Tuscany & Cinque Terre

Hi Marnie - I would suggest staying at this B&B and using it as a base of operations.
http://www.casolarelibbiano.it/
Please check out their website - Berta and Andrea,her husband, are excellent hosts - The B&B is located only about 3 miles outside of San Gimignano and easy driving to Volterra, Sienna, and Florence. The Tuscan countryside is incredible and I would suggest that you rent a car to see it as your pace! It really is easy driving in Italy - especially in Tuscany -
As far as Le Cinque Terre goes - One of my all time favorites - you could quite easily drive there but probably even easier to train it. Once you're there please walk the section from Manarola to Riomaggiore called Via Dell'Amore (lover's path)http://photo.net/photodb/photo?photo_id=7210936 It is an easy, relatively flat section , with a Cafe half way for a beverage. The scenery is beyond incredible and the total walk of that section is only about a mile. And be sure to see Vernazza - what a village - Al Castello is a restaurant directly on the harbor with excellent food and even better views. And, also the local train between the five villages allows you on and off at your descretion.
One thing Marnie - Know that whatever choice you make you will LOVE IT !!!!!!!!

Ciao, Greg

The one glaring problem I see with your itinerary is that you are doubling back a lot. Florence - Cinque Terra - Siena - and back to florence to fly out? You will be wasting a lot of time on traveling. I suggest trying to keep the doubling back to a minimum. One option would be to fly into Milan and head straight to Cinque Terre. There is a direct train from Milan to Monterosso. You can spend a couple of days in Cinque Terre and then head to Siena. Take a train to Siena spend a couple of days there, next stop San Gigmignano. Get your rental car and go stay at the agriturismo. Last stop Florence. This way you are always moving forward and not wasting time traveling back and forth between places. If you have already purchased your tickets I would have Cinque Terre be your last stop before heading back to Florence to leave. I guess this is just a long way of saying keep moving forward and keep the travel time to a minimum so you have more time to enjoy the places you are at. Enjoy your trip it sounds great.

Thanks - good idea. That is a completely different way of looking at the trip - it is helpful.

Personally, I wouldn't be all that concerned about doubling back and travel times, merely because the distances are not that great. This past october I did Florence-Bologna-Parma-Cinque Terre-pick up rental in Pisa - 8 nights in agriturismo near San Gimignano - Florence. I didn't feel like I was wasting time in transport because most of these train rides were not much more than an hour. And frankly I got such a good deal on my flight that I didn't care if I wasted an hour or two here and there in travel time. The only smart transport to and from Cinque Terre is train, they're frequent.Personally, I liked having a base in Tuscany and staying put for 8 days without having to move luggage, etc. I don't personally think you need overnight stays in either San Gimignano or Siena - I know that's an unpopular view here but I found a few hours in each city to be more than enough for my tastes, so I would say, go to the agriturismo and then go to San Gim and Siena as day trips. But, that's me, not you :) You might consider getting your car in Pisa, just because there is a better choice. we took a cheap cab from the station to the airport and it was great - no driving in any of the dreaded ZTLs (which you need to read up on before you go). Then at the end of your stay you can drive back and return the car at, say the florence airport when you're ready to leave - nice and convenient.
Otherwise I think your itinerary looks fine. 2 weeks is certainly a good amount of time to see these areas.

Marnie,

I have to agree with Scott in that it's a good idea to plan your travel between locations as efficiently as possible. Even though the distances are fairly short between all the locations you'll be visiting, two weeks is not a long time so not a good idea to waste any time.

One point to mention is that for driving in Italy, you'll need a mandatory International Driver's Permit. Visitors can be fined on the spot for failing to produce one of requested. This must be used with your home D.L. and each driver must have an IDP. You can obtain these at very reasonable cost at any AAA office (Passport-sized photos are required as well). The IDP will include information on European road signs as well. Be sure to make note of those concerning parking.

As Debra mentioned, it would be a good idea to do some research on ZTL zones. These are becoming more prevalent in many cities in Italy (especially Florence) and driving through one of the automated cameras will result in a fine (€100+ each), which are typically received several months after you return home.

You might also consider taking a GPS unit, as well as a good Map for backup (Michelin). I've found that GPS units aren't infallible but they can still be enormously helpful.

I'd suggest spending at least one night in Siena, as it has a somewhat different atmosphere at night after the "day trippers" have departed. Be sure to observe the dress code if visiting the Duomo there, as I've found they're fairly strict (shoulders must be covered regardless of gender).

For travel from Florence to Siena, Bus is a better option as it drops passengers in the main part of town rather than the bottom of the hill which is the case if travelling by train. It's quite a pleasant trip by Bus and not appreciably longer than by train.