WaterGirl

Five of us are spending five days in the Tuscany area - actually btwn Florence and Bologna. First time to that area for all of us -- first time in Italy for four of five. It will be grape stomping week, so I want at least some time at the vineyard, but also want to get a pretty good feel for that area. Cinque Terre is a *must see* day trip on my list, but other than that, have some *like to see* things, but not anything set in stone. Thinking maybe a day in Florence, a stop (brief) in Pisa to see the tower and move on, maybe San Gimigiano (spelling?) or Montepulciano area? What about Sienna?? Bologna proper??? We're planning to rent a car, which should make timing and access a little simpler, I hope...

HowardR

The information you have provided is a somewhat vague and general. A few questions:
Where are you flying into and out of?
Where are you staying?
Do those five days include your arrival and departure days?
What are you interests?
Just your general statements hint at more destinations than you can comfortably cover in five days:
1 day in Florence
1 day in Cinque Terre
At least part of one day in vineyards
Part of one day in Pisa
San Gimignano, Siena and Montepulciano can easily fill the other two days!
That fills up five days and doesn't even include Bologna.
You seem to want to crowd too much into what is a relatively short trip.

WaterGirl

Thanks, Howard. The five days do not include travel - we're coming in from three days in Rome and leaving on the 6th day for a one-nighter in Rome before heading back to the States. We are staying between Bologna and Florence in a guest house on a vineyard (owned by friends of cousins). The sights I posed were meant as more of a list of options rather than "must see attractions" -- The thing we want NOT to do is squeeze so much into so little time that we're (1) exhausted and (2) haven't really seen much of anything enough to enjoy and appreciate it. From our "home base," I do want to see the coast (stick my toes in the Med. Sea) and have heard that Cinque Terre is a good day trip and easy way to achieve that coastal goal, other than that, some time in the wine country south of Florence (maybe Banfi, Montepulciano, not sure??) and some time to enjoy Bologna for a day and the vineyard at which we'll be staying are priorities. I've heard Pisa is way over rated, but have heard that Florence is a 3-day minimum (aka - next trip to really enjoy), Sienna and Luca are amazing, San Gimingiano is fascinating, but alas, there are only so many days....Just seeking suggestions and advice for best ways to enjoy without over booking.

HowardR

Why not save Florence for another trip when you could spend more time there, and instead, spend that day in Tuscany. (One reason not to go to Florence is that it's hell driving in the city!)
So, I'd recommend three days of day trips in the Tuscany (and possibly Umbria) area, one day in Cinque Terre and one day in Bologna. Though not considered one of the "A list" cities in Italy, Bologna was a delightful experience and makes for a great day trip.
Now, your next step is to do a little research on the Tuscany area and draw up a list from which you'll create your three one-day itineraries. The first thing you'll discover is that three days is not enough time to see everything you want to see!

GAMBLE

If you are going in the summer months be prepare for crowds and heat. So you might get very tired trying to do too much in a short time. Florence, Pisa and Siena will be quite enough for the 5 days you have. Tuscany should be left for another time to enjoy with a car. Every town - S. Gimignano, Volterra, Val d'Elsa, Barberino, Certaldo, Castelfiorentino, Impruneta, Greve, Raddda in Chianti, Montevarchi etc. have their own Cathedral, town square unique in their own way and it takes time to explore and it is just beautiful. Get a good guide book and decide on what you want to do first.