Best Italian Hill Towns for One Week

The 'best of the best" depends on your criteria. My vote goes for Gubbio, Orvieto and Montepulciano. Having a car is the best because driving in Italy is my favorite thing to do. Have fun

Brendon, these are my favorites of my favorites (best of best is your decision): I love Siena, Gubbio, Assisi, Spello (about 7km from Assisi), Trevi, Todi, Cortona, Montalcino. Some of these are in Umbria, some are in Tuscany, all are easy to get to with a car, and most can be combined so you can see two in one day (although Assisi and Siena should each have a day).

I'll have to post my vote for Sienna, Orvieto and Assisi. All wonderful places! I'm sure renting a car has its benefits but, if you don't want to, we've done all three of these beautiful hill towns using trains and buses with no problem.

Some good choices (far from exhaustive): San Gimignano. I could see how it could be overrun by tourists in the summer but it is a great looking medieval town. Orvieto. It's on cliffs, has underground tunnels to tour, and a major Cathedral - much more to see than the average hill town. Also convenient to Rome and, once you're on the top, flat for a hill town. Siena is another good choice with more than the typical small hill town, especially the square and Cathedral. Volterra and Montepulciano are both classic hill towns. A short stop at Pisa isn't a bad idea while your in the area, either. A poor choice: Lucca. It's not a hill town, it's flat. There is a nice brick wall turned park. Other than the wall, the town is far from special.

Ditto what Brad said about Lucca. Nothing special. Orvieto, on the other hand, was amazing. Here are some photos I took in Orvieto in May 2011, in case you're interested.

Agreed that Lucca is not a hill town, but I quite enjoyed it.

Florence, Siena, Pisa, San Gimignano, Volterra are probably the most visited. However if you ask any native Tuscan like me to give you a list of the 10 most beautiful Tuscan towns, you will receive 100 lists totally different from each other. There are literally thousands of towns in Central Italy, most are touristically relevant. Below is an Italian website that gives guidance on the most beautiful areas of Tuscany. Take a look and take your pick. Renting a car is advised since many don't have frequent bus service. http://www.borghiditoscana.net/ Select English language and navigate the site. There is also an extensive index of towns organized by province (Tuscany comprises 10 provinces) It's probably the most complete guide Of Tuscan towns and villages. Below is another guide that specializes on the most beautiful less known towns in Italy. Click on the region you like. http://www.borghitalia.it/

Orvieto would be at the top of my list - we were just there for three nights and took a day trip to Civita di Bagnoregio! I highly recommend a visit to Civita - Rick's book has detailed directions for driving and parking to walk across the bridge to Civita. A highlight for us!

I echo Sharon's "Civita" day-trip. We were there from Pienza, which would come in second to Montepulciano among our hill towns-sorry we didn't get to Orvieto but that's for our next trip. Civita is just 30 minutes away, and Lago di Bolsena just beyond that, in case you need some "water" time.

One of my favorites is Cortona- in Umbria but certainly easy to get to. Montepulciano, Orvieto and Volterra get my vote as well. If you are driving and do not have GPS a good Michelin map is a must and we got the area road map at the tourist info's big help with back roads which we liked to do in getting to the next town. With only 7 days you will probably take the quickest routes.
Enjoy -

We spent a week at La Falconara in Montepulciano. The location was perfect as everything we wanted to see was no more than a hour drive from La Falconara. The owners, Alex and Ingrid were very gracious, I felt more like family then a guest. My sister-in-law and brother-in-law will be staying with them in December. www.lafalconara.it

Orvieto and Volterra get my vote. Find an agriturisimo outside of one city for 3 days and the other for 4 daysdoing day trips by auto. Orvieto is just 40 minutes by train from Rome, and there's a Hertz/Auto Europe car rental/dropoff across the street from the train station. There some incredible sights 10-20 miles to the west. Volterra is an incredible place to visit.

One I don't see mentioned here (and not sure it's considered a "hill town") is Fiesole. It's an easy day trip by #7 bus from Florence. Check out THE VIEW! (of the valley containing Florence), the monastery (an incredibly steep walk, though), the town square, the archaeology park and museum (Roman and Etruscan ruins). One of my personal favs, I've been twice.

A note on Civita. In high season, it can get crowded. When we were there in 2011, we stayed in Bagnoreio and went over the bridge in the evening and saw the town by moonlight. We walked back to the hotel and stayed. Then we saw Civita again early in the morning and stayed until late morning. By the time we were walking back, busses of people were pulling up. So we timed it right. It was fun during the day, but the night before it was so still and quiet and was also a great way to just wander the streets.

Brendon -
Cortona has my vote. We just took a two week trip to Italy, seeing Rome, Venice, Florence, and ending in Cortona. For us, it was a wonderfully relaxing way to end a rather frantic two weeks. The town is small and the main street and square are relatively flat. You can walk quite a while, past a wonderful park, with amazing views if you head out from the Piazza Girabaldi. Note, however, that much, ok almost all, of the rest of the town is really hilly - you will get a workout. The town has some wonderful restaurants and shops, and some sightseeing too. We mainly just relaxed! We can recommend the Hotel San Luca, the location is great and the rates were affordable, I think we paid 100 euros a night, which includes wifi and breakfast. Ask for a valley view. Have fun planning your trip!

I vote for Cortona, and would like to add a correction, Cortona is near the border of Tuscany and Umbria, but it is in Tuscany.