Critique my itinerary

I guess you have been to Rome before. For Siena you won't need a car, but for the other small towns in Tuscany, it's good to have one.I would Reduce your days in Siena by one or two (no car needed in Siena). I would stay only two nights in Siena: the 14 and the 15. One full day is sufficient to see Siena. At the end of Siena visit I would rent a car and head out to Pienza or any of those small towns In the Province of Siena. Use that location as a base to visit the small towns of Tuscany, incl San Gimignano and Monteriggioni. You can visit a lot of villages in the days you have, even Volterra and the Chianti hills. Then drive to Florence and drop the car upon arrival. If you rent from Europcar they have an office on via del Gelsomino, as soon as you enter Florence coming from Siena. It's on the right almost at the intersection with Viale del Poggio Imperiale. So you don't even need to venture into driving inside Florence.

Robert, thanks a lot for your reply. I actually hate driving. I heard there's a bus service from Siena to Montepulciano and Pienza, which I'm planning to use.

I wholeheartedly second Roberto's suggestions. So much of Tuscany is inaccessible without a car. Perhaps you could travel with a driver?

I like your idea of spending a whole week in Siena - you could consider deleting Florence and day trip to Florence from Siena. I'd suggest: Pienza 15-16 Siena: 17-18-19-20-21-22 with day trip(s) to Florence Venice: 23-24-25
Barcelona: 26-27-28-29 You could break up the travel time between Siena and Venice with a stop in Bologna or another city along the train route of interest to you (spend 5 nights in Siena rather than 6.) I didn't find Lucca all that interesting so you could skip it or day trip there from Siena. It sounds like a good itinerary - not too rushed with lots of variety.

my thoughts are that i love florence as my favorite european city. i would try to base in florence and travel to siena for a couple of days then day trip from siena to san gimignano which is awesome. pienza and montepulciano make sense to me. just was in spain in october. second time in barcelona to see a soccer match. the more i am in barcelona it reminds me of paris. probably just me. the more time in florence and barcelona i think will make your trip complete. obviously venice is incredible but three days will do nicely. have fun, be safe.

Ok, I think I'll delete Lucca and spend 3 full days in Florence.
Do you think it'd be crazy to spend 4 days in Paris after Barcelona? I have free lodging there and Easyjet seems to have cheap flights from Barcelona to Paris.

Sounds like you have a plan! I think it's a great idea to spend 4 days in Paris - especially if you have lodging costs covered!

I agree that if you have free lodging, 4 days in Paris is the way to go. But be aware that Easyjet flights won't stay cheap. The price goes up closer to the flight, and the flight can sell out. So, if you want to do this, book as soon as you can commit to a specific flight. To find all your flight options, use http://www.skyscanner.com/. Taking a quick look, I see Vueling, Ryanair, Easyjet, and Iberia all fly this route. Be aware that Beauvais airport (used by Ryanair) is 1.5 hours outside of Paris, and so takes more time and money to reach; Orly and Charles de Gaulle are much better.

I might have to postpone my trip till late Sept-Early October. So I'll be in Venice from 25 to 28 September and in Tuscany from 28 to 5 October.
Do you think the weather would still be nice by then? Even in the hilltowns? I can't research weather history for Pienza and Montepulciano.

We've been in Italy late September to mid-October and the weather has been good - even warmer than we expected. Anything can happen though - this past May we had cold and rainy weather in southern France. Have a great trip!

That's reassuring, Sharon. Thanks to everyone for their replies.

I have been to all locations except Pienza. I would stick to your original itinerary, staying in the cities you have listed so you can really experience the towns/cities without having to leave and return to a base. I like both Siena and Florence and would want to stay overnight in each city to experience the night time magic the city has to offer. I am not a fan of moving around alot any more but the towns that you have listed do not exhaust me and I feel it is the appropriate amount of time you would be spending in each place without rushing.