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5 Days To See Tuscany Hilltop Towns In September

Probably not the first to ask this, but fresh answers are helpful.
Arriving & departing from Florence --- but main objective is to see & experience countryside Tuscany and hilltop towns as talked about in Rick Steves Italy guidebook and website.

We are allocating 5 days & nights for this (3 other nights in Florence) --- we would be grateful for advice from experienced Italy travelers who know Tuscany pretty good --- we intend to use the trains & busses to get to the hilltop towns --- we especially need advice for best use of time and geography, as in below questions:

  1. Would Siena be the best hilltop town to use as "base camp", returning there each night?
  2. Or -- is it feasable to see most of the hilltop towns as day trips from Florence?
  3. Is there a combination of 2 or 3 towns that make for a logical 1-day trip, returning to what base town in the evening?
  4. We don't mind changing base camps every 2 nights or so.

We don't mind a little bit of a fast pace, but not a hectic pace -- we just want to see all we can in a comfortable manner, returning to base each evening around 6 or 7 pm.

Thanks, everyone ....... Jim Parks / Lone Tree, CO

Posted by
10344 posts

A car is the most efficient way to see the hilltop towns of Tuscany.
Using public transportation is going to be challenging and take extra time.
This is one of the few times I'd encourage renting a car in Italy.

Posted by
15041 posts

Leave Florence nights for last.
Rent a car upon arrival.
Find a country hotel or villa or farmhouse outside of the cities. There are hundreds all over Tuscany.
The best base is somewhere between Florence and Siena, preferably near the freeway connecting the two cities. The area just north of Siena (Alta Val d'Elsa, or upper Elsa valley) would be ideal (Colle Val D'Elsa, Monteriggioni area). From there you have virtually all of Tuscany within 90 min drive.
Do not stay in the city center of Florence or Siena with a car as there are strict traffic restrictions.
After your five nights day tripping around, drive to Florence and return the car upon arrival. Return the car at either the airport or, if you use Hertz, the Sansovino location. Do not drive inside Florence city center.
Stay in Florence without the car for your last 3 nights. On the day you depart use a taxi to the airport (less than 15 min from anywhere in the city center).

Posted by
186 posts

Glad to read your response, Roberto. We are booked in early October at a sort of agriturismo in Noce (a couple miles north of Barberino Val d'Elsa) with a rental car (picked up in Florence at Hertz Sansovino) and plan to drop the car back in Florence, where we will stay a few days before continuing on with our holiday. I'll be interested to hear how Jim's trip goes, since there are some similarities.

Posted by
15041 posts

As mentioned above, visiting the Tuscan hill towns without a car is not ideal.
It is however possible. But it requires extra time since you need to deal with scheduled public transportation which is infrequent at some locations.
To do so I recommend to split your stay between Florence and Siena. Some towns are more easily visited from Siena, others are easier from Florence, which is Tuscany's capital and main transportation hub.
Since trains don't go on top of hills, often the best way to reach some towns is by bus.
Buses are particularly infrequent on weekends, particularly Sunday when there are very few runs. Therefore if you visit small towns by bus, do so Monday through Friday. Stay in Florence or Siena on weekends. If you travel on weekends go to places served by rail. Train service is just as frequent on weekends.

Posted by
7175 posts

If you are limiting yourself to public transport I would get the train to Siena (3nts) from Florence.
Do a day excursion to San Gimignano, Volterra by bus from Siena.
Then train to Lucca (2nts) with a day excursion to Pisa.

Posted by
11613 posts

I like being in cities in the evenings, so I would agree with staying in Firenze and Siena for a few nights each and daytrip from there. I love Montalcino, Pienza, Montepulciano, Arezzo, and Lucca.