Help Me Decide Which Medieval Town to Visit in Tuscany

This answer might change if you are going in the summer, but my vote is for Siena --- I would have loved to have taken our kids or grandchildren to Siena at age seven! Running around the Campo, seeing the animals and people pictured on the floor of the Duomo, and discovering the various symbols of the different contrade (neighborhoods), including animals like the snail, owl, wolf, and giraffe. Also cool to park in one of the parking lots at the foot of the hill and ride escalators to the top. Nice bakeries. Both of our stays in Siena were in April.

Lucca would be my 2nd choice for a child --- there is the city wall to walk or bike on, and some medieval Romanesque churches with facades that a kid would appreciate. We stayed in Lucca one April and visited it again one November --- it was busy, but not unpleasantly so.

We visited San Gimignano on a Tuesday in late September (so, not the weekend and not the high season) and were really put off by the crowds and tour groups with loud leaders. We saw the frescoes I wanted to see and then left to have lunch as far from the center of town as we could get.

Never been to Monteriggioni or Montepulciano.

Not a problem finding English speakers in Siena or Lucca --- these are popular destinations for English-speaking tourists.

All the towns you mentioned are worth visiting. And all will be approximately 1.5 hour drive from Reggello, although Lucca is the farthest.

San Gimignano and Monteriggioni (both very close to each other) are the quintessentially iconic medieval towns (Monteriggioni is very small and not as busy and all you need is less than one hour to see, San Gimignano a bit bigger). San Gimignano is the most popular village in Tuscany, so avoid weekends to minimize tourist crowds. Visit both on the same trip.

Siena is actually a small city, and has the most to offer the visitor, so you might need a busy full day between the drive back and forth, and the visit.

Likewise Lucca is a small city. It's not technically a hill town since it's not on a hill, it's flat. It's more distant, but it's all freeway, so reachable in the same 1.5 hours like the rest.

Montepulciano is popular with the Rick Steves' folks. If you go there, you should couple it with nearby Pienza and maybe Monticchiello. They are all in the vicinity. Montepulciano has also become very popular, especially with Americans (thanks to Rick Steves also), so if you choose it to avoid the crowds of San Gimignano you will be disappointed. Montepulciano is just as popular now.

Well, of course, all of the places you mention are beautiful and worth visiting. Are you saying that you are allocating time to visit only one of these towns? If so, it really depends on what you are looking for. For medieval architecture and history, Siena might be the first choice. It is a stunning walled city on a hill. The Piazza del Campo is amazing and is where the annual horse races are held. The Duomo is stunning! And there are lots of great restaurants to choose from. Siena is filled with medieval architecture. Siena will be very crowded, though. When is your trip?

My second choice might be San Gimignano, another medieval city located on a hill. A Duomo, some lovely piazzas for hanging out and people watching, and 14 towers!

We loved Monteriggioni! We stopped here on our way to Florence from Siena; our hotel's desk clerk suggested it. It is small; there isn't as much to do, but what we loved is that it wasn't crowded at all with tourists and was so peaceful. This was in May.

We spent 3 nights in Lucca (along with 3 nights in Siena), and we love Lucca, too. Lucca has many pretty piazzas, and I think over 100 churches! Lucca is a walled city, and the walls are unique because they are very wide and contain a lovely, green walking path and bike path on the top. You can rent bikes, including wide bikes with a carriage in the back with a canopy. This is pulled by pedal power. I think they seat 4 people.

We weren't able to find parking in Montepulciano so I can't really help you there. It is a large city and very crowded.

If you want to spend more time in Val D'Orcia, then I would recommend Siena. I don't think Siena should be missed. Val D'Orcia is what most people think of when they think of Tuscany: rolling hills, hilltop villages, cypress trees, vineyards. Like I said, we love Lucca but Lucca is not in Val D'Orcia. But if you are already staying in Val D'Orcia, that might not matter to you.

I hope I didn't confuse you more.

I would suggest Sienna. The other places being mentioned are all interesting, but Sienna is unquestionably the most interesting. If you can time it to be there for a football game (soccer) or for the races, that would make a visit even more memorable.
Not too far away, children might find a visit to Orvieto and Civita di Bagnoregio to be pretty cool. In Orvieto children would enjoy the caves and related history, probably the funicular and a walk around and under Civita would be very memorable.

hey hey TiffanyTravels
when are you planning this trip and does "my family" mean only 3 with child or are more involved. the towns/cities you have mentioned can be very busy/crowds if during summer high season & HOT HOT with many people wanting to see and go to.with they being popular.
be careful with arrival and departure times, checkin 3-4pm and checkout 10-11am
we did a private tour, stopped at san gimignano and it was packed liked a can of sardines with all the tour buses, vans, private cars arriving at same times. no room walking thru the piazza, shops/cafe packed, stores have long lines just to buy something inside, line to get some gelato was out the door along the side and into the back of building. couldn't wait top get outta there.
siena was okay with crowds but it's a big area to roam around, the cathedral get busy but moves. haven't been to others, but how interested will a 7 year old be with this stuff. driving back to florence was bumper to bumper with all tours heading to back at same times. do find kid friendly stuff to do.
all drivers will need an IDP (aaa.com) before getting to italy, it is mandatory. read all the rules, laws, ZTL zones about driving in italy.
lucca ia a walled city, rent bikes, take a shoprt train ride to viareggio beach promenade with shops/restaurants/shopping, enjoy the water with different terrain of tuscany. town of collodi home of the author pf pinocchio, drive to pinocchio park, garzoni gardens and the butterfly house, fattoriaaldotto.it farm with winery/wine tasting and olive oil tasting right outside lucca, take a ride to pisa town and it's marina, the garfagnana area and the serchio river.
just a few examples of things to check out with the big area of tuscany, enjoy & have fun
aloha

Siena is a small city, as someone mentioned in a post above. However, it is spectacular. Closer to Reggello (45-50 minutes), Arezzo is also worth visiting, with some spectacular art and a beautiful medieval piazza in the highly medieval upper town--it tends to be a little less crowded. But it's not a village.

I think Lucca is what you are looking for but it seems prohibitively far away to really consider. As others have said Siena is a great city to visit, but if you are looking for something less touristy you might also look at Arezzo which is pretty close to where you are staying. Being less touristed Arezzo has a bit more of the authentic shops and restaurants and is an interesting blend of modern city that seamlessly blends into the old town as you travel (steep towards the end) uphill. There is a big lot behind the hilltown with easy parking that will bring you to the top of the hill by the cathedral. Assuming you're driving you could do a loop including Poppi - basically a small castle outpost town - as part of it. Not necessarily worth visiting on its own but a castle is always a good European site.

Sorry to add more options to your decision but I think it is worth considering,
=Tod

I spent a week in Lucca many years ago and loved it. But, it's just too far for a day trip from your base. Siena, while interesting, is a city. Neither place is a "country experience".

Consider getting an early start. Head to San Gimignano for the morning and then stop in Monteriggioni on the way back home. If the weather is nice, book a table with a view for lunch in San Gimignano.

I've not been to Montepulciano, but did visit tiny Montalcino (great wine ) along with the nearby Abbey of Sant'Antimo to attend a service in Gregorian chant by the monks.