I am coming from Rome. Spending 2 nighs in Siena and 3 more nights closer to Florence. I will want to do a day in Cinqueterre, a day in San Gimignano, at least a day in Florence. What is the best way to organize this. Travel to CT and San Gimi. from Florence or Siena?

From Siena to Pisa to cinqueterre.com

via La Spezia torrettas.com Manarola my fav

Regional Trains are cheap worked great for me

when there this May... back via www.Lucca.info

To Florence pick up San G 20 miles from Florence tour

best no train you can take a cheap bus though if budget

but tour worked best for me...

trinitalia.it

What time of year?
Will you have a car?
How many days total?

Siena and Florence are only 75 minutes apart and transport between them is easy so why split them unless you want easier access to CT, Pisa and Lucca?

SG is easily reached by bus from either Siena or Florence - you may need to change at Poggibonsi.

My wife and I made a similar trip 2 years ago, having already been to Rome and Florence on a previous vacation, our Itinerary for this trip was Cinque Terra then down into Tuscany. We made our sleeping arrangements at a B&B in Val d' Elsa, and made day trips to Siena, San Gimignano, Montepulciano and other hill towns I cannot spell. All of these drives were less than 2 hours and the drive was a pleasant part of the experience. My suggestion is find a central location and make day trips, not as much packing and unpacking. good lucj

1 day in CT is a long day if you are taking trains there and back from Florence. Consider if you really want to spend time there, and if so I would spend 2 nights there and 3 nights in Florence or Siena and day trip to the other, as well as San Gimi.