Hello all!
I am a new "Forodorite", and am enjoying reading all the great travel info supplied by so many! Love the driving itinerary from StuDudley. I am now suffering from information overload! My husband and I are traveling to Florence the last 2 weeks of May 2013. I thought I had our trip figured out, until I joined Fodor's Travel Forum! After reading all these excellent ideas and thoughts, perhaps we should modify our plans somewhat.
We had planned on 6 nights in Florence (taking a day trip to Lucca during that time), which would give us 4 full days for Florence. Then we drive down to Montalcino, staying for 2 nights. Should we visit Siena as we head down to Montalcino, or should we overnight in Siena? I read that Siena is super packed during the day, but that it should be experienced later in the day and in the evening..... aaarhg! Decisions! Should we stay in Montalcino longer? Is Pienze a better place to stay? We then drive up to San Gimignano for 2 nights; what exploring ideas are there from San Gimi? After San Gimi, we were planning 3 nights in the Cinque Terre (town of Rio Maggiore). Then home 
. If we cover all that we want in Florence after 3 days, we could obviously do another day trip from there (eg. Siena?)
Should we try to see Pisa?
We do not want to spend all our time in the car, charging around the Tuscan countryside trying to see it all; we also want some on-foot town exploring time. The Abbey in Sant'Antimo is a must-see on our list. Zoecat mentioned various towns further south of Pienza - they sound beautiful, but I am afraid that is too much. Just means we'll have to come back! StuDudley - would your friends consider renting out their house - we are neat, clean and do not smoke 
!
Any ideas and suggestions would be most appreciated! We're in good shape and like to hike and walk .
Mille grazie.......Mtlbabe
Traveling to Florence and Tuscany 2 weeks in May
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I wouldn't take any time away from Florence - it is a beautiful city with so much to see and do.
If you plan to stop in Pisa, that is easily done on the way to Cinque Terre. Consider dropping your car in Pisa and taking the train the rest of the way to Cinque Terre. You can't use a car there and will have to park it for your 3 days. Where are you leaving Italy from?
I definitely recommend a stop in Siena but wouldn't worry about being there in the evening.
If you were feeling energetic, you could walk to Sant'Antimo from Montalcino. There is a hiking route that passes between the two - I haven't personally walked it, but I believe it takes between 2.5 to 3.5 hours.
You are correct in thinking Siena can get packed during the day, and IMO is far more pleasant later in the evening. The same is also true fro San Gimignano where, during busy days, it might theoretically be possible to walk from the main gate to the main square by stepping on the heads of the throngs of tourists - such is the crush.
Opinions on Pisa are sharply divided among Fodorites. I am really fond of the place. I can understand why those who come for a fleeting visit,and see the tower and the surrounding masses of tacky souvenirs are put off, but there is far more to the city than just that. The area around the Duomo with the cathedral itself, baptistry and of course the tower are rightly a world heritage site. The interior of the Duomo is one of my favourites in Italy.
Pisa is definitely a place which benefits from an overnight stay - even more than Siena it changes completely once all the tourists and touts have gone home for the evening.
the lovely buildings of the campo dei miracoli are lit up, and they certainly look magical if not miraculous, and you'll have them almost to yourselves.
you can book your time to climb the tower here:
www.opspisa.it
personally, although i don't normally like one-night stands, Pisa, Siena, and san Gim are all places where they can pay dividends.
BTW, while you're in Florence, don't miss a trip up to Fiesole. a good way to plan your day if you're going to do this is to go to the monastery of San Marco [in the piazza of the same name at the top of via Cavour] then get the bus from the other side of the square up to Fiesole.
As well as lovely views over the city, you can walk up to the monastery of San Francisco, see the presepe and the weird museum in the basement full of the things the monks have brought back from their travels, including some egyptian mummies, then walk back down to the Basilica, the roman amphitheatre, and lunch!
Another "must" IMO is the rose garden in Florence - I gave directions on how to find it in this thread - and in May it is at its absolute peak:
http://www.fodors.com/community/europe/rose-lovers-hie-thee-to-florence-rose-gardens-open-15-may-to-30-june.cfm
Pienza is on the flat. It's much better as a base for daytrips, easy to drive into and out of. Whereas Montalcino is up on top of a hill.
I would hope places like Siena and San Gimignano are not quite so packed in the late May timeframe. We have stayed in both towns and really liked being there in the evening and morning before the crowds descended. Siena has a bit more to see.
Yes, Siena by bus or Pisa by train make good daytrips from Florence. You can also combine Pisa by train with a stop in Lucca in the morning.