Need Help Planning Tuscany Strategy
 

My husband and I are picking up a car in Sorrento (after 4 nights in Rome and 2 nights in Sorrento) to drive to Cortona for three nights and then Siena for 2 nights, before dropping the car outside of Florence. We'll spend 4 nights in Florence and then train up to Venice for 3 nights before flying home.

Does anyone have suggestions for the best route between Sorrento and Cortona? I was thinking of perhaps stopping for lunch in Orvieto, after an early start out of Sorrento.

Any advice you can give regarding general Tuscany strategy would be helpful, too. I am thinking we'll use our Cortona base to access Assissi and other parts of Umbria, and then shift to Siena for both Siena itself and some touring in western Tuscany (e.g. Montepulciano, San Gimignano)- does this sound right, or am I kidding myself about how much we'll be able to see without being too rushed?

I think you may be kidding yourself.

My wife and I stayed outside of Montepulcino for ten days last October...it was our third trip to Tuscany and we still haven't seen it all.

OTOH, Cortona is not a bad location although we stayed at an agriturismo in the valley half way between Montepulciano and Cortona...made for an easy drive to either place.

IMHO I'd stay closer to Montepulciano because we liked the scenery and the hill towns, San G, Montalcino, Voltera etc better and there seemeed to be more to see on that side of the valley and beyond into the Val D' Orca.

You really do not have to shift to see Sienna of Florence for that matter.

Pick one place...stay there for five days and do day trips.

Its only about 75 to 90 minutes from Mopntepulcian to Florence, 45 minutes to Montalcino as well.

Regardless of where you stay you will love it!

I do think you have too many destinations -- and you're not mentioning all your Umbrian ones. So I think you need to prioritize your own personal list of what you most don't want to leave Italy without having seen.

Many people who advise on Fodor's about Tuscany and Umbria really have close to zero interest in seeing the great art masterpieces in the region. For them, Tuscany is about the scenery and the ambience of the hilltowns. I have nothing against that kind of trip AT ALL (I live on the Italian Riviera), but I'm just forewarning you that a lot of the advice you will get will not put any value on spending as much time as can be needed to really appreciate a great art city. You too may wish to let up on cultural sightseeing and enjoy the scenery. I'm not taking this trip! I'm just putting things in some perspective, because you may get a lot of response where people just hand you a Tuscan itinerary without regard for what you might most be interested in.

Some other things you should know:

Because of Under the Tuscan Sun, the town of Cortona now gets a huge influx of tourists. Many people who want to see Fra Angelico's great masterpiece there stay outside the town and day trip in.

Assisi perpetually gets huge crowds of tourists and pilgrims.

Florence and Siena are major, major art centers. For many people 1 day in Florence and 1 day in Siena is enough because they don't wish to enter museums or do more than stroll through churches. If you have a major interest in renaissance art, 4 nights in Florence is not too much.

Driving in and out of Florence as a day trip is something most people despise.

So my advice is that the first step is to decide how much time you want to spend taking in great achievements in art and architecture. It may be just a little, may be most of your time. But it gets much easier after than to know where to base and for how long.

Your trip is a little rushed, but doable. We once did a similar time allocation, which included 2 nights in Umbria and 2 nights in Tuscany. But that was partly the result of a compromise between DH and me - I gave him the 2 nights in Tuscany in exchange for 5 nights in Rome later in the trip! And we'd been to Tuscany several times previously, so felt we could go and just enjoy without feeling we "had" to do anything on a must-see list.

We've been to Cortona several times, once before Frances Mayes and once after. It's a nice town, but not too centrally located if you really want to explore Umbria. We stayed in Spello, which is more central but also much smaller than Cortona. I would stay in Spello again; there was enough to do, and enough places to eat, for the 2 nights that we were there. In Umbria, we focused on medieval and ancient Roman sights in the towns and surrounding areas, and enjoying the beauty. In Tuscany, we mostly focus on enjoying just being there, and on historical sights and architecture in the various towns (less paintings - that's what I spend a huge amount of time on in Florence and Venice).

I was surprised that I liked Assisi as much as I did, despite the crowds of people. I loved Giotti's works and the architecture of the churches in Assisi (we're not religious, so that was not an aspect of the visit for us).

Now I'm kind of rethinking my own advice - with your current schedule, you don't have a lot of time to visit Siena, San G., Volterra, and any other towns you might want to see in Tuscany. Read up on these towns, and see which of each town's attractions appeal to you the most.

I agree with most of th advice Zeppole has given you. It is really hard to get the "feel" of an Italian town or surrounding area if you are moving so frequently from one place to the next. For some people that does not bother them. For myself, it does and I personally would choose EITHER Tuscany or Umbria and base myself there for the entire 5 days you have allotted to BOTH. For instance we had one trip where we based for 9 days in Bevagna, a teeny sumptuous town in Umbria and just traveled within Umbria for that trip. Other times we have based in Montalcino, or Montepulciano and visited the Tuscan towns and countryside we wanted. There were even other times where we split our time between, say San Quirico and Cortona. As you see we have been many times and I still say there are myriad of places to see that we have not been yet. Most people, I dare say all?, will return to Italy once the "bug" has bitten them so you needn't try to do everything in this one trip. That's my opinion.