ITINERARY: C.T. and Tuscany- please suggest cool towns, ruins, culture!!

Since you'll be in the area, you should check out Volterra. Close to San Gimignano and equally neat. We picked up our rental in Pisa and stopped in Volterra on our way to Siena. It was our first hilltown.

Casey,
Take a look at San Galgano http://www.italiantourism.com/news03.html
for ruins and the Val d'Orcia http://whc.unesco.org/en/list/1026
for landscapes.

If I read it right, you're arriving Tuscany afternoon of Day 3, spending the night in Siena. Day 4 is spend time in Siena (I guess that would be the morning), start driving north that afternoon to turn the car in the next day.

I don't see any time for additional cool towns, ruins, or culture. No time for Montepulciano or Cortona (they are in the opposite direction from Milan). Not really any extra time to wait until the light is right for photos.

There's the old Roman theater below Volterra. That may be what you have to settle for. It's certainly not a bad choice, and it may be your only good choice.

Hi Casey,

Here's a link to Doug's research on Malpensa Airport hotels:

Doug's Post

I didn't care much for Milan. If you dont like big cities, or the world of high fashion, i'd get out of Dodge ASAP and hear to the Cinque Terre.

We are staying at the Best Western Cavaliere Hotel. Early breakfast included in discounted internet rate & free shuttle to the airport.

Also, go to flickr.com and search for "Tuscany" to find all sorts of photogenic places you might want to check out. There are some beautiful ones of Galgano. (It's one of the sword-in-the-stone places of legend, I believe.)

I'm somewhat surprised that you leave out Florence, and hope it's because you've been here before or plan to come back there on another trip. If you've never been there, could I talk you into going to Florence by train FIRST, getting in as much of it as possible when you arrive and a full day the next, departing by train for Siena. With two days and one night there with a car you can explore the surrounding towns with time left over to enjoy the nights in Siena.

Turn in your car in Siena and take the train to the CT, changing trains in LaSpezia. Cars are nice for the countryside, but the roads often have lots of curves that slow you down and you won't want to spend all of your time driving. As a photographer you will want to hike the trails that are incredibly beautiful, as is the rest of the CT. Will remind you of the PCH at Big Sur. Sorry, one day does not do it justice. Make it your last stop of your trip (instead of the first) and you will leave for Milan relaxed and well rested, taking either the direct train from Monterosso or one that changes in Genoa.

You didn't say if the six days included your arrival and departure dates, but I assumed so. If not, you have a little more time to try something new.

By the way, take your camera to the top of the Duomo for a beautiful view of in Florence and Tuscany in the distance.

2 towns I found very picturesque were Castellina and Radda. They were absolutely beautiful in an old-world chic kind of way. They left me wishing I knew how to take good pictures as i saw tons of photo ops. Castellina is about a 40 min drive from Siena and Radda about 15 min from there. An hour or so at each would be plenty if you just want pictures or add more time if you would like to stop in a cafe or do some shopping. I did most of my trip shopping in Castellina.

"Day 3: C.T. in the am. Take a train to a car rental in Pisa, Drive South towards Siena and spend time exploring small towns a little more south of there. sleep in Siena. *some towns I'd like to see around here: Lucca, San Gimignano, Montepulciano, Cortona."

If you are picking up the car in Pisa, Lucca is close and on your way. Then you could drive to San Gimignano and end up in Siena. That sounds like a full day to me.

Montepulciano and Cortona and south and west of Siena so those would make sense for the next day maybe (and Arezzo maybe). There are other small towns south of Siena too - Pienza, Montalcino, Bagno Vignoni -

I think the other option is hit the road hard from Pisa and go all the way down the coast to maybe Grossetto or Massa Marittima - an awesome little town (1.5 hours) and start working your way east from there - and then on your next day head north to San Gimignano, Lucca, etc.

I don't think you can fit all those towns in in your allotted time - you'll just be driving non-stop! You should study some maps though to get an idea of the times -

Map is Pisa to Massa Marittima

View Larger Map

wow- you guys all have been a great help! Thank you so much for your suggestions. I'm still finalizing plans but I have a better idea of what is do-able and what is too much.

Jim- I have been to Florence twice and loved it. But this time around, I'll be skipping it and concentrating on the small towns and the true Italian culture- not the touristy version.

Much thanks to all!!
~Casey