Current itinerary looks like:
Fri, Apr 07 Depart Seattle 11:15am
Sat, Apr 08 Arrive in Venice 2-3pm
Sun, Apr 09 Venice
Mon, Apr 10 Venice
Tue, Apr 11 (Train to) Florence
Wed, Apr 12 Florence
Thu, Apr 13 (Train to) Cinque Terre
Fri, Apr 14 Cinque Terre
Sat, Apr 15 (Car To) San Gimignano/Sienna
Sun, Apr 16 (Car to) Tuscany villa
Mon, Apr 17 Tuscany villa
Tue, Apr 18 Tuscany villa
Wed, Apr 19 Tuscany villa
Thu, Apr 20 Car to Rome (and drop it off)
Fri, Apr 21 Rome
Sat, Apr 22 Flight Home Departs 12:05pm

I'm trying to decide if it's worth staying overnight in Sienna or San Gimignano, and if so, for 1 or two nights? I've read reports that these places are nice to experience after the daytrippers leave. If so, which would be better? I haven't been to either...I know that Sienna is bigger. I'm thinking maybe we should stay there, given that we will have just come from the Cinque Terre and will subsequently be spending 3 or 4 nights in a small town...probably in the area of Pienza. Thoughts? Cheers! Brent

I just realized that April 16th is Easter. If we stayed an extra day and night in Sienna or San Gimignono, would a lot of things probably be closed?

Can't help with your original question, except to say we had just 3 or 4 hours in Siena and wished we had more time.

Is there a reason for only spending one or one and a half days in Rome? Boy, are you shorting yourself...unless you've been there before and seen all you want to see.

I stayed 3 nights in Siena and could have stayed longer. If only because there are that many great places to eat.

Brent -- We are planning a trip with itinerary and times very similar to yours -- except we're flying into Rome on April 10th and out on the 24th. I was wondering if you had run across any good deals for lodging in Rome or Tuscany. That's the part that seems to be taking the better part of my research time! Thanks!

San Gimignano is definitely worth an overnight stay, if you appreciate the "feel" of a place and aren't just looking to see if there are enough sites to visit.

If the thought of strolling ancient streets in near silence and looking out over rooftops to lush valleys at dawn intrgues you, then stay the night in San G.

I enjoyed Siena, but found it to be too "large" for my tastes. It has more of a city feel than a town feel - it depends on what you want from the experience.

I agree with Aramis. San Gimignano is lovely and would be a pleasant evening. Siena has a lot to offer but is really a city.

BTW, if you are looking for places to stay in Tuscany, you might consider Podere Albereto south of Florence. It's a farm with two lovely apartments and the couple who run it are a delight. Your view is out over the Chianti hills. Life doesn't get any better. Their web address is http://www.greve-in-chianti.com/holi...bereto-eng.htm

Have fun.

Thanks for the recommendations. I think I'm leaning towards spending a single night in San Giminagno.

Regarding the very good question of why so little time in Rome, that's because my wife and I have both been there before seperately. We wanted to get a flavor for it again but focus most of our time on areas that either one or both of us have never been (I've never been to Florence and rest of Tuscany and she's never been to Venice, Cinque Terre and Tuscany). Cheers!