Tuscan Towns

You may get more pertinent advice if you tell us where you went on your first visit--and which towns you liked best.

Montepulciano, Siena, San Gimignano, Monterriggioni, Florence, Radda, Volterra, Assisi & Castellina In Chianti...but the couple we're going with haven't been to Italy so I would see whatever again but if they're are as nice as these, we'd go to different ones! Loved them all! Just thought if they didn't care, I'd try different ones, so suggestions are appreciated whether new towns or revisit these?

We had two weeks last time but only 7 days this time.

Jean

Suggest Lucca.

Do you have a flight plan? Driving, I assume? Do the friends have anything on their list, like Florence?
I really liked southern Tuscany, the Maremma region. We visited Massa Marittima, Orbetello, Pitigliano, and Vetulonia. Lots of fascinating Etruscan sites in this area.
On a previous trip, we visited Lucca and Barga. I'd add Pistoia and that would be plenty for a week. I am not the fan of Lucca that most seem to be, but I like the area.
There is so much variety packed into Tuscany, but it really depends on what the group is after.

Yes, fly into Venice and out of Rome 24 days including flight days. Lucca & Pisa are on the list prior to Tuscany; Florence is on the list; I will check out these other areas, thanks,

Jean

Jean- we did a culinary tour of Tuscany & Umbria in 2006. We enjoyed all the Tuscan towns you mentioned That said, I would enjoy revisiting most places again. In addition to your interests, we also made a stop in Cortona & Civita. We enjoyed both. Our stop in Lucca was just a few hours. Some people on the forum rave about it. Wasn’t that memorable for us.

I did a quick search on RS “Tuscany” today and found some excellent blogs & suggestions. This might be a helpful resource for your friends. ;)

We loved Spello when we visited in the summer of 2019. There is some sort of competition in town for who has their homes decorated the best with flowers, I'm not sure they would be in season in the fall. Still a beautiful town. Also Gubbio was fun. They have a funicular that goes to the top of the mountain where there is a church. It's basically a big cage that you ride up and the views are breathtaking!

We liked Pienza a lot. Also, while it is in Umbria, Orvieto is very close to Tuscany (check a map) and very wonderful.

*I just noticed that you are going to fly out of Rome, which is another point in favor of Orvieto, unless you’ve already been.

In addition to the towns you've already seen, we also enjoyed Cortona, Arezzo, and Pistoia. Volterra was my favorite (outside of Florence and Siena) so I hope you're taking your friend there.

My favorite was Montepulciano, my dental hygienist, who was living in Germany with her military husband, loves Lucca.

We liked Orvieto if you fly in or out of Rome. Lucca was only worth 1/2 day. The old town is surrounded by the city that’s so so. We stayed there fo 2 days on a tour. One day we went to see the mountains where they mine marble and half the second day was in Pisa. We walked the old town and road bikes around the wall. Some of the other hilltop towns have beautiful views over the hills and nearby options for country walks or drives. Have you considered several nights in a well located agritorisma (forgive the spelling) in the countryside? With a car you could make day trips to nearby towns, wineries, etc. Sadly we have never taken this housing option.

Take a pick
https://borghipiubelliditalia.it/en/toscana/

For me and like others above suggestions, Montepulciano! I am in love with this hilltop town and HOPE to return again later this year...fingers crossed!

If you need restaurant suggestions or places to stay, let me know. -Norman