Tuscany - 2 1/2 days in the countryside - Help with an Itinerary


New member
I will be coming to Florence October 24. I've been to Florence and want to see the countryside. I will arrive on Thursday morning and plan on spending the day in the city. My plan is to rent a car and drive the Tuscan region. I want to see Cortona, Montepulciano and San Gimignano. I want to visit the little country towns - visit some wineries and anything else that anyone thinks we should explore. I planned on driving back to Florence on Sunday - we leave for home on Monday.

Can someone possibly map out an itinerary - recommend a medium priced hotel or B&B - restaurants and wineries. I'm not familiar with this part of the country. I speak italian fluently.

Any help will be much appreciated!


The Tuscan Expert ;-)
Staff member
Ciao BillD,

Do you need to go back to Florence on Sunday for your departure on Monday?

If you do, this is what I'd recommend:

Thursday - Florence

Friday - drive directly out on the A1 to Cortona.
I'd make anywhere around Sinalunga-Montepulciano as a good place to stay for the next two nights out. Depending on when you can check in, you can first spend the day visiting the hilltop towns in the area - in addition to Cortona, visit Castiglion Fiorentino and Lucignano.

Saturday - Visit Montepulciano, Pienza, San Quiricio Val d'Orcia, Montalcino (including the Sant'Antimo Abbey nearby).

Sunday - as you drive back toward Florence, stop in Monteriggioni a little past Siena, then continue on to San Gimignano. On the way to Florence, take road that takes you past Certaldo.

Saturday is the day you can visit wineries - you are in Montepulciano and Brunello territory. Aside from lots of enotecas in town, there are lots of wineries in the area - if you want to visit one in particular, you should look online for hours and such... otherwise just come along, stop at the Montepulciano tourism office early in the day and ask them to tell you which ones are open and do walk-ins. They'll know....

As far as accommodation, not knowing what your budget is, I'd recommend you start by looking on here: http://www.tuscanyaccommodation.com/montepulciano-accommodation/

If you don't need to return to Florence for departure, you could do the itinerary backward to work your way down...