We stayed at dei Capitano in Montalcino. It's in the town on the wall with magnificent views over the valley below. Easily walkable to restaurants, etc. They do have a small parking lot but it's crowded and tight. Rent the smallest car possible for touring small towns in Italy.

We stayed at the Capitano in late June. It was wonderful. (Especially the pool area, which i'm not sure you'll be able to use in April.) But you get the view from the terraces when you eat breakfast or from your room. Make sure you reserve a room with a view. The view is breathtaking.

the walk into town is neglible. It's such a small place. And for some reason we were able to park our car (which we used several times) right across the street.

I have a trip report somewhere here with info on our stay in Montalcino, including restaurants, etc: "Dina4's Family Adventure: FRANCE and ITALY trip report" unfortunately, i am not sure how to give you a direct link, but if you "search" you can find it.

good luck!
dina

Yes, you could easily visit Cortona and Assisi as day trips from Siena. Cortona is a cute little place, and Assisi is better than I expected it to be!

And usually, I would recommend staying somewhere in Umbria if you're wanting to visit Cortona and Assisi. And if you're staying in San G., Siena is so close to San G., that it doesn't make sense to stay at two places so close to each other. BUT, I can understand your wanting to be able to walk through Siena in the evening, and as a more city-sized place, it definitely has a different feel at night than does San G. And I agree with you about driving on country roads in the dark - I've done it, but it's not that enjoyable, especially as I, at least, have to limit my wine intake if I'll be driving after dinner.

If you don't stay in Siena, rather than Cortona (which we have spent the night in, and it's a nice little town) or Assisi (bigger, of course), consider somewhere just a little farther south. On our last trip to Italy, last month, we spent two nights in Spello, which is just south of Assisi. It's an adorable little town, doesn't feel touristy at all, a great representative of Umbria. But you already have far too many wonderful places to visit - and I just added another suggestion!

Lex,

Au contraire! I've already been working on just such a plan.

Train from Rome to Spello. Pick up car, - 2 nights.
Drive to Montalcino---3 nights.
San Gimignano (or Siena :-])--2 nights.

Nothing's set, but it's a good possibility. Considering Hotel San Luca in Spoleto. Do you know it?

Nice to see you're thinking about Umbria!

You asked about Hotel San Luca in Spoleto, but said you were considering Spello. Those are two different towns - which one are you considering?

Most recently, we stayed in Spello, which is the smaller town of the two, just south (about 15 minutes) of Assisi. We stayed at the Palazzo Bocci (www.palazzobocci.com). Very nice place; a 4-star hotel, but prices comparable to other 3-star places we've stayed at.

Spoleto (which we visited on a different trip, some time ago) is larger, further south (about 40 min. south of Assisi, further of course from Cortona), and is best known as the site of a music festival. As I recall, I liked this town too, though it felt a little "dead" as it wasn't the festival time when we visited.

On our recent trip, we stayed 2 nights in San G., then 2 nights in Spello (stopping for lunch in Cortona on the way; we stayed overnight in Cortona on a previous trip). We drove the few minutes from Spello to Foligno, then took the train to Rome - it worked out very well, logistically.

All this research on Italy has given me "spaghetti brain"!

Not Spoleto. Spello looks good, as do Assisi and Perugia.

Ordinarily we like to be in town where we can walk to dinner. But ease of access and parking are also considerations. We're thinking we may blow the budget those 2 nights and stay at a nice resort with on-site restaurant. This hotel seems to really fit the bill. But is it too far west for touring Spello, Assisi, etc.?
http://www.hotel-vannucci.com/
We would train into Chiusi if we stayed here.

IMHO, yes, that hotel is not in a great location for what you want to do. It's almost as far west as Siena, and not close to the other cities. Mappy.com says it's a little over 1 hour from Citta della Pieve to Assisi; Cortona would be further. One of the beautiful things, I think, about Umbria, is that unlike Tuscany, which (totally generalizing) is lots of hills and hillstowns, Umbria is more like one long, north-south valley with the towns perched on the mountain to the east. Ok, I'm also generalizing about Umbria! But envision that wide valley, driving down it, and passing Assisi, Spello, Trevi, and some others I'm forgetting, all perched on the mountainside. It's a beautiful perspective (Bevagna is one of the towns in the valley itself, as is Foligono.) You wouldn't get that view in Citta della Pieve.

If you're wanting to splurge on a resort-type place, look at l'Orto degli Angeli (http://www.ortoangeli.com/), which is very close to Spello, in the beautiful town of Bevagna. We considered staying at this hotel, but decided we'd prefer to stay in a town. I've heard generally-good things about their restaurant.

We did a similar trip through Tuscany last month. Three nights in Montalcino at Il Giglio. I'd definitely get the room with the large terrace -- worth every penny. Don't be offended if the owner (the wife) gives you dirty looks. She was extremely unfriendly to us and afterwords I found other postings saying the same. But the place is great and they even valet park your car for you.

We then spent two nights in San Gimignano stopping in Siena along the way (and Monterrigioni). Stayed at Locanda Viani, just outside the town (walking distance). Definitely one of the highlights of the trip -- and also one of my favorite meals in all of Italy.

As you are going in april, could you consider not booking this part of your trip? Armed with a hotel guide such as the red michelin, you'll be able to find the prices of any hotels that take your fancy, and be able to adjust your itinerary to the places you really like.
alternatively, stay in one central spot, and use that as a base to visit all the others.