Best/most picturesque Tuscan hilltown to stay at for 3-4 days plus must-see hilltowns in the region

How are you commuting, will you have a car?

We haven't decided & were thinking of taking a bus - would car be a better option?

"Tuscan region" is vague. Florence is in Tuscany.
Assuming you want to home base in the Tuscan countryside, you'll be glad to have the flexibility of a car.
There's limited bus service in the Tuscan country.
Just try to avoid driving the car into larger cities/towns, like Florence.

It is difficult to pick one place as a base for all places in Tuscany: it is vast. A car is, IMO, mandatory for touring the smaller towns and seeing the beautiful countryside.

If you like wine, Montalcino is great. It is a very cute town, quiet, good restaurants, parking is a 10 minute walk from the main piazza. You can drive between Montacino and Montepulciano stopping in Pienza for a nice day tip. Beautiful abbey at Sant'Antimo, another at Monte Oliveto Maggiore. You could even go as far as Cortona although that's a bit long of a day for me. Car mandatory.

You could stay in SIena and take a day tour of Chianti with Tours by Roberto, then rent a car for a day or two to see Volterra and San Gimignano, then Cortona and Arezzo. Zoe loves Arezzo, she may have advice about using that as a base....

Another option would be to do both. Our first trip here we spent three nights each in Siena and Montalcino, did the trip with Tours by Roberto our first day in Siena, then rented a care the next morning to take us through the rest of the time there, dropping it in Orvieto before continuing to Rome.

No hands-down winner, there are so many choices. Laurel's options are good. I've been to Arezzo several times but never used it as a base. It's got everything I like in a medieval city with a thriving modern city life.

I might prefer two bases in Tuscany, Siena for the southern part and somewhere near Firenze for the north, depending on how much time you have, to avoid driving longer distances when sampling wines along the way.

VibSri,
This may help http://www.slowtrav.com/italy/tuscany/hs_planning.htm

Thank you all for the info, so basically I have 4 days to see the following (I call it Tuscan region/hilltowns for lack of a simple way to collectively refer to all the Hiltons/imp cities in central Italy - Toscana region perhaps?): Sienna, Arezzo, Assisi, San Gimignano, Volterra, Montepulcciano, Pienza, Orvieto, Pisa & Lucca. Would that be possible? Plus, on the 5th day I need to get to Monterosso as early as I can.

We did a very similar trip - four days - and stayed in Pienza. It was perfect. Centrally located to all the towns you named. It is small, but we liked being able to park at the end of the day and walk to dinner, etc.

I just re-read your post. On our fifth day we drove from Pienza to La Spezia and took train to CT. I think drive was about 3.5 hours and train trip was very quick.

I would consider dropping your car in Pisa at the airport. Easy to find. There is a very short, bus ride into the main train station from the airport, there use to be a train, but the last time I was there they were rebuilding. From there you can walk or take a bus to the Leaning Tower of Pisa and then back to the train station and on to Monterosso. Parking is a problem at the tower. I personally wouldn't want to mess with a car. Of the cities you want to see, in my opinion, Pisa is the least inviting. I have not been to Arezzo, but the others several times each. I can't imagine doing Tuscany without a car. There are too many places in between the towns you plan to see to stop, even if just for a great photo.

I must agree with Laurel on two counts. Dropping a rental car in Orvieto and training in to Rome, if this is on your intinerary is a great option. I have done this two or three times. I have used Hertz, and there office is very small, but a short distance from the train station. The cathedral there is spectacular with its golden mosaic façade. I used Roberto also for a tour, at least 10 years ago, and it was very interesting. I also agree with the poster that mention Sant'Antimo monestary. We went in the evening just before sunset, and it was very peaceful and the monks were doing there vespers/chants. Not certain I have the right terms there. For me just driving in the beautiful undulated hills is reason enough to go to Tuscany. If I were in the area, I wouldn't miss Florence either.

For the places you want to see, you should rent a car. I traveled with friends for a week in Tuscany, using Siena as a base (we found a hotel at the city gate with adjacent garage parking). We went to two towns each day (most of the day in one town, shorter stop in the second).

Sienna, Arezzo, Assisi, San Gimignano, Volterra, Montepulcciano, Pienza, Orvieto, Pisa & Lucca. Would that be possible? Plus, on the 5th day I need to get to Monterosso as early as I can.

That's a lot in four days. I don't think you need ot hit every hill town to enjoy Tuscany, but If you have four FULL days and don't mind windshield time, I would say

• stay in Montepulciano, day trip to Pienza and Montalcino one day

• another day spend in Siena and have a look at Monteriggioni a unique walled town near Siena

• a third day go to Orvieto

• fourth day Arezzo and Cortona OR San Gimignano and Volterra

• 5th day if you have time on the way to Monterosso, stop in Pisa and/or Lucca

We have learned that a GPS will save a lot of time and frustration in Tuscany. Bring one along!

EDIT: Drop your car in La Spezia on the way to Monterosso.

A car is a definite for the Hill Towns - and a GPS is much-needed. Even with a GPS from the rental car company, I don't think we ever returned to our B&B over the same roads! We stayed in the Laterina area outside Arezzo. If you're going to Florence or another city, the train is the way to go. Arezzo has a great train station and easy parking. I'd think about that for a Tuscan home base. Easy access to Florence, Siena, San G, etc. Deruta is a lovely side trip if you're into Italian pottery - wonderful souvenirs!

If, because of distance, you lop off Pisa, Lucca and Orvieto, and base yourself somewhere in Chianti.
1 Montepulciano, Pienza, Montalcino
2 Siena, Monteriggioni
3 Arezzo, Cortona
4 San Gimignano, Volterra

Thank you!! Lots of valuble info and i'm taking notes. And yes, definitely plan on renting a car as well. Also, we intend staying in Florence for 2 nights - too much? I figured just the Uffizi would demand a good part of the day...

Yes you need minimum 2 nights in Florence to give you a full day ...
Accademy - Duomo - Piazza della Signoria - Uffizi - Ponte Vecchio - Piazzale Michelangelo
You could easily fill a 2nd (or 3rd) day - Medici Chapels - Santa Croce - Palazzo Vecchio - Bargello - Pitti Palace - Boboli Gardens

With kids in August and a car I wouldn't stay in a hill town. I would choose an agritourismo with air conditioning and a pool. Day trip to monteriggione or montepulciano for examples of the kind of towns you describe. Dropping the car in Orvieto before taking a train to Rome. Overnight in Orvieto which is a very easy town to visit.
There are so many great hill towns you won't get much agreement on which to visit.

Good idea but as I understand it, agriturismo requires a minimum stay of atleast a week or so? And after revising itinerary to include days in Florence, i found we don't have enough days to seek such accommodation...

Thanks also, djp_syd - we have 2 days in Florence, only, one of them happens to be a Monday and on the other day we have to cram the museums plus the Vasari Corridor & Boboli gardens!

And on another note, how do you insert an image in this forum if you need to?

Regarding Agriturismos and minimum stays, we are staying at Agriturismo La Crociona (near Montalcino) this July for three nights.

Having journeyed throughout Tuscany a few times, I've gained new insights for future travels. I've used the Hertz in Orvieto...great option and convenient. Stayed at an Agritrurismo just out of Orvieto with a view of the city too....wonderful.

There is a Hertz in Chiusi just across and up the street a bit from the train station. Then from there one could drive to anywhere in the region. Montepulciano is just a short drive north of here, and Pienza to the west, etc.

In Camucia (Cortonas train station town) there is SIXT car rental (http://www.sixt.it/auto-noleggio-cortona-arezzo) and I am using them in September so I can spend some time over in Montepulciano and the Val d'Orcia after my stay in Cortona. Get super cover to get deductible to zero. The only thing is, you have to walk a few blocks from the train station. I've done the walk and it wasn't bad. A great bar/caffe on the way too, and a laundromat next door to it. But they might meet you with car at the train station. When I was going to use them last Spring in Cortona, they were offering to drop the car at Piazza Garibaldi in Cortona, so might ask them.

A short drive north of Pienza, and south of Montisi is Sant Ann in Caprena (http://www.camprena.it/) where English Patient was filmed. You can stay here for 90euro night, dinners 20 euro with wine per person last I checked. I'm very interested in staying here sometime.

The charming town of Montisi a short drive to the north is a relaxing study in history and how Tuscan towns were built so as to defend themselves. There are nice places to stay in Montisi too, so that's an option that answers your original question as well. It is NON TOURISTY.

If you stay in Pienza, Montepulciano, you're closer to much of the sites and towns, and shops and eateries are a short walk from your hotel or B&B. I love Cortona and it's across the Val di Chiana but a must see, and good for achilles tendon stretches. wow, is it ever.

Terrapille Agriturismo is just situated a short distance south of Pienza on the road used for scenes filmed for the movie "Gladiator". I walked and photographed the road and area last Spring and it is beautiful. I didn't stay at Terrapille but I know Rick Steves has as indicated in one of his programs.

This year I'm staying at a B&B we love in Cortona, and then at a B&B right in the center of Montepulciano. While there, I plan to drive into strada gladiator, pienza for more photography and the sweet life. Then a B&B we've stayed before in the Oltrarno in Firenze on my way home. So many amazing options in Tuscany alone. No time to try them all.

Last year we spent a week in Firenze, and then a week in Cortona. What we ended up doing was day trips via bus or train to various places like Lucca, Siena, Orvieto, Montisi, Crete, Val d'Orcia, Pienza, Montepulciano (friend from Siena with car took us to some of these). We used Tours by Roberto to go to Montalcino, Lucignano d'Asso, etc.

I would avoid long drives between points if you can since it takes so much time, and vacation time is precious. When we toured with Roberto, he had to drive from Siena to Firenze and then back past Siena to go where we planned. It uses a lot of time, so if you can locate yourselves near much of what you want to see it's makes better use of your time. I found that instructive if I ever planned a trip like the one you're proposing.

Lucca is out there and I'm glad we finally visited. We had a friend there so she gave us the grand tour and we spent the entire day. It was a nice train ride from Firenze, but we were staying in Firenze.

It's funny now to realize....I never rented a car or drove this last trip as it just worked out I didn't need to. When I stayed in Orvieto in 2012, I drove out to Bagnoregio and visited Civita di Bagnoregio too. Great day.