Hi cjm,
I agree, head to the Italian Dolomites. You will not be disappointed. They are spectacular. You could then fly out of Milan. You could rent a car (Venice) and drive north to Cortina d'Ampezzo and then west into the Alta Badia or a bit further into the Val Gardena. To drive should be about 4 hours. For a small town (with a small pedestrian zone) "in" the Dolomites, you may like Ortisei. in the Val Gardena. The Dolomite region was part of Austria until the aftermath of WWl and still retains it's Austrian "atmosphere". German is spoken as much or more than Italian here. Hence the best of food from Austria and Italy. What a wonderful thing :)
The Val Gardena is a valley that takes less than 30 min. to drive from one end to the other. The 3 towns/villages are Ortisei (largest of the 3), St. Christina and Selva, with St. Christina being in the middle. Each is just about a 5 minute drive (or bus trip) from one to the next.
Picture it like this from east to west on a map:
This is where, in my opinion, the best of the Dolomites are (east to west):
From Cortina you'd drive west about 45 minutes and come to the Alta Badia (San Cassiano, La Villa, Coravara and Colfosco). Then starts the amazing and over the top scenic Gardena Pass. After driving this pass (approx 40 min. non stop) you'll enter the Val Gardena and the first village of Selva. A few minutes later comes St. Christina and then Ortisei. After Ortisei, in about 20 minutes or so, you'll come to the A22 highway which you can take to Bolzano and eventually to Milan. You could also drive from venice on highways from Venice... to Verona, Trento, Bolzano to the Val Gardena exit on the A22. To see this route, simply go to www.viamichelin.com.
Click on Driving directions.
FROM - Venice (Venezia, Italy)
TO - 39046 Sankt Ulrich
Click "Favor highways" and then click "Get directions".
www.val-gardena.com
www.valgardena.it
If the Alta Badia may be of interest, look at:
www.altabadia.it
www.altabadia.org
We stayed once in the Val Gardena (10/03 and twice in the Alta Badia (10/06, 9/09).
Here's where we stayed and can recommend:
www.garniariston.com
www.montanara.it
The place next door to the Montanara is beautiful also and owned by the owner of the Montanara's brother.
www.tamarindo-lavilla.it/start.php?page=home&img=03&lang=EN
In case of "bad" weather, the old towns of Brixen/Bressanone and Bozen/Bolzano are well worth visiting.
www.brixen.org
www.bolzano-bozen.it/en/bolzano.htm
The "Ice Man" exhibit at the Museum of Archaeology in Bolzano is worth going to see.
www.iceman.it
The Diocesan Museum in Brixen is also worth a look:
www.hofburg.it/en/home/