Driving routes and must sees


New member
Hi all. Travelling to Tuscany on 7th September and plan to spend 6nights there.

We fly to Rome and will make a beeline to Cortona in the rental car. Our plan then is

2nights in a rural farmhouse in Cortona

2nights in the centre of Pienza

2nights in a charming hotel in Orvietto

The Orvietto part is part to break up the journey from Tuscany to Amalfi where we will be spending a few more nights.

As this is our first time I am hoping for some tips on drawcard driving routes and tick off the box activity during our 6night stay. Might I also add we haven't paid for any accommodation as yet and thus any input on whether this is a decent itinery of locations to hang our hat would be much appreciated.



The Tuscan Expert ;-)
Staff member
Ciao firsttimetuscar!

Glad you asked because I'm wondering whether you are planning to make it to Florence at all? If so, I'd suggest changing the two nights in Pienza to somewhere further north so you're driving is less.... both Cortona and Pienza are in southern Tuscany, great if you're planning on staying and exploring just that area without too much driving on any of the days.

So here are my suggestions:

2 nights in Cortona - use these days to visit Cortona and Arezzo one day, then the other day Montepulciano, Pienza and Montalcino (quick stops near San Quirico for picture taking).

Then instead of staying in Pienza, head north toward Chianti.
For 2 nights, how about staying at Palazzo Malaspina or Villa il Poggiale or Casolare di Libbiano?

Your third day, on the drive up from Cortona, you can stop and visit Siena. Arrive at your destination for the night, but if you have time in the evening, drive out to San Gimignano for dinner (if you have time). The next day visit Florence.

Then you're heading back down to Orvieto - before driving down, you can stop in San Gimignano if you didn't see it before two nights before.... then drive down.

Ok that's it - I think that will be better place to stay than Pienza to see a little more of Tuscany, including Florence!


New member
Thanks a lot for that Lourdes. Actually we are purposely not doing north Tuscany. As we only have 6days we have decided to do Florence etc maybe next year. Just don't want to cram too much in.



The Tuscan Expert ;-)
Staff member
OK that certainly changes everything! ;-) I wholeheartedly agree with the plan to come back and see Florence and other sights closer to Florence on another trip :).

In that case, I'd do the 2 nights in Cortona to see Cortona itself, Arezzo and maybe Montepulciano. There is also a small village called Sarteano in the area - an article on what to see there will be up on the main site shortly, I'll link to it below as soon as I can.

Then on the other two nights in Pienza, I'd see (aside from Pienza of course), San Quirico d'Orcia, Montalcino (and the Abbey of Sant'Antimo) on one day, and on the other: Siena! :)