May 13, 2014, 04:15 PM
San Casciano-Pienza is about an hour and a half driving distance, I think it's an affordable day trip for visiting southern Tuscany.
Southern localities, Castiglione d'Orcia for example, are located at less than two hours drive. You could arrange day trips also (Castiglione is situated in the Val d'Orcia, a must if you visit southern Tuscany: marvellous landscapes and deliciuos food and wine, if you've ever seen a Tuscan postcard, it was surely a representation of Val d'Orcia!) to this area or arrange instead a two-three days trip to southern Tuscany (Val d'Orcia, Monte Amiata, Chianciano Terme with its natural spa, Montalcino and Montepulciano for tasting the prestigious red wines). Then you could turn back to San Casciano and rest one-two days before leaving to Milan.
To me these options are better than choosing the long driving to or from Milan airport: you're on a vacation, you should just relax and enjoy your time here!
May 14, 2014, 06:38 AM
Ahhhh... A honeymoon in Tuscany. How idyllic. My husband and I did the same, 4.5 years ago. I can definitely recommend Castello Vicchiomaggio, which is a few km north of the town of Greve in Chianti, and about half an hour's drive south of Florence.
May 26, 2014, 05:27 PM
Congrats on the upcoming wedding!
Since you're coming in October which is already mid-season, I'd recommend breaking up the 7 days in 2.... spend the first 4 days in San Casciano and the remaining 3 in Pienza to visit the Val d'Orcia.
That way you're closer to all of the sights in each area, spending more time at each rather than in the car.
From San Casciano, you can visit Florence, Chianti, Pisa and Lucca (both on one day) and San Gimignano and Volterra (one day for both).
From Pienza, you can visit Siena on one day and then spend the other 2 days in Val d'Orcia between Pienza, Montalcino, San Quirico and Montepulciano, as well as Bagno Vignoni
June 7, 2014, 09:41 AM
Thank you all for your great advice!