Thanks to everyone, our itinerary for our late June/early July trip is coming together. 3 nights in Venice, train to Florence, rent a car and spend 3 nights in Tuscany, then 3 nights in Florence. So, I'm looking for a good base of operations in Tuscany and thinking about San Gemi? Siena in early July is having a very busy festival so we're thinking about avoiding it...Is San Gimignagno a good base of operations for 3 days? Looking to enjoy the scenary, wine, history and people...thanks all.

Yes ! Either there or further south near Pienza--I can argue both scenarios.

San Gimi is lovely and very sleepy at night. We often found ourselves the only people out after 10! Sienna with its central piazza cafes, restaurants and children running around was busier but we felt in a good way. Have a wonderful time!

Another view - I really love San Gimignano but I think it depends upon your plans for those three days. The times I have been to San Gim my base has been in the Chianti. And I detest traveling through Poggibonsi to get there - always lost on the return home due to poorly marked roads in a business sector. So, if your plan is to visit the Chianti, I would suggest a stay in Castellina or Greve area.

If you are looking to avoid Siena's Palio, I like Bob's notion to give thought to heading toward Pienza and Montepulciano and I might also consider staying in the town of Montalcino. Very convenient for visiting the abbeys and a town devoted to Brunello.

Access to other towns is important so maybe San Gimi isn't the best... So I'm considering a base for our 3-day stay in either Pienza, Montepulciano, Montalcino or ?? What hotels/B&Bs do you recommend? Willing to pay up to $250 and want something quaint, romantic, authentic, atmospheric...thanks annealex

I love San Gimmy - but I would do it as a day trip. San Gimmy as a base might be a pain - no cars allowed in the actual town, you walk up to it and back out of it - so as a base if you have a rental car it won't be the handiest. Not impossible, but not handy either. It is a great place - BTW - to buy anything made of alabaster. I got an alabaster chess there, for something like $40 USD.

Has anyone stayed in Il Giglio hotel in Montalcino? Or il Chiostro in Pienza, I think. I need a glass of wine after reading about all of this!!

I agree that San Gim is not the most centrally located town for a base. Personally I would always pick Siena, because it is larger than the others, because I love it, and because it is the most central location for day trips in all directions.

Oh alajan, we had the EXACT same experience coming back from San Gim through Poggibonsi. And no matter how many times we did it, we ALWAYS got lost. I think you are right about "poorly marked roads in a business sector," as that was always where we felt we were going in circles, no signs, and nobody around to ask.

Other than that, we had no problems driving all over Tuscany.

Yes, both, but I prefer this one halfway between www.palazzodelcapitano.com Terrific centro location for day trips.

bobthenavigator: the hotel looks great!
Is the town pretty cool, also? I like the location/access to the other towns, too. This might be the one for us!

Annealex here again. Here's the idea:
Wake up in Venice, train to Florence, rent a car there and head to Palazzo del Capitano. Make sense? My husband, the driver, may find the train more relaxing. Is that about a 4-6 hour trip between the train and car? Thanks, all.

We got lostin Poggibonsi too! Now I don't feel so bad.

San Gimmy???! That's probably just as offensive to Italians as calling California "Cali" or San Francisco "San Fran". Locals don't usually like it.

I'm sure that's true, Dayle, but I no more call it "San Gim" when I am speaking than I say "LOL" or "IMO." Besides, it's so much FUN to say "San Jeem-een-nyan'-no"!

I went to school and lived in Italy. Many many many italians - including those that live in the town - call it San Gimmy.

Small but cool--very authentic village life---the real thing. I like it.

Lost in Poggibonsi - has a nice ring to it bookwise. Ever wonder if the Poggibonsians get tired of all of us driving through their town only to get from the Chianti to San Gim? Maybe those tricky or non-existant signs are not by chance but are instead a local scheme by Poggi's tourist bureau.

We shopped at the Poggibonsi Coop and used the ATM, for what it's worth.

annealex, the drive from Florence to Pienza is probably 1 1/2 hours if you drive straight there.

But there are so many great towns and scenic drives along the way that you could take all day getting to Pienza...but what fun.

We love doodling, stopping, shopping, taking photos, etc. that we would probably plan to have a leisurely day and arrive before dark and in plenty of time for dinner.

I also got lost in Poggibonsi!! Actually drove thru a pedestrian square unknowingly until saw the stares from pedestrians. The COOP outside Poggibonsi is great,tho.

San Simmy must be a slang thing. Just sounds wrong to me...

Does anyone know what Poggibonsi means?