A month in Italy/Fall 2026

I'm sure you'll get a lot of answers from the more frequent Italy visitors, Tammy, and it's been a long time since I've been to Italy, but I will tell you that Assisi was one of my favorite places. I found it quite charming and loved my visit there. I also really enjoyed my time in Lake Como, which is truly beautiful.

Where do you plan to fly home from?

Good question Christine......probably Florence as we have flown out of there before. We could fly out of Milan as well.......at this point we are not sure. Depends on our itinerary.

I think after 2 weeks in Rome I would want just smaller towns/cities. Florence will be crowded- it just always is. You could day trip to Florence from Siena or Lucca.
Lots of people like Lucca (we were not that impressed) but it is an option and from there day trip to Pisa.
We went from Lucca/Pisa to Santa Margherita Ligure- loved that town- you won't see many American tourists there at all.

One of our favorite itineraries included Bologna, Ravenna, Padova, Verona then out of Milan.

It just depends how many locations you are comfortable with.

All good places you've listed. I'll add Cortona to your list as well. It's such an enchanting small village. But I also loved Siena, Volterra (easy to access Pisa from here or Lucca) and Florence (though I prefer the Santo Spirito neighborhood as it's quieter.) Maybe not much help but I don't think you will go wrong with any of those towns.

If you are open to flying out of Milan, I strongly encourage you to consider some days in Torino. It is a fabulous city and not yet very discovered by tourists and you might be ready for that as you near the end of your trip. Great food, beautiful buildings, museums, lovely areas to walk with porticoes and piazzas. As it was once the home of the Duchy of Savoy, it has royal palaces and lots of elegance.

Consider a week in Umbria.

Assisi, Gubbio, Spoleto, Orvieto, and Perugia.
https://theculturetrip.com/europe/italy/articles/the-10-most-beautiful-towns-in-umbria

We're doing the same as you, 2 weeks in Rome, but in March 2027. From there--at least as of this writing--we're planning on taking the train to Puglia on the Adriatic, basing in Lecce for a week.

Hi Tammy,

This list might be helpful since I’ve only traveled by train in Italy with just a couple of buses. Feel free to ask a question about any of them - either here or by PM.

I was planning a couple of weeks for next May and went through the process and reservations for Orvieto, Montepulciano, Cortona, Puglia, Assisi and finishing at the Spello for the festival. But the logistics without a car to go to/from Cortona, along with working around some holiday & weekend dates made it a mess. So I cancelled that plan and went with different cities. For public transportation, do not plan to take any trains in Italy on a Sunday. I know twice from experience! ; )

Okay, these are just my opinions: If you haven’t been to Siena, that’s a definite “yes”. Pisa - 1 hour is plenty unless there’s a festival, Lucca is an easy-going city.. I really like Torino - would be happy to return for the third time…. Anything along the Emilia-Romagna area is fantastic food and some exceptional art with no crowds. The Lombardy region is also full of gems. Away from the lakes, it isn’t busy. Or, if you want something completely different before or after Rome, I flew from Rome over to Palermo for five days and absolutely loved it.

Trentino-Alto Adige - 3
Moena
Castelrotto (Alpe di Siusi)
Trento

Piemonte - 2
Torino - MITO Music Festival
Asti

Lombardy - 7
Stresa (Lake Maggiore) - Music Festival
Varenna (Lake Como)
Milan
Bergamo (Citta Alta)
Cremona
Mantova
Pavia

Veneto - 4
Venice - Regata Storica Festival
Padova
Verona - Opera Festival
Vicenza

Emilia-Romagna - 5
Ferrara
Ravenna
Bologna
Parma
Modena

Liguria - 1
Monterosso al Mare (Cinque Terre)

Tuscany - 7
Lucca
Pisa - Luminara Festival
Florence
Arezzo - Jousting Festival
Siena
Montepulciano
Grosseto - Night Luminara Festival

Umbria -2
Perugia
Spello - Infiorate Festival

Lazio - 3
Rome
Fiumicino (just for the location near the airport)
Tivoli

Abruzzo - 1
Sulmona

Campania - 3
Caserta
Salerno
Amalfi

Basilicata - 1
Matera

Puglia - 9
Polignano a Mare
Bari - San Nicola Festival
Alberobello
Locorotondo
Martina Franca
Lecce
Trani
Ostuni
Monopoli

Sicilia - 1
Palermo