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Tuscan Hill towns

Planning first trip to Italy with boyfriend in October- would like to spend 2 nights in countryside to get away from the city life. Any recommendations between Florence/Rome as well as suggestion for transportation? Some friends have suggested having a driver take us to hotel, and many hotels will provide driver for the day to see wineries. Please advice with any recommendations

Posted by
174 posts

I would suggest Siena as a home base or if you want to go smaller, you could look at Montepulciano or Pienza. All three are described well in the RS Italy book, which I suggest you buy if you do not have.

As for transportation, a train could easily take you to Siena. I’m not sure about the two smaller towns but I suspect you can only get there via car. I am sure a hotel would be able to set that up for you or you might ask for recommendations on here for local tour/wine guides.

We rented a car out of Florence and drove down to Siena and then used it to explore Tuscany. I don’t think the driving was really too bad, if you’re worried about that. RS has some nice drives. I believe there are a whole bunch of wine tours/busses that leave out of Montalcino as well.

Posted by
138 posts

We rented a car in Florence and drove to Certaldo, San Gimignano and Sienna through the back roads of Tuscany. Our GPS made it super easy. And then we took the Autostrade (interstate) back to Florence after dinner in Sienna. Very easy to do in a day. It was probably my favorite day in Italy.

Posted by
5 posts

We stayed in Pienza and loved it. The place we stayed was an agriturismo just outside of Pienza that we found on AirBnB. The wife would make wonderful breakfasts for us everyday. We also loved San Quirico d'Orcia. We rented a car in Orvieto (which is really worth a stop) on our way from Rome and drove through Tuscany. So many really cool small Tuscan towns in the Val d'Orcia. I felt like Siena was really crowed with tourists and more expensive.

Returning the car in Florence was a nightmare though! We should have taken it to the airport and found transportation to the train station in Florence. I was trying to read all of the Traffico Limitato signs so we wouldn't go somewhere we weren't supposed to but there was so much traffic and the drivers are not patient. We lucked out and didn't drive anywhere we weren't allowed to and finally found the rental return in town.

Posted by
16893 posts

Taxis or private drivers will be expensive for any significant distance. I'm not familiar with any hotels that will "provide" a driver; at least not for free. Several local tour companies operate out of cities like Siena. Some rural agriturismo properties may organize add-on excursion options of their own for a fee and would advertise that on their web sites.

Posted by
75 posts

Our local paper add an article about Villa Trasimeno a few years ago, and we plan to stay there next time we visit. For 330 euros per couple per day, it includes a room, transportation to/from airport or train station, sightseeing, breakfast and dinner.
http://www.villatrasimeno.com/