend your day with a local guide.

If money were not an issue, I think maybe 8 times out of 10 I'd go with the private guide. For me, money is an issue, so I probably do the group tour 8 times out of 10. Or I just do it by myself.

By the way, I once hired a private guide for a day trip, and I was prepared to pay him a lot of money for a customized trip. The day before, he told me he had a group of Americans who were joining us, and then he gave them a trip customized to their interests, and I ended up feeling like I was tagging along. They were nice people, but I was very angry about it. It would have been worth the extra money to get the tour I asked for. So be careful that you don't get into a situation like that. If you hire a private guide, make sure he or she gives you the experience you want.

It always is for me, but if money were no object, I would probably take the private tour to have more interaction with the local guide.

Thank you very much!

I like the idea of learning from the local guide. I am traveling solo too but I agree that I don't want to spend my time with Americans this time.

Ico1984 is back, advertising his tours.