Hi, I’m planning an 8 night roadtrip in Umbria and Tuscany with my husband. We would be going November 12th-20th. We are active, adventurous 30 year olds so trying to determine if I picked the right locations to stay in. We don’t like really big cities to stay in from our travels through Italy, even though I know November may see some more restaurants/stores closed in smaller towns.
Day 1: Fly into Florence, drive to Assisi
Assisi: 3 nights to explore Umbria. Day trips to Spello, Trevi, Spoleto, Montefalco. Plan to do a cooking class, wine tasting in montefalco, and explore! Was also thinking of maybe removing a night and adding one more to Tuscany..?
Pienza: 2 nights. Explore Pienza and head to Montepulciano and montalcino for wine tastings
San Gimignano: 2 nights. Explore San Gimignano, maybe do a cooking class. Day trip to San Miniato for the truffle festival. Go to greve in Chianti
Florence: 1 night. Stroll the city, museums. Then leave the next day out of Florence.
Obviously I’m aware the weather may be rainy most days. We have hotels booked but all have free cancellation. Do you think 3 nights in Umbria is too much for this time of year? Should I add another night to Tuscany to see Siena, for example?

Where are you flying in from, because I wouldn't fly the pond and then drive. Take a break.

Do you understand ZTL? https://www.autoeurope.co.uk/travel-...to-avoid-them/

Drink driving limits 0.05% so take care

I would include Orvieto as a place to explore in Umbria. Have been there a couple of times; once for the day while spending a week in San Quirico d'Orcia and then for a few days for our daughter's wedding. A delightful town!

Yo GC, you've chosen very well. And great advice above.
I'm hard-pressed to think of many other locations with such a variety of possible bases and daytrips. The Tuscany/Umbrian region is special that way.
Fwiw, our NY-based friend has a 'travel mantra' or rule that he tries to adhere to: always follow-up a busy day with a day of nothing but far niente.
His advice is worth pondering.
I am done. the end

By my count, you will have a total of six nights in Umbria, which is five full days.

You plan for three nights in Assisi, but you list four day trips, including a cooking class and a wine tasting; I assume you would want to spend some time exploring Assisi as well. I don't see how it's possible, even if you travel by flying carpet.

You have two nights in Pienza, and want to visit two other towns, plus (I hope) Pienza itself.

With two nights in San Gimignano, you want to do a cooking class, visit two other towns, and include a cooking class and a truffle festival.

​​​All in all, you have six nights, and 11 destinations, and possibly two cooking classes, a truffle festival, two wine tastings, and some museums. I know you're young and active, but you really need to pare this way down.

we land the 12th at 9 am so we have a full day. Our flight leaves the 20th around 6 pm so again, we would have a full morning/afternoon in Florence. The places I mentioned were some ideas, not set in stone. Trying to narrow it all down..

thank you!! I may add another day to our trip to do just that! I just spent the summer in Puglia and very much enjoyed doing far niente haha.