Tuscany/Umbria Itinerary

If you pan on visiting Bologna, you could also consider flying to Bologna, since it has a “real” airport with more flights than the airport in Florence, which by American standards would be considered just a step above a general aviation landing field.

Having said that, given your overall plan I would not bother to spend an overnight in Bologna. Thanks to the high speed train, nowadays you can reach Bologna in 36 minutes from Florence, less than many Americans’ daily one way commute to work. There is virtually a high speed train every 15-30 min connecting the two cities all day. Changing hotels takes more time than the round trip time between the two cities (pack, check out, carry luggage, travel, check in re-unpack, repack, re-check out….). You still get to enjoy the whole day in Bologna, without the hassle of changing accommodations.

For Umbria, since you’ve stayed in Orvieto already, I would consider staying either in Assisi or nearby Spello. Both are very quaint (Spello is smaller). From either you can easily drive also to Gubbio, Spoleto, etc. I’m not a big fan of Perugia. It reminds me too much of a big city (high rise apartment buildings, traffic, etc.). If you want to visit it, it has a beautiful and quaint historical center on top of the hill, but I don’t care to stay there overnight. Not even that easy to navigate with a car (if you visit, park on Piazza Partigiani and take the escalator to the top of the hill).

You are also planning to spend an overnight each in Radda and Siena. The two are very close to each other and I see no reason to change hotels in that case either. The Chianti Road (SR222) from Florence to Siena can be driven in 1h45min. Radda is about half way (a bit closer to Siena). Do you really need to bother with changing hotels 40 min apart? Choose one place and spend two nights.

And yes, I’m not fond of one nighters. I prefer to spend two nights in each hotel and day trip from there. Changing hotels, as I mentioned above, is time consuming.

Agreed
For 7 nights try to consolidate to 2 or 3 night stays at least.
Stay where driving/parking/ access by car is easiest

You have very little time planned for Umbria.

I planned a 9 day trip to Umbria for October, but cancelled due to COVID.

We had booked two nights in Orvieto then a week in Perugia using it as a base to visit Spoleto, Assisi, and more.

I suggest that you skip the trip to Bologna ( if you go there, you must also visit amazing Ravenna). spend more time in Florence and Umbria.

Thank you so much. This advice makes tons of sense. We’ll spend three nights in Firenze and daytrip to Bologna. One base for visiting Siena and Chianti also sounds like the best plan. Where should we stay? Chianti/Siena, where do you recommend to stay? We’ve been in Siena before (and adore it) but have never visited the Chianti region. Our last Tuscany trip was heavy on the Southern Tuscan wine regions of Montepulciano and Montalcino. Thanks again for all your help…much appreciated.

Thank you for your reply. I know our time is too short—any trip to Italy is always too short for my taste—but it’s all the time we have. Ravenna is stunning, but we’ve already visited it. On the other hand, my mom has never been to Bologna and would like a short visit. Wish we had more time for Umbria, but it is what it is. 😢

If you’ve stayed in Siena before, then maybe you should stay somewhere along the Chianti Road (SR 222). Radda is not on the Chianti Road, but not far from Castellina in Chianti (which is). Either town or anywhere in that area there are plenty of hotels or agriturismo, from which you can also visit Siena again (45 min away). It really depends if you prefer to stay in a small country village, or in a (smallish) city.