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Amended trip itinerary - no car

We have decided not to rent a car to save some money and stress, so have amended our trip itinerary a bit and would like to know if anyone sees any issues with this as far as transportation/feasibility. Please also advise if you see any issues as far as being able to get a train to any of these places considering it's a holy year. We plan to go around June 19th, return about July 13th, give or take a day.

Fly into Milan: Depending on arrival time, either stay a night or go directly to Firenze by train.
Firenze: 1-2 nights, then train to
Perugia: 4 nights, then train to
Cortona: 2-3 nights - although we are considering a night at *Castiglione de Lago first. Is it close enough to walk/taxi from the city of Cortona? If so, then we would prefer to just do that as a day trip instead, but if not then will do a night there. Then train to
Arezzo: 2 nights, then train to
Sienna: 3 nights, then train/bus to
**Volterra* for 2 nights: It is my understanding that there is a train station nearby and then you have to catch a bus up to Volterra. Has anyone else done this recently and/or know of any potential issues with this? Then train to
Lucca: 3 nights, then train to
Firenze: 2-3 nights, then train back to
Milan: possibly stay last night there, depending on time of flight back to US.

Please let us know your thoughts as to any potential transport issues between these locations. We will be traveling very light, carry on only, so not worried about luggage issues, and have our reasons for wanting to do in this order, so please don't suggest changes unless you see an actual issue. Thank you in advance for your time and consideration.

Posted by
15762 posts

Not sure if this is your first time to Italy, but Florence deserves about 3 nights.
Perugia 4 nights? I would move some to Florence, unless you are using Perugia for day trips (Assisi, Spello, Gubbio, etc.)
Cortona: 2 nights is enough. Add a 3rd one only if you plan a day trip to Castiglion del Lago (by train). No, it is not walking distance.
Volterra has no train station. You can take a bus Siena-Colle Val D’Elsa-Volterra (change in Colle VE). Or a bus from Pontedera, located on the Pisa Florence train line.
You have Firenze stay split into two times. Choose one stay only and stay 3 nights.
Lucca and Siena can be easily visited from Florence on day trips (1.5 hours each way from Florence), in case you are interested. I would limit my stay in Lucca or Siena to no more than 2 nights, unless you plan to use those cities as base to visit nearby villages.

Posted by
28 posts

Ah, you are right - we still have Firenze split. We were originally planning to fly into/out of that airport, but now thinking Milan, so I'll change that.

We had planned to stay in Arezzo/Cortona that long to do a couple day trips and have time to just relax and enjoy the places.

We really wanted to see Volterra, but may need to scratch that idea if it's going to be too crazy getting there. Google says it'll be several trains/busses, but thought to ask here in case someone has done it and knows better.

Posted by
1015 posts

I would agree on trying to consolidate your time in Florence. Nothing you're going to is far enough away to justify stopping off in Florence and then continuing on.

The complicated part of your planning is that everything is south of Florence except Lucca and together Arezzo, Cortona and Perugia are clustered to the east. No matter what order you do these towns in you'll have to come back through Florence to catch the fast train to Milan. I guess the question is where do you want to do the big city versus these small towns you're also scheduling. In beginning, middle or end?

In broad strokes I think you need to do the three eastern cities together and Siena, Florence and Lucca together with Florence being the obvious outlier of the big, busy city with tons of agenda items and things to see and do while the others are more much explorations of medium sized and smaller towns.

I think I would bite the bullet and train from Milan to Florence (fast train) and then train to Perugia which will probably be 4-5 hours on the train. But this will allow you to then move northward to Cortona and onto Arezzo easily. This also places the biggest city (outside of Florence) first with smaller places in between. And from there you can bus from Arezzo to Siena in about an 1:15 spend several days in Siena and then finally tackle Florence. (If you do end up going from Siena to Arezzo or vice versa there is a 1:15 bus that connects them which is faster and more direct than either of the train options.) Post Florence spend a few days in Lucca to experience the slower pace of Tuscan life again in a place with no hills this time. And finally train back to Florence back to Milan.

The timing is up to you - I think Florence deserves at least 4-5 nights - especially as the big city centerpiece of your trip. I can see ending your trip on either Siena or Lucca post Florence. Siena is dramatic, hilly and has some great sights but is also touristy and can be tiring. I like Lucca and would recommend a couple of nights there but it lacks "big sights" and is a quieter stop. Despite the listed population Lucca is 9-10K inside the walls and feels very much like a small town.

Notes: Volterra is difficult to get to in the best of times and it is well west of everything else you list. Arezzo, Siena and Cortona will be very hilly while Florence is flat within the city center and Lucca completely flat.

This more of a sketch of information and logistics than a plan but that's how I would think about it. I think this plan spaces the larger cities out with smaller places in between and flows best with the travel logistics you laid out.

Hope it helps, have a great trip,
=Tod