There will be plenty to do in Umbria during a 4 night stay. Stay 4 nights.

How about:

Four Nights Montepulciano
Three Nights Umbria. We loved Spello as a base to see Assisi, Spoleto, Montefalco, Bevagna, Gubbio (don't miss the Bucket of Bolts) and Perugia
Four Nights Prague
Three Nights Vienna

CaptCanuck - FYI - For future posts (and perhaps this problem will be fixed in the upgrades next month), leave space between your heading as it messes up the thread titles in the left-hand column when you don't and makes them difficult to read. Sometimes the editors can fix it if you send them an e-mail (forums@fodors.com). Some people will refrain from responding in order to let your post drop out of the top 50 so the board straightens back out. You might want to start a new thread and copy the answers you have here to it.

I wouldn't pick Montefalco as a base for exploring Umbria. It's in a lovely spot but not the most convenient one for getting to the farther corners of Umbria.

The Vienna v. Prague debate reminds me a little bit of the Venice v. Florence debate. I think it comes down to personal preference, and you won't know your own until you've visited both. I think there is a longer list of things to see in Vienna, but I thought the list for Prague was a little (not a lot) more intereseting.

I used Montefalco as a base and really liked it. My main reason for picking it was because the local wine -- one of the very finest produced in Italy -- is also one of the strongest. It was quite nice to just walk home after dinner!

Have you already picked out where you want to go in Umbria? Perhaps there is another town that would make more sense than Montefalco.

Also, where were you thinking of staying in Montefalco? I very much enjoyed my stay at I Frantoio Brizi. Montefalco locals like their town because it catches a breeze in summer, which is not true of some other places in the central plain.

Thanks for the advice so far everyone....and would love to hear a little more on the 3 night vs. 4 night Tuscany...and the Prague and Vienna thoughts....are we crazy if we only allow two nights for Vienna as well as it was just a last minute add on? or will I be wowed and should plan accordingly? As for Umbria, looking at Villa Zuccari right now just outside of Montefalco!
cheers,
CC

For me the problem with staying in that villa outside Montefalco is that you either eat dinner at the villa or you drive someplace else. It's not in town. Even if you don't drink wine with dinner, it still can be nice to stay right within a town. It gives you more flexibility. If one of you wants to rest while the other does a bit of shopping or writing postcards in a cafe -- that sort of thing.

Hey Capt -
We spent 3 days and 2 nights in Vienna and that worked well for us. It was a last minute addition to our trip and was all the time we had before we had to get back to the airport. We spent time at the delightful pastry shops, walked the beautiful old part of town several times, and spent most of one day at the Kunsthistorischesmuseum (sp?) DH and I love art so sitting for a long time in the Breughal room was fantastic. We do plan to return to Vienna soon, hopefully this Christmas.

But I can't compare it to Prague as I've been nearly everywhere in Czech except for Prague. We spent several days each in Czesky Krumlov and Telc and then time in eastern Czech.

I would spend the extra night in Prague. I was just in Vienna (had been once before) and Prague in October. I spent one night longer in Prague and would have liked even more time. I think Vienna is a wonderful city -- I heartily second the recommendation for the Kunsthistorisches Museum and would also recommend Schonbrunn Palace, the Hofburg, Stephansdom and Karlskirche -- but I think Prague is simply amazing.

Prague is a large city, but parts of it don't feel that way, especially Mala Strana below the Castle around Nerudova Street and Kampa Island. Also, don't miss the views of the Tyn Church from the Old Town Hall Tower; the church is one of the most stunning structures I have ever seen. Even if the line is long, don't skip St. Vitus Cathedral either; the multi-hued light projected by the sun through the stained-glass windows alone is worth a visit.