Day tours out of Florence

Jack - As one that has taken small groups throughout Italy I would say, honestly, rent a car. Hit the road out of Florence and in a day you can see Siena and San Gimignano, and even Volterra in the evening for dinner. A bit rushed but my gosh, you'll be on your own time and save a ton of money.
The rental companies will provide you with mapquest - pretty easy from Florence OR, you can take your GPS BUT - only if you purchase European maps.

Ciao, Greg

Having the car gives you great freedom to go from town to town at your own pace. Doing a few days in the country side like that in the Chianti region, and in all directions around Siena is awesome.

For instance last weekend I was in Greve for their annual wine event - and then took a road I had never been on before and ended up in Rignana, one of my favorite spots in all of Tuscany, for lunch. The scenery was so amazing I am still talking about it with my wife. Tomorrow we are going down to Panzano for a tasting event there and lunch at Mac Dario - and then maybe on to Siena in the afternoon.

Anyway - you get my drift probably. I am just not sure by the question if you are planning to take the car and stay out of Florence for those nights, or come back with it each day. Driving in and out of Florence can be a hassle, and parking can be a bit expensive too.

You can get some ideas for other towns to visit and wineries too here.

Maybe I should clarify . My friends are 6 persons and would need a van.If they spent 3-4 extra days in Florence and used 1 to bus to Siena for the day,then took a hilltown tour one or two days,it would eliminate the need to rent a van and still allow a feel for the hilltowns.