Planning headaches Tuscany/Umbria

Well, first off I wouldn't adjust plans due to a monthly antique fair in Arezzo, it's a big place and the antique fair I'm sure is in the main square or some other contained location, surely there will not be 10,000 people flooding the entire town to buy a few old lamps. I would not cause myself so much angst and logistical problems over this.

Here's what someone from Tuscany told me:
It's low season and if the weather isn't great not that many buyers will be out but most of the streets in the old town centre including the magnificent Piazza Grande are filled with stalls so you won't be seeing the city at its best, that's for sure.

Chain, see if you have any interest in these villages.

Arezzo> Montevarchi. About 30 minute drive. Church of San Lorenzo, inside is the museum of Sacred Art. Casserole Museum.

Montevarchi > Castelina in Chianti 45 minutes.

Spend the night.

Castelina > San Gimignano 50 minutes. You could visit Certaldo or Montireggioni on your way there or back to Castelina.

Chani, I agree with your other source about the impact of the antique fair in Arezzo. I hit it by accident. I enjoy antique markets, so no complaints from me, but I was aware that the stalls were limiting my view of the local architecture, which is the main reason I go to most of the smaller places I visit. I just posted a similar comment on the forum about seeing L'Isle-sur-la-Sorge on market day. I ended up returning to L'Isle on a non-market day; that wasn't practical for me in the case of Arezzo.

Chani, during our recent International Group Zoom meeting, you asked me what time of year I visited Lago Trasimeno and enjoyed the poppies. The time was the middle of May 2010. As for Greve for your TBD2, you may enjoy an afternoon at a Tuscan winery. The lunch with winery tour at Verrazano was one of the nicest activities I enjoyed on that same trip in 2010. Admittedly, that was quite a while ago but their website indicates the winery is still in business and doing well. Here is a link: https://www.verrazzano.com/

Hi there, Chani,
We once rented a cottage very close to Castiglione del Lago. The location was great for day tripping, but I thought the town was rather dull. If you do stay there, you’ll be quite close to Chiusi, which has a very good Etruscan museum. We were able to take a tour into some tombs in conjunction with our visit.
Spello and Montefalco are so close to each other that they should be visited on the same day. Throw in a short stop at Bevagna, too.

Consider the Mugello, only a modest distance from Firenze through pretty countryside. It will be too early for the higher and forested areas, but Borgo San Lorenzo is a nice little city with a nifty ceramics museum, and it's the home of Fido the faithful dog. Nearby there are the towns of Scarperia, and Vicchio to see. On the way to the latter is the bridge where Cimabue met the young Giotto (they say).

Thank you to everyone. I have finally nailed down my basic itinerary, and a good thing too, since I leave in 10 days and have tons of non-travel stuff to do before that.

Venice 4N - fly into Milan and train to Venice, one of my very favorite cities in the world. No big plans. Train to . . .
Florence 3N - revisit the Uffizi, the Bargello, the Museo dell'Opera del Duomo, possible day trip by bus to Siena. Tram to airport to pick up rental car.
Castiglione del Lago 1N - spend most of the day in Montepulciano on the way from Florence
Montefalco 2N - visit Todi, Spoletto
Perugia 4N - visit Gubbio, Assisi, Arezzo
Greve 2N - maybe San Giminagno, winery visit. Return car to Florence airport by 10 am. Train from Florence to . . .
Rome 3N - so much to see, so little time, but an "extra" day because I have a 10 pm flight home.