<< Will driving in general be an issue in Southern Tuscany? >>

Extremely easy driving. Very little traffic except near cities.

<< Is it easy to pull the car off to the side at any time and stop to take pictures? >>

NO. The roads are narrow and winding. You have to be very careful about pulling over and parking - need to make sure that any cars approaching from either direction can see your car.

I don't consider Siena as southern Tuscany - it's more in the middle. I stayed in Pienze and loved it - a small town in a beautiful area.

Take a look at this thread.

http://www.fodors.com/community/europe/day-trips-from-pienza.cfm

Axel,
This may give you some ideas http://www.slowtrav.com/italy/tuscany/hs_planning.htm

Pienza is a great place to stay.

This area is deep country, and the roads are tiny. Except close to cities, there is little traffic and much of that is farm traffic. I have whined a lot on here about driving in northern Italy but I would have no problem driving in this part of Tuscany.

Where will you pick up the car? Finding an automatic won't be easy or cheap, and as in the US sometimes you find that the rental agency doesn't actually have the car you ordered and will give you something else.

Stay south---Pienza, San Quirico, or Montalcino. The bets photo ops are in that region. Driving is not hard at all--we have done it many times. Here are some shots you may enjoy:

http://www.slowphotos.com/photo/showgallery.php?cat=3827

For a great guide contact Elena Sardelli
elenasardelli@infinito.it

She is a wonderful guide tell her I told you about her.
Will Person
Austin, TX

May is a wonderful time to stay in the area. Try to stay for at least the full 7 days.

If you fly into Rome or Florence, I recommend renting your car at the airport, where you will have no problem renting an automatic. Getting on the autostrada headed toward your destination will be easy from an airport location.

Check autoeurope.com or kemwel.com for rental options. Keep checking- prices go up and down, and even if you book at a higher price you can always get the price adjusted when it drops. Be sure to check deductibles when comparing prices. Over the past few years, I have found that Kemwel has the best prices. They are both owned by the same people and customer service is excellent.

I've stayed in the southern Tuscany area at least 6 times and usually for 2 weeks each time. Staying in the countryside at an agriturismo allows for beautiful surroundings and easy access to roads. No fighting traffic or getting confused each time you leave your base.

I always stay at Fonte Bertusi, an agriturismo located just outside of Pienza, in the most perfect and lovely location in the Val d'Orcia. They offer their guests a free GPS loaded with suggested drives, including routes mapped out on the famous white (dirt) roads that traverse the rolling hills and provide some beautiful photo opportunities. The property is owned by a local photographer and artist father and son, so they can provide great suggestions for your exploring and photography.

There is a photo contest each year for tourists visiting the area. The grand prize is a one week stay at a local accommodation. The owners at Fonte Bertusi can provide details.

<<Is it easy to pull the car off to the side at any time and stop to take pictures?>>

There are some turnouts along the main roads for pulling over. Once you get on the back roads and dirt roads, pulling over at almost any point is no problem- you will find yourself doing it regularly.

Also consider doing some hikes in the area on the white roads and tractor tracks. There are some beautiful hikes between towns/villages. It's an excellent way to capture some unique photographs.

Some of my favorite towns/villages to visit in the area-

Montisi
Castelmuzio
Petroio
Castiglione d'Orcia
Rocca d'Orcia
Sarteano
Radicofani
Lucignano d'Asso (have a simple 15 euro lunch of local cold meats, cheeses and wine at the small alimentari, located at the end of the village near the old church. Especially nice on a sunny day when you can eat outside. Highly recommended)
Trequanda (Trattoria Il Conte Matto is nice for lunch)
Monticchiello
Montefollonico (lunch at Osteria La Botte Piena. Owned by a brother/sister, the food is great and the local wine offerings are expansive)
Cetona
Citta d. Pieve (Saturday is market day)

Further south (1 to 1.5 hour drive)-

Piancastagnaio
S. Fiora
Roccalbegna
Sorano (have lunch at the beautiful and inexpensive Cantina L'Ottava Rima, located within a cave in the town. Open weekends only. Local simple food, cold meats, cheeses, beers, wine- one of my favorite places to eat in southern Tuscany)
Pitigliano

Favorite sights-

Abbazia d. Monte Oliveto Maggiore
Abbey S. Galgano (I love it! Fantastic photo opportunities. Located southwest of Siena. Google for more info)
La Foce garden tour
Bosco della Ragnaia (an enticing park cut out of the landscape by artist Sheppard Craig, located just north of San Giovanni d'Asso)

Great driving information-

http://www.slowtrav.com/italy/driving/index.htm

I will be staying at Fonte Bertusi in May. Maybe I'll see you there!

I forgot to include the link to Fonte Bertusi-

http://www.fontebertusi.it/eng/

Thanks everyone for all the great suggestions. I'll do more research on what everyone has written.

I think your best bet for an automatic will be at the airport.

Another question ...

I used the iPhone map to see sample driving directions from Florence airport to Pienza. The sample instructions are as followed:
1. 70 feet - Turn Left onto Via Del Termine
2. 0.1 miles - take a slight right turn onto Viale Zoroastro Da Peretola
3. 350 feet - Take a slight right turn onto Viadotto Del Ponte All 'Indiano
4. 0.2 miles - Continue on Viadotto Del Ponte All 'Indiano
5. 2.1 miles - Take exit toward Fi-Pi-Li
6. 1.0 miles - Take exit for E35
7. 0.4 miles - keep left toward Roma
....

Will there be signs on the road with the street names like 'Via Del Termine', 'Viale Zoroastro Da Peretola', 'Viadotto Del Ponte All 'Indiano', etc., or the street signs will most likely only have the city names ?

I wouldn't take the FiPiLi from the airport to Pienza (especially if I wanted to take pictures). I would take the SS222 (Chianti Road)to the SR2. Make some photo stops on the 222 on the way.

FYI - Google routes it down the A1, but down the 222 if you check avoid highways. Mappy.com routes it down the A1 also (99 km).

Something has been left out of your directions. The mileage doesn't add up.

Thanks kybourbon. I'm just trying to figure out how I'll get to Pienza after arriving in Italy since I think that's where I'll base myself.

I didn't list the entire direction. There are more steps after 7. I was just curious if the signs will have the street names on them.