My wife and I are sharing a villa in Pisa with another couple in late September. Unfortunately, we only have five days so our hope is to take a few day trips to soak in as much of Tuscany as possible. We'll hire a driver and come back to Pisa each evening.

Naturally, we'll spend a day in Pisa, but there's just so much to see. We've been to Florence previously, so we'll probably skip it this time. Lucca, Siena, Greve in Chianti, San Gimignano have all been recommended, but we're open to other suggestions. Our agenda is simply to enjoy the beauty of Tuscany - the sights, culinary delights, wine and people. We're young and active, but at the same time, we'd all enjoy sitting in a Piazza for hours soaking in our surroundings (and the delicious vino).

Thanks in advance for your thoughts, advice and recommendations!

Bill

I love Lucca. You could spend a day there. Take the train from Pisa and save the money you would spend on a driver for that day. The central piazza is oval-shaped because it is built on the site of an old Roman amphitheater. There are very few cars inside the walls, so you can wander pretty freely. You will enjoy renting bikes and riding around the perimeter of the old town on top of the walls. It's a park now, with trees and grass and play structures for kids. Nice atmosphere. There's a wondeerful cheese store at one of the gates, but I can't remember how to find it. Maybe someone else here will know. Or ask the question on slowtrav.com Italy forum.

On the day you visit Greve in Chianti, stop in nearby Panzano for lunch at Oltre il Giardino and also visit the tiny hill town of Montefioralle. Panzano and Montefioralle are tiny, charming towns. The piazza in Greve is a great place for a glass of wine.

Pisa is a long way from the heart of Tuscany--why are you staying there?

Thank you all for your replies and advice thus far.

Bob, our friends won the villa in a silent auction and we were invited as their guests. We may be willing to spend a night in Siena, if its too much day travel throughout the week.

Have fun---the price seems right.
Try to include Volterra in your travels.

Bill, we spent a wonderful 4 days driving around Tuscany with our guide in 2009 - if you send me a PM I will email you my trip report.

From Pisa, most of the cities you mentioned are farther than I'd be willing to go while on vacation, even with a driver (?) and through beautiful countryside. Especially if you're young and active, wouldn't you rather be strolling around a town or sitting in a cafe drinking wine than sitting in a car?

Use google maps or the like; San G. is 1:30 from Pisa; Siena is 2:00; Greve in Chianti is 1:35. That's 3 hours of driving at the very least. Lucca is obviously close by, and fun to visit.

Consider some lesser-known places that are closer, such as Pescia, Pistoia, Collodi (home of Pinocchio), or even Carrara, source of (surprise) Carrara marble. The last is not so scenic, but interesting; if you use a satellite map to look at the Carrara. These cities are not a huge amount closer, though, as you'll see if you check google maps.

And definitely, if you want to visit the more central areas of Tuscany, spend at least one overnight in Siena (if not more)

I agree with Lexma90's suggestion to think inside a smaller geographic circle, and to her list I'll add Montecatini Terme, including the funicular ride up to Montecatini Alto. We also enjoyed the drive from Montecatini Terme to Vinci and on to Empoli, using secondary roads wherever possible.

You didn't mention the Cinque Terre, but if the weather's nice you could train to one of the towns, perhaps hike to another, have lunch and dinner before training back to Pisa. You could enjoy the wine and not worry about having to drive back in the dark.

When/wherever you drive, be aware that the BAC (blood alcohol concentration) limit for Italy is only .05 (compared to .08 in the U.S. and U.K.) and penalties are greater (not just in fines but in punishment).

http://rome.angloinfo.com/countries/italy/driving.asp

I can recommend having lunch or dinner at Ristoro Di Lamole in the tiny village of Lamole about 8 kilometres from Greve.

The restaurant, the staff, the amazing food, the gorgeous view from the patio, the bottle of Limoncello after dinner, the flirty owner and his equally flirty son...all make it worth the drive up the twisty little road.

Thank you all so much for your comments.

Lexma, I agree that may be too much time in the car, despite the beautiful countryside. We may consider starting over in Siena for a couple of days and then working our way back to our friends in Pisa later in the week. We're going to give that some serious thought.

All - If we were to spend an evening in Siena and work our way over to Pisa, do you like our choices and/or have specific recommendations? Would we be able to take trains along the way, as opposed to having to rent a car?

Ekc, not sure how to send you a private email without posting my address to the fodors world. I would
love to see your itinerary though.

Bob, you've got some awesome pics from your time in Tuscany.

Taking trains in rural Tuscany won't get you to many places. I know that some people get around the area by means of a combination of trains and buses, but my impression is that it's not so time-efficient. It sounds like you're not so interested in renting a car - that really would be the easiest way to get around.

If you're asking whether Greve in Chianti and San Gimignano are good choices to visit from Siena, or on the way between Siena and Pisa, yes, they would work. The Chianti area is beautiful, but not my favorite part of Tuscany (and Chianti is not my favorite Tuscan wine); obviously a matter of personal preference. But you could spend a nice portion of a day driving up the s222 (a road), visiting the Chianti towns, not just Greve.

San Gimignano is an easy trip from Siena, and well worth a visit. Or you could spend the night here, and visit Siena during the day. As mentioned previously, Volterra (west of San G.) is also interesting. It has a very good Etruscan museum and a good Roman theater just outside the city walls on the north side of town.

And that's not even mentioning the Brunello town of Montalcino, or Montepulciano or Pienza, all of which are south of Pienza.