My wife and I will be spending 4 nights in the hill towns of Tuscany and Umbria in October. We will have spent 3 nights in Florence and one in Sienna prior to renting a car for the Tuscany/Umbria portion of our trip. We are considering staying all four nights in Cortona and using that as a base of operations, doing day trips by car. We have never been to this area, so would love some advice. Stay in one place for 4 nights or perhaps 2 in Cortona and 2 in ???. We will be returning the car to Sienna and then traveling by train to Cinque Terre. Thanks for your help.
You can either use a base town or travel place to place. The nice thing about a base is not packing and unpacking each day.
Use a GPS to make the most of your time. For best results buy one at home, learn how to use it, then pack it with you. I have a TomTom 920 but the Garmins that end with a 70 (370, 670, etc.) also come preloaded with European maps.
Just be advised: all through the hills of Tuscany and Umbria there are speeding cameras. Go the speed limit and you will be fine. These cameras are everywhere, even on the small country roads. They are designed to slow traffic down. There will be a warning sign before the camera -but they are easy to miss with all the beautiful scenery to look at. I repeat: go the speed limit!!
Montepulciano and Pienza are near Cortona so it would be easy to do a day trip to both from there on the same day. I agree that staying in one place makes it nice not to have to pack and unpack, but in my opinion, the nicest part of the day in the hilltowns is the early morning, late afternoon and evening so it would be nice to experience different ones, plus you wouldn't have to drive back to your home base. My choice to spend the night would be Assisi, Orvieto and Volterra, but there are so many great choices you will want to do some research to see which ones most appeal to you that are within the distance you want to drive. Rick's guidebooks have good info on all of these and you can see lots of photos on various websites.
I can suggest a few towns in Umbria that I throughly enjoyed: Perugia, Gubbio, Montone,and Umbertide.
I really like Tuscany but Umbria is also a great part of Italy to explore. Umbria is probably what Tuscany was 10 years ago. Train as much as you can as driving in Italy is crazy!!! Hope this helps.
Happy Travels!
We spent three weeks in Umbria and Tuscany last April and you will have an amazing time. We stayed two days in Cortona and loved it (Hotel Sabrina) but it is a bit awkward to use as a base as the town is steep and most hotels in the centre require you to park outside the walls. Great Etruscan museum and a lovely art gallery. We had a small but beautiful little apartment in Pienza for three nights and loved it as a base for touring the adjacent hill towns. (check out Antica Locanda - it is in a 13th century building) Pienza has wonderful little restaurants and a great museum and walks around the walls and it is lovely and quiet in the evenings. The traditional after dinner walk is lovely as the town is high on a plateau but flat for strolling. A very short drive from Cortona just in Umbria is Castiglione del Lago which was great on market day as there were merchants all through the pedestrian areas of town - also a very good museum and castle here. We ate and drank like kings for three weeks and my husband and I still lost 7 pounds each from all the walking and hill climbing! We dropped our rental car off in Chiusi which is quite close to Cortona, but on the main rail line and easier to drive around in if you fear driving in the larger cities like we do.