Hill towns recommendations (traveling from Cinque Terre to Assisi, then Rome)

Hi It sounds like a wonderful trip. I would consider Orvieto as it is easy to reach by train. You are backtracking from Cinque Terre to Assisi. Orvieto is easily reached from Rome.

Our favorite hill town is Montepulciano, second would be Pienza
Neither is easily accessed by train and I don’t think Volterra has train access either

Have not been to Orvieto but that is probably your best bet (Orvieto is Umbria, not Tuscany)
But as mentioned above maybe go to Assisi from CT then Orvieto then Rome

I like to use Rome2rio.com to check transpo options

Hi Terry,

The best location to train to a small beautiful Italian Hill town would be either to Arezzo or Perugia coming from the Cinque Terre region. You can train there, then from either town head to Assisi. It's a short commute by train to Assisi from either town. Transportation wise, this would be the most efficient and convenient for you.

I would check into how open things are in the Cinque Terre in late October/early November (not sure when your dates would have you there).

There is no train station in San Gimignano. There is a train station in Certaldo, which has a small and attractive upper old town. You can reach San Gimignano via a short bus ride from here.

There is a train station at Montepulciano Stazione. From here, a short bus ride to Montepulciano. From Montepulciano there is a bus line which runs to Pienza (number one in my books), San Quirico and Montalcino.

Camucia train station is a very short bus ride from Cortona.

Skip Orvieto this time, you only have 3 nights in Rome.

I'd recommend checking the populations of recommended places on Wikipedia (or elsewhere) to be sure they match your definition of "small hill town". I've been to and enjoyed many of the suggestions posted, but they are not all necessarily what I think of as "small". Arezzo, for example, has a population of nearly 350,000 (over 10 times the size of Assisi). Orvieto's closer to 20,000. It's beautiful, but even it may be larger than you're thinking.

Be sure to see the upper part of Assisi, which was blissfully quiet at the time of my 2015 visit, despite the heavy visitor load down near the basilica.

Thanks for the opportunity to jump onto www.trenitalia.com and dream of traveling by train again in Italy!

Some thoughts: you might want to consider spending your first night in Varenna unless you have a reason to be in Milan. It is nice to not need to change hotels that first jetlagged morning, too! This would give you an extra day to spend elsewhere.

Since train travel time is a consideration, Arezzo-to-Assisi is 1.5 hours. Arezzo is a city, but walk up to the medieval section for the smaller town feel. I attended their jousting festival and stayed in B&B De’Montetini in that neighborhood- friendly host with fantastic dining recommendations.

The longest travel will be leaving Cinque Terre to arrive at the next destination. Thoroughly check the on-line info about CT to determine what trails and boats would be open and running after Summer to make sure it’s worth your time. Otherwise, that opens your possible itineraries much broader for other towns in Italy between Lake Como and eventually Rome.

One note: don’t drop any towns off of your list before checking the actual travel times on Trenitalia. Some that look physically farther away may take less time because of the faster lines.

Spello, Umbria is a beautiful hill town, great views and dining. Not far from Assisi.

The smaller towns mostly do not have train stations. Several have been mentioned as having a train station close by and then a short bus ride. While that may be true, the length of the bus ride is less relevant that the frequency that those buses run. Does you no good to be within a 10 minute bus ride between the town and the train station if the bus only runs a few times a day. So I would research very carefully if you want to consider some of these small villages without a car. It certainly could work, but don't just assume.

For the slightly larger towns that do have have train stations - the size of the town (total population, as stated on wikipedia, etc.) is less relevant than the 'old town center', which is the area you would probably be interested in. If a town has a great, small walkable old town center do you really care if there is a large, sprawling town below it.

I have been to all the towns listed and have photos of them here if you want to take a look. That's how I decide where I want to go, by looking at photos. https://andiamo.zenfolio.com/f739967755

I think Orvieto would work for what you say you are looking for.

Check Santa Margherita..on the coast..walkable..small town..great small port for day trips..train station..so lovely

We had a wonderful stay in Orvieto, and train access is easy. I posted a summary of our experience on the forum (Part 4) https://community.ricksteves.com/travel-forum/trip-reports/italy-2019-sicily-sorrento-amalfi-pompeii-rome-orvieto-tuscany-siena-florence-cinque-terre-milan

Thank you EVERYONE for all of your suggestions. Now I have tons of places to research before making a decision! I appreciate the time you took to offer me your bits of wisdom and experience,