Tuscany

Do you mean a small picturesque town, or a small picturesque city? Villages can be very limited, but maybe that's what you want.

I hesitate to say it because I'm selfish and don't want it to get too popular, but Italy's best city in my opinion is Lucca. I've been there 5 times and am always happy to be back. You can spend one day riding bikes on the city wall and eating your way through the old centre of town, and other days on trips. Pisa is 30 min away, the beach at Viareggio & Forte dei Marmi is about an hour, Volterra is close, the Garfagnana is gorgeous and it's just north of Lucca. And if you missed something in Florence, you're an hour away. I'd consider staying in Volterra too.

I've been to San Gimignano and it's amazing, but not a lot to do and lots of tourists during the day. I had a friend who stayed there on gift pass in some Sheraton property and she said it was a magical place after the hoards leave (I'm sure the free luxury accommodation helped a little). If you can stay the night in a place that has a lot of day visitors, it becomes a completely different place.

Siena is also a nice place to park yourself for a bit, although I'm not sure what the day trips are (we moved on to Umbria the time we were there).

I did note back in 2000 when we drove through Colle Val d'Elsa that it looked like a village worth revisiting. Haven't made it back yet.

If you're open to branching out of Tuscany, when we were on the flight coming home from Tuscany years ago, the arty hip guy sitting next to us said "Tuscany is so yesterday. Umbria is where it's at." So the next trip we went to Perugia and I have to say it was lovely!

I hope that gives you something to start with. I don't know anything about SE Tuscany where a lot of the popular places are.

Thanks, Nickelina -
It all sounds wonderful!
It sounds like Lucca would be a good place to stay to do days trips to other towns!
Do you have any recommendations for places to stay? A favorite??

I loved Cortona. We stayed below the hilltown, however, people rave about staying in the hilltown itself. Beautiful Duomos each one with fine art. A small, quaint main street with shops and restaurants. A wonderful Etruscan museum and a religious art museum with Signorelli art which, to me, was beautiful. A short distance away is Assissi which is another amazing hilltown. You can also do a day trip to Siena. Use the Rick Steves' guide on how to enter the city and where to park.

Lucca gets my vote as well. A great spot to relax or from which to take day trips. Walking on the wall is a highlight for me, but walking around town is very enjoyable as well. Great food, beautiful cathedrals, and Puccini concerts! What else could a person want?

We stayed here at the L'Antica Bifore Guest House, run by a nice couple. Nice rooms, very clean, great location, breakfast is served at a communal table with other guests. https://www.anticabifore.com/en/

Buon viaggio!

Lucca would indeed be a great choice, but if you prefer to base yourselves closer to the Val d'Orcia I suggest Montepulciano. It's central for day trips into the countryside as well as the other charming little hill towns in the vicinity.
Someone on the forum recommended this place http://www.montorio.com/ which we booked for our own recent stay in May. It's a beautiful place just down the hill from Montepulciano and a short walk to the San Biagio church. It offers free parking, and the location made hitting the road in the morning pretty easy and straighforward. Can recommend it highly.
All of the nearby hill towns have their own particular charm, but our favorite was Pienza - it's where the 1968 Franco Zeffirelli production of Romeo and Juliet was filmed. Its medieval streets haven't changed much since then ... or since about the year 1500 for that matter. Interesting factoid: If you have a sharp eye you can pick out the villa in the valley below which was the home of Maximus in the movie Gladiator.
The old centers of most of the towns have ZTL's restricting access with a rental car but we found ample parking outside the city walls and only a short walk into the center - really no big deal.
Siena would be central for day trips to San Gimignano, Volterra and the Chianti region as well as the Val d"orcia. Parking can be a hassle however, especially during special events when things can fill up quickly. There's an underground parking lot at the train station that we used during our recent trip - cost is 2 Euros per day. You then access the center of the town via a series of escalators.
We made extensive use of the guide "Back Roads Northern Italy" during our own recent trip. Might work for you too. Can find used copies on Amazon for just a few dollars.

I completely agree with Montepulciano - for us, it is one of the best places to spend some time on vacation in Tuscany. The town is large enough that there are many excellent restaurants, great shopping and art galleries, and plenty of festivals and events. But, it is also not overrun with tourists and still is true to its authentic charm. From Montepulciano, there are so many town that can be explored, the list is endless.

For a great place to stay, try Fonte Martino (www.fontemartino.com). We found this place late last year and have already reserved again. The owners are from the US and were even featured on House Hunter International! Fonte Martino is only about a 5-6 minute drive to town, is newly renovated, and the hosts are wonderful!

If you want to stay in town, have a look at Charming Homes (www.charminghomemontepulciano.com). The host is also wonderful and has a few apartments to choose from. Breakfast wasn't included like it is with Fonte Martino, so is all depends what you are looking for in a place to stay.

Hope this helps!

hey hey bonnie
lucca gets my vote. stay within the walls, walk the piazzas. sit at cafe have a glass of vino and people watch. rent bikes to ride around. stop at tourism kiosk in center of piazza to see things to do.
apartmentslucca.com (ask if parking. find a place and email for availability)
cucina-italiana.com is a cooking school with chef paolo monti, teaches half day classes, also has accomodations. don't know if you have to attend class to stay.
luccatours.com with wanda for an intro to city.
come&seeitaly.com check the barga and garfagnana area in the hills and devil's bridge.
take a train to pisa early morning, if climbing tower need to order tickets (opapisa.it) train to viareggio maybe for lunch and walk along the beach.
the town of collodi, close to lucca, is the home of pinocchio. there is the garzoni gardens and butterfly house.
extravirginlucca.com a cooking class
fattoriaaldotto.it a winery/farm few minutes away from lucca
eatwith.com
so many things to do and not enough time. enjoy and have fun, don't forget the gelato and pizza.
aloha

You've been given some great suggestions.

I suggest you go out to Google Maps and look at the region. Your choice might be determined by the day trips you want to make.

Three distinct areas have been represented: Montepulciano in the South, San Gimignano/Volterra/Castellina in the central area and Lucca to the north. While it's just 2 1/2 hours by car from Montepulciano to Lucca via main roads, it could be a long day jaunt if you are out exploring. Staying somewhere in the middle might give you greatest flexibility.

You could also consider staying out in the country at an agriturismo. That would give you a different experience than staying in a small town. That's what we did and we had a wonderful time.

Will you be there over the weekend? You might want to check to see if there are any harvest festivals of interest while you are there and choose your home base accordingly.

We stayed just outside Greve to give us access to both Florence and Siena. On our next trip, I'm really leaning towards staying in Lucca, although we are also looking at staying somewhere in Umbria or the Piedmont region.

Hi, All - -

Thanks for all your great input! We really apprecdiate it!
So many choices!
We know it will be GREAT wherever we stay!!

San Gimignano is great. I also enjoyed Castellina in Chianti.

Depends on how small and how quiet you'd like. We stayed in Monticchiello which is about 15 or 20 minutes from Pienza and Montepulciano. It was very small and quiet, but there were three restaurants before and right inside the entrance of the village wall that added a bit of vibrancy. The walk to Pienza was really nice and not difficult. It was nice to get away from the crowds and we fell in love with the town.