Tuscany trip
 

I am torn about which town to stay in in Tuscany this June. I'm spending 2 nights/days in Florence then renting a car to see Siena, San Gimi, and whatever else we can fit in. So the last 2 nights in Tuscany are in question. I've done day trips to Siena twice before, but my partner has never been.
My choices are: Siena, Lucca, or Pienza.
Any thoughts?
So i'd enjoy feedback from any and all.

It's the "whatever else we can fit in" that will determine the best choice for your base. Lucca is pretty far north and makes day trips to most of the central Tuscan hill towns a lot longer drive.

If you stay in either Siena or Pienza you will be within easy driving distance of Chianti country, Montepulciano, Montalcino, etc. Personally I would stay in Siena because it is a bit larger with more going on in the evening, more restaurant choices, etc. Especially if your partner has never been there.

Oh yes, make your decision based on what it is you really want to see and do.

Siena is a great choice because the town is interesting, has great shops and is wonderful to stroll around in and eat in...and certainly has more activity in the evening than the smaller towns...if that is what you want.

But the smaller towns are quite charming and we enjoyed staying in them very much. We very much enjoyed Castellina, Montalcino, Pienza and Greve...any would be a good choice.

Choose a location that is central to your interests to maximize your time.

OK I'll weigh in - I love Pienza but that's a totally different experience than Siena as it is tiny, but situated so beautifully in southern Tuscany. I love the area around Lucca - the town itself is a small flat version of Siena in that it is a walled city - but I think the real draw is the countryside there. I have 2 suggestions - if you've done Siena and don't care about being close to it, stay near Pienza as it offers Montalcino nearby and Bagno Vignone a tiny town the Romans built around a spa pool that is th main squre of the town with hot springs run off down the cliff where you can bathe in pools carved out by them in the rocks or simply dangle your feet in them - a needed treat as they will probably been worn out by Italy.
If you've never been to Lucca it's not near Siena either, but in the north of Tuscany not far from the coast, near Pisa. I go there often and can recommend a great small hotel in an olive grove with a view to the Med and the coastline of the Cinque Terra. It's about 15 - 20 km from Lucca over a beautiful country road. It's also for my money got the treat of Pietra Santa a tiny town (but bigger than Pienza) where Michelangelo had his studio and still the home of sculptors and students of the art - it is very near the moountains of Carrara. It has great restaurants mostly frequented only by Italians - it is thankfully not in most tourist itineraries (yet). You can also go for the day to Porto Venere the southernmost town on the Cinque Terra and take a boat that will stop at each of the villages and can be done in an afternoon as they are only about 10 to 15 minutes apart by sea.
The hotel I mentioned is run by two ex Benetton execs who speak very good English and have done the place up in nice style...its about 100 to 120 Euros a night with a wonderful homemade breakfast on their terrace. You can email me for the name as I want to keep it a semi secret as there are only 6 rooms and I want to be able to always get a reservation myself

Thank you everyone for your input. I love the description of Lucca Frstevens. It makes me realize that there must be another trip planned to focus on northern Tuscany alone.
Any advice for Siena or nearby Siena hotels or inns?

We enjoyed the Palazza Ravizza in Siena. It is within the walls and has a parking lot behind the gardens.

We had a small room in the back of the building with a huge window that overlooked the Tuscan countryside--magnificent! They also have a wonderful restaurant for dinner and breakfast is either inside or out in the garden.

However, do a search here for Siena hotels, and other recommendations will come up.

We just got back from Italy where we spent 2 days touring some of the highlights of Umbria/Tuscany and 1 full day in Florence. For Siena lodging, I also strongly recommend Palazzo Ravizza, especially with the garden view which looks out over the wall into the surrounding area. Check out their website www.palazzoravizza.it. Wonderful and historic hotel. Big rooms and bathrooms filled with antiques and wrought iron. Used to be a palace. Ask the front desk for a copy of the history sheet. Our second choice was Hotel Santa Caterina (www.hscsiena.it) which also looks very nice. We also visited Pienza, Orvieto, Montalciano and Volterra over 2 days with a private driver/guide who was fabulous. All were very nice. We had hoped to hit San Gimi too but decided to pass. These hill towns are all nice but they offer many similarities. Thus, I would caution against trying to see too much in a short period of time, especially if you're doing it on your own without a guide to show you around efficiently. To figure out which towns to see, I went to the local bookstore and found a Thomas Cook book on Tuscany/Umbria which had pictures and rated the towns on various parameters (castles, scenery, art, wineries, etc) which was very helpful in narrowing down our choices. The book also had maps which allowed me to finally get oriented as to distances. I'm sure there are other books which offer similar help.

You'll have a great time.

Dave

Thanks for the hot tip about Pallazzo Ravizza! I think it's exactly what i'm looking for. I filled out a room request for a junior double and hope for the best.
It's very helpful, Dave, to get your take on the hill towns. You already answered my question about whether or not to stress too much if i don't see all the quaint towns i keep hearing and reading about. I'll hit them the next time. Relaxing is good.