We are going to Italy in late May. We are flying into Florence Saturday morning, renting a car, and driving down to our villa 5 miles outside of Siena. Here are a few ideas I have for planning:
- Sunday we will probably rest at the villa and walk around Siena (if anything is open)
- Monday- drive through the Chianti region, visiting Radda, Greve and Castellini. Hopefully stopping at a vineyard for a tasting.
- Tuesday- Florence part 1
- Wednesday- drive up to Lucca to explore, and possibly hit Pisa on the way back to our villa (I don't care about Pisa, but my husband really wants to go)
- Thursday- Montepulciano, Pienza, Montalcino, if these can be done in a day
- Friday- Siena/open
- Saturday- check out of villa and head up to Florence to spend the day. Take train to Venice to spend the remaining three days of our vacation.
I know there are a few other towns worth seeing: Volterra, San Gimignano, Cortona, but I'm not sure if we can do it.
I hope this itinerary will provide for a good balance between cities/country and we'll be seeing what most of you would choose to see in the Tuscany region. Any comments would be appreciated! Thanks.

The Lucca/Pisa day is a long trip. I would sub San Gim. & Volterra that day. I would also add the Abbey at Oliveto Maggiore to your Montalcino day, even if you drop Montepulciano. You have both Sunday and Friday at Siena---one day will suffice. Weather may change your schedule--save the city for the bad weather day.

I have to admit I don't know the abbey at Monte Oliveto Maggiore, but "heavily restored and overpainted" (quoted from a travel guide to Tuscany) frescoes by Signorelli and Il Sodoma are not quite my thing.

Personally, I would suggest the tiny, gemlike Romanesque abbey of Sant'Antimo, also near Montalcino.

To each his own...

Thanks Bob! The only reason I have Siena on there twice is because I wasn't sure if anything would be open on Sunday. I will definitely consider the other suggestions you had- I appreciate it.

I would not expect anything to be open on Sunday in Siena - not even Monday morning. Use Sunday to take some drives in the countryside. In Southern Tuscany (around Pienza), the green winter wheat will be beautiful then, and you will see the most picturesque scenes you could imagine. Villages or farmhouses on top of hills, cypress trees dancing up a hill, umbrella pines dotting a ridge, small dirt roads you can drive or walk down with no other cars, small villages where you can stop for a lunch.

You can do Montepulciano, Pienza, San Quirico, Montalcino, and even Sant Antimo Abbey in a day - perhaps a long day. However, this area deserves more than just a trek through the villages.

Our closest friends have a second home in San Quirico, & we've spent a lot of time in Tuscany. I think the Southern Tuscany region is a lot prettier than Chianti - especially that time of year.

Do not miss San Gimignano under any circumstances. The only trick is to visit it first thing in the morning (9:00), before the hoards of day trippers arrive. Visit Volterra also, just remember that almost all stores close for a 2 hr or so lunch at 2:00.

Do not miss Sant Antimo Abbey - the setting is fantastic. It will eat up a lot of film. Try to get there to listen to one of the Gregorian chants in the abbey - it's quite something.

Buy your husband a postcard of Pisa or watch the Rick Steves video.

I have an itinerary I developed which describes my favorite drives through Tuscany, favorite villages, sites, etc. E-mail me at [email protected] if you want a copy. I've sent it to over 230 people on the internet so far.

Stu Dudley
San Mateo (San Francisco), Ca.

You've made a good start in your planning and have gotten some good advice. To perhaps make it even better (!), I suggest you get a copy of Top 10 Tuscany, one of the Eyewitness Top 10 Travel Guides. It's a handy little book that we found enormously helpful in planning our trip.

Thanks to everyone! Stu, I have that abbey on my "list", I would love to hear the chanting. I'd love to spend more time in Southern Tuscany, but since this is our first trip to Italy, we need to see the Siena/Florence area too. Too many beautiful places! Thanks for your help. I am now adamant about not going to Pisa