Honeymoon in Tuscany


New member

I've started planning our honeymoon in Tuscany in October and would appreciate your help :)

* We are arriving and leaving via Milan (Malpensa airport).
* We have 9 full days in Italy.
*We will rent a car.

We want to visit Florence and villages around Chianti area and Val D'Orcia area as well.
In addition, we want to stay one night in Venice at the end of the trip as I just can't resist it :). I have already traveled to Italy in the past and spent a week in northern Italy, but it's the first time in Italy for my fiancee.

The question is:
- We've found a nice accommodation in San Casciano In Val di Pesa (Chianti region). I read that Val d'Orcia region is very beautiful and want to visit it as well. Should we stay 7 nights in San Casciano In Val di Pesa and make one/two day trips to Val d'Orcia or to stay half of the time in San Casiano Val de pesa and half of the time in Pienza?
The problem is that we are coming from Milan and should come back to Milan (with one night in Venice before reaching Milan airport). It means that if we want to stay in South Tuscany (Pienza for example) in the beginning of the trip its about 5 hours driving from the airport.

Maybe you can advise what is the best way? Stay in one place with day trips to north and south of Tuscany or divide it and make the long driving from Milan airport to south Tuscany? Or maybe some other ideas?

Many thanks in advance for your answers!


Well-known member
Dear Alina,
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!


New member
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.


The Tuscan Expert ;-)
Staff member
Ciao Alina,

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 ;)