My family and I are planning a trip to Tuscany in May or June 2018. We're thinking of flying into Florence and making it the base for the majority of our trip, since we don't want to drive much. From there we're thinking maybe 6-7 days in Florence to see things there, as well as taking day trips into the surrounding towns (Siena, Piza, Lucca, Arezzo, etc). Then we thought maybe 3-4 days in the Tuscan countryside to see the Val D'orcia region, where we would rent a car. I saw some nice places in Montalcino to stay in. That leaves a few days to do other things, which I guess we could also add a few days either to Florence or the Val D'orcia stay. Does this sound reasonable? Any recommendations? Thank you.
We found it easy to fly into Pisa Airport as it's much larger than Florence. Then we took a 1 hour train over to Florence.
Florence can be seen in about 4 days. We rented a car and drove about 1/2 hour south to stay 4 days in an agriturismo. We visited Siena, Volterra, San Gimignano and Certaldo on day trips. There are also a number of other hilltowns that are available.
We turned our rental car in at Orvieto and spent a day and night there. It's a very popular hilltown. We took the train into Rome--70 minute ride to Rome Termini.
I really like Florence, but the last time I was there was mid-May 2014 and the city was jammed with tourists. Do go there and spend all the time you need to enjoy the sights, but then move on to somewhere else as your base. . . maybe Siena?
Also consider Umbria - just as lovely as Tuscany.
Airports - look at Bologna too or even Milan.
I'm from NYC so I'm not bothered by tourists and a lot of people. Nothing can be worse than Manhattan, haha. I was thinking of Florence as a base for the majority of the trip since I know the transportation would be very easy from there and we don't really want to drive (except in the Tuscan countryside).