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Tuscany day trips

My family and I will be staying at an agriturismo in the Chianti region (Villa Sant' Uberto) for 3-4 days in early September. We'd like to take some day trips but will have limited time and I know my kids would like to do some relaxing by the pool. If you had 2 days to "explore" what would be your ranking order between these- Florence, Siena, Orvieto (too far?) vineyards, San Giminagno...any others? We don't know what to make our priority. We've never been to Italy and aren't sure if we'll be back anytime in the next couple of decades.:(

P.S.- This is my first experience being part of a discussion board and joined both Fodors and RS. I don't want to be unkind, but everyone on RS is helpful, and nice and I feel very comfortable asking questions! Thanks so much you guys!

Posted by
196 posts

I spent 4 wonderful nights in Siena and highly recommend it. There is a beautiful Cathederal and the town square is beatiful. My wife and I were in the process of renting a car to go to San Giminagno from Siena when someone that was returning told us of the hoardes of tour buses and the mobs in the street. (This was in September too.) So right there on the spot we changed our plans. We asked the car rental agent (Hertz book before you go) of an alternate place, and he suggested a drive through Chianti. Best thing that happened on that trip. Visited wineries around the hilltop town of Rada. It was beautifu. One note on wine tasting in Italy. Make it clear the moment you walk through the door that your interested in buying wine. These small family run wineries are not interested in showing you the label of their wine like they do in Napa and pouring. Trust me. Just say, "I am interested in buying some wine, may I taste your's." The prices are VERY reasonable. Have a great trip!

Posted by
525 posts

Go to
I have found so many wonderful towns listed on this site that I would like to visit while I am in the Tuscany area for 6 days.
Way too many hilltowns to see but we'll do our best to see many.
We're skipping San Giminago just because of the comments we've been reading and we want to enjoy the smaller towns.
Happy Travel planning.

Posted by
6898 posts

Melissa, you have so many choices. Staying in or around Siena is just beautiful. We were at San Gimignano in 3 weeks ago and it is loaded with tour buses and people. There is really just one narrow main street from the Roman gate up to the church. It's very picturesque with the 14 towers and all but it is crowded. An alternate suggestion is Assisi. For us, it was stunning. Better shops and less crowded. A drive through the Tuscan wine country and hill towns is also relaxing and beautiful. Again, lots of choices.