1. We are going to a destination wedding in Volterra Sept. 2019
2. We have been to Tuscany twice before.
3. We are getting older and it is harder to schlep our luggage.
4. We do not want to move too many times.
5. The entire trip will be about two weeks, but we are flexible.
6. Schleping luggage up and down train steps has become a PITA.
7. Driven in Italy a number of times before, each was adventure unto itself. I understand that to get to where need to be some driving will be necessary

Initial thoughts
Fly into Milano and probably rest one night or stay three nights
Rent a car and drive to Volterra. It is a three day event but one day we might drive over to Lucca or San Gimignano, neither town we have seen.
Drive to Gubbio where we will met a relative from Spain. Stay at least two nights. Need a hotel somewhere within the town where parking cars is easy and we can walk the town.
Drive to Bologna and drop off the car. Have not been to Bologna in maybe 30 years. Length of stay undetermined. Probably one day bus trip to Parma.
Get back to Milano. There are trains and buses but are leary for the reasons stated above. Might rent a car for the day or take a cab.

Any suggestions and modifications would be appreciated.
Thank you

I am sorry I can't help much but we enjoyed day trips to both San Gimignano and Lucca.

We were in Bologna a few years ago and really enjoyed it. I think we spent three nights. Our hotel was very conveniently located right off the main square and I would recommend it: https://en.art-hotel-orologio.com. This hotel is part of a group of several hotels that all seemed to get good reviews. One highlight of our stay in Bologna was a day trip we took: https://www.italiandays.it/tour-item...logna-day-tour. It was expensive but fun and enjoyable and we thought it was well worth the splurge.

I hope these ideas help. Enjoy planning your wonderful trip!

Thank you KT.

We have visited Volterra and San Gimignano and have stayed in Lucca. They all are interesting and very different from each other. In Lucca, rent bikes and ride in the city park on top of the city walls.
In Bologna, we were so happy that we stayed at the well located Art Hotel Novecento.
In Milan we liked our hotel as it was set back from the busy streets and very quiet-Antica Locanda Leonardo near Santa Maria delle Grazia and The Last Supper. Walkable or a tram ride to the Duomo area.

We stayed here for 5 nights last year and thought it was fantastic. Loved Milan, loved the apartment, loved the neighborhood. Don't know how much it costs now or in high season, but we paid less than 100 euros a night and the place was huge and fabulous.

https://www.booking.com/hotel/it/coo...rtment.it.html

Do you want to visit Milano? Just asking because your driving times would be shorter if you flew into Florence and drove from there to Lucca, then Lucca to Volterra, etc.

In any case, I stayed at Hotel Milano Scala last month. A little bit of a cheesy vibe and a bit dark (decor too), but great location, very comfortable, good breakfast, friendly and helpful staff. Elevator to all floors if that is a concern. In Bologna I stayed at the Corona d'Oro. Central, pretty, comfortable, really accommodating staff.

Hotel Milano Scala 4 Stelle Superior Centro Milano Boutique Hotel
Luxury hotel in the center of Bologna | Hotel Corona d'Oro - Luxury 4 stars - Bologna - Italy

Thank you all.

We will visit Milano I am just sure if we will do it at the end of the beginning. The last time we visited Milano, we stayed in the countryside for a few days. On the way back to the airport, I got lost. I asked an old guy with a shotgun and no teeth in which direction was the airport. He sent us to a tiny local airstrip. Then we ran into a 1,000 bike race and were they cursing me as I past them.

But we did buy a cake in Milano which we brought to the family and friends for a treat.

We noticed an underground car park near the bus stop at the square in Volterra, very convenient to avoid schlepping of luggage. We stayed right there at the square, wonderful rooms in Camere Renzi CAMERE RENZI nicer than it looks.

Adelaidean

Thank you. I will keep that car park in mind. We will be offered a few places in Volterra where we can stay at our expense.