Umbria

We had a week in Montepulciano for a week before Umbria too and loved it. Did not go to Spoleto but loved the other three especially Orvieto. If you don't have a car and are depending on public transport, you should also consider Perugia.

If you really want to see the small towns then I would recommend renting a car. It is the best way to reach them and driving is easy in the countryside and I found parking to be easy in Montepulciano and all of the other hilltowns we visited.

Assisi is lovely but not a good base for touring by train as the station is a few miles out.

I really liked the towns of Montefalco, Bevagna and Spello. However, I'm not sure how these locations would be very helpful without having a car. I think you could certainly see quite a bit in Umbria without a car, but so many of our favorite towns (in addition to the above, we also really liked Deruta, Assisi and Trevi, among others) either did not have a train station, or the train station was not directly in town.

Tracy

Tracy is correct. Umbria, with the exception of Perugia, is predominatly small towns. To visit those small towns without a rental car would require lots of time and inconvenience. Please click on my initials for more information regarding Umbria than you could possible need.

Without a car, I feel that Perugia would be your best base for exploring Umbria. Perugia has a train station accessible by bus from the old/upper town and a bus station within walking distance from the old/upper town.

From Perugia, some of the towns you can visit by train or bus-

Assisi (+ a taxi or bus from train station), Spello, Trevi (+ a bus or taxi from train station), Spoleto (+ a bus or taxi from the train station), Cortona, Todi, Deruta, and Gubbio. You can also visit some towns on Lake Trasimeno (train + boat).

Without a car, it will be difficult to properly visit towns and countryside from Montepulciano.

I suggest a car for this trip. If you do rent a car, skip Perugia as a base and stay in or near Spello, Assisi, Spoleto, Bevagna or Montefalco. I actually think by using a car you will have a more relaxing, stress-free, rewarding vacation.

Loved Assisi!!!

Have dinner at Medio Evo (Via Arco dei Priori 4, www.ristorantemedioevoassisi.it). Fab food and the best gnocchi with gorgonzola that I've ever had!

Thanks for your helpful comments. We are now flying in to Milano instead of Roma due to difficulties in getting suitable dates for flights.
Would be grateful to hear comments on Milano to Montepulcione and as indicated earlier we will be trying to do that by train and bus.
We have secured accommodation with Giacomo at Politians, which is recommended by a number of Fodorites. Certainly Giacomo has been very helpful already.