mcsles

I would appreciate a bit of guidance in our itinerary for a September 2022 Italy vacation. Specifically we have 4 nights booked at an Agriturismo outside Montepulciano, followed by 5 nights in Montefalco, Umbria. We will most likely rent a car on Saturday departure in Bologna and drive towards Montepulciano. We have previously visited Florence, Siena, Montalcino and Pienza in 2007.
Some of the towns that are of interest this trip are Volterra, San Gimignano, Cortona, Pitigliano, Orvieto and Civita di Bagnoregio.
We plan on saving a little time for the Val D' Orcia drive and Le Crete Senesi.
We really enjoy visiting a town for it's beauty and the walk through the streets, not necessarily an art museum of which I know so little about. The amazing churchs always impress and we might try to visit the Abbazia di Oliveto Maggiore.
In Umbria, we originally were looking at staying in Bevegna, however the dates of an Apartment did not work out. We currently have 5 nights at a beautiful hotel on the square in Montefalco. I recently viewed Whitehall TR on Umbria and am so excited to visit this region. My list are Todi, Spoleto, Spello, Rasiglia, Bevegna, Assisi, Gubbio, Montone and not sure about Perugia and Arezzo. The smaller towns seem to be more of interest for us.
I would value your thoughts on my list of towns and if there are others to consider instead of or in addition to.

My initial thoughts were to drive from Bologna to Cortona on Saturday. There is a market that day. Then head for Montepulciano. Perhaps drive the Le Crete Senesi etc. Sunday visit Volterra and San Gimignano. Monday visit the Abbazia and maybe Pitigliano. Save Civita and Orvieto for Tuesday.
I have used Car Rentals.com in the past and received good rates but recently looked at discover cars and they seem to be even better on price. Most company deals are asking for the return to be in Perugia. Our trip continues on south with most likely a train from Foligno headed to Positano, via Naples, Sorrento area.
Thank you all in advance for your help.

Jean

You know what interests you and where you'd like to go, but depending on your preferred travel speed and style, you will have trouble hitting everything on your list.

Bologna to Cortona to Montepulciano is about 4 hours, not counting time to rent the car, find parking on market day in Cortona, lunch?, wandering Cortona, etc. That would be a long day in the car for me. Are you flying into Bologna or coming from somewhere else in Italy? Could you train to Arezzo and pick up the car there? Or Perugia?

As to day trips, it would make geographic sense to pair San Gimignano with Volterra, but coming from your base near Montepulciano would mean close to 5 hours of driving that day... leaving almost no time to actually see the two towns. If the scenery is more important than the towns, ok. Abbazia di Monte Oliveto Maggiore is a somewhat tricky stop because it closes for a few hours in the middle of the day, so you have to head there early and move on or arrive just after the afternoon reopening which can be hard to schedule.

I like to keep day trips within about an hour's drive, so Pitigiliano paired with Sorano or Sovana and the sunken roads in this area would work for me. I would want to have most of a day in Orvieto, so I'm not sure where it fits into the time you have unless you drop SG/V. I don't see how you could also fit in Arezzo and/or Perugia other than in conjunction with the car pickup/return.

Montepulciano to Montefalco will take you along the shore of Lake Trasimeno and past Spello, so you may want to make a stop or two. If you didn't make it to Monte Oliveto Maggiore, I think you could visit Abbazia di Sassovivo on the way to Rasiglia, but check current entry details as I haven't been there in years. Don't underestimate how much time you'll want to spend in Assisi and Gubbio. The drives on secondary roads between Montefalco/Gubbio, Montefalco/Todi and Montefalco/Spoleto are very scenic.

Happy planning!

mcsles

Jean, thank you for your response. We will be in Bologna for 5 nights prior to Tuscany. When I look up pricing on rental cars, the discover car website has given me better pricing than others . In the case of Arezzo, it is double the rental fees. Perugia airport is comparable to Bologna car rental in price but actually no time savings. I am in favor of visiting the abbey in Umbria in the interest of time . I have also looked into returning the rental car in Sorrento to save the train ride from Foligno and connections. The cost was actually cheaper when adding up the train etc. Plus we get a few extra days of driving in Umbria.

Volterra may have to wait for another trip. It was just very popular in various guidebooks ,forums and TA reports. The small towns seem to excite us over the larger towns. We however would not want to miss an extraordinary site while in the region. ( like the Pont du Gard in the south of France.)
As always thank everybody for chiming in. Your knowledge is so valued.
MCS

Jean

FWIW, I found Volterra more interesting than San Gimignano and less mobbed with tours... but who knows what crowds will be like this year. You could try to see Monte Oliveto Maggiore on the way to SG.

FWIW#2... You're planning lots of driving over several days. My husband loves driving, and everything is easier now with GPS. But it's not without stress, and drives (and parking searches) usually take longer than you anticipate. (I hope you know all about ZTLs.) I suggest you prioritize your sightseeing in case things begin to fall off the schedule and try to alternate the long-drive days with short-drive days. The drive to Sorrento would be torture for me, but your itinerary is what it is.

mcsles

Jean, yes thanks I am aware of the traffic free zone for rental cars. Seems just like in France and our red light in the US. A way to steal money.

HappyTrvlr

Montefalco is very near Spello. Walk all the way to the top, or park in the lot at the top of the hill. Lots of good places to eat there too. Walk around the local streets with their beautiful flowers.We spent two weeks in Spello and loved visiting Montefalco and Bevegna several times.

mcsles

HappyTrvlr, Those three towns you mentioned along with Gubbio really seem like towns we will enjoy. After reading Whitehall TR I am really excited to see this region . Thank you for your input.

Jean

With respect, the ZTLs are not "a way to steal money." The zones are a strategy to reduce traffic, noise, pollution and damage to ancient buildings from vibrations created by traffic. Small, ancient villages were laid out to accommodate horses, carriages and carts, not cars. I applaud the various municipal governments for putting the quality of life of their citizens above the convenience of tourists, but I also think if it weren't for the zones we tourists would find the towns less appealing. So, IMO win-win.

bilboburgler

OP it is fine to have your opinions, but Italy is trying to reduce pollution and vibration in ancient town centres. Probably best to just say fine and move on with what your next question is.

mcsles

Biblioburglar, you are correct . I certainly agree with the trying to not leave such a footprint.