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Review requested for Tuscany/Umbria component of 3 weeks in Italy

Hi, all. We are about 70 and active, planning 3 weeks in Italy.
We start by flying Chicago-Rome nonstop May 22, staying 4 nights Hotel Lancelot.
We end with a week in Venice, fly out of Venice nonstop June 13.

Looking for thoughts on the middle part where we will target Tuscany/Umbria. Thinking:
1) train to Assisi, stay 2 nights either Agriturismo le Mandrie (despite no screens, I asked them) or Hotel Umbra. Have not been to Assisi but a dear friend loves it. Are we better off staying in town or taking a taxi to & from the agriturismo ? Looks like we can’t rent a car in Assisi, I hesitate to drive from Perugia but is that being too cautious ? I have never driven in Europe.
2). Train or bus to Siena, 2 or 3 nights there, have never been but can’t go wrong it seems. Would be great to get out into some of the smaller towns on outings, have not yet looked into how best to do that. Welcome suggested itineraries for Siena time ! We love art but also landscapes, not into wine.
3) Florence 4 nights, our favorite vrbo “Simona” is booked so not sure of lodgings. A third visit, looking to fill in missed Bargello, Pitti gardens, churches.

4) train to Venice. Staying a Hotel agli Alboretti, we love it and the restaurant.

Welcome recommendations on Assisi choices and how best to use Siena time, or the rest !

Grazie, tutti -

Posted by
338 posts

In Assisi definitely stay in the town. I would stay as close to Basilica of Saint Francis as possible. I was there for 3 days and visited the basilica 3 times and that was the only way to see all of it as they had different sections of the upper and lower churches closed at different times. I really liked Hotel Sorella Luna.

Posted by
2809 posts

I would suggest staying in the town of Assisi too. The views from there are just gorgeous. We spent four nights there, which was just right for us. We also spent four nights in Siena, which gave us three full days. One day we took a bus to San Gimignano, and one day we took a bus to Monteriggiano.

Posted by
11608 posts

Add a few nights in one of smaller Chianti towns such as Castellina, Panzano, Greve, Radda. And I agree, stay in Assisi too.

Posted by
1253 posts

Would be great to get out into some of the smaller towns on outings

Will be difficult without a car, although you can look online to see if there are tour companies that offer daytrips to some places of interest to you.

Getting around Tuscany & Umbria can be done by train but they aren't going to stop at real small towns. Spend some time on the Trenitalia site to see where they go. Another drawback to the train is their schedule is your schedule. You might find that your choices are to spend 1 hour in town or 5 hours, take it or leave it. A car lets you come and go as you wish. If you get a car then scrupulously obey every speed limit and be sure you understand what ZTL's are. We've never had a problem driving.

You're welcome to ride the local buses (sometimes called "Pullman" when they go between towns) but they are intended for locals so they'll run more frequently during the hours kids go to/from school or people to/from work. Less frequently if at all on holidays and Sundays. If you're taking buses it would be a good idea to confirm the times for ones you think you will take at the TI office; few towns have a staffed bus station, it's likely just a sign on a corner in a smaller town or a parking lane adjacent to the train station in larger ones.

Without a car you are probably better off staying in town than at a agriturismo.

Posted by
7879 posts

Hi Bob,

I’m tempted to suggest this less complicated route - going to Orvieto after Rome.
Then an hour by train to Montepulciano which will get you into the beautiful smaller towns.
Siena is just an hour by train from Montepulciano, and Florence is an hour from Siena by bus. You won’t need to rent a car, and it’s gorgeous locations.