Two weeks in Italy - recommendations please

I'm not familiar with Monte San Savino, however, I would recommend arriving in Venice and departing from Rome. The Venice flights leave for the U.S. VERY early in the A.M., and that can make transportation to the airport difficult.

A week is not long enough for Venice, Rome and the Val Gardena. Think of it: 7 nights, 3 complex places. Venice and the VG are close together. Maybe skip Rome? If you can add a week, you can do it all (more or less).
The Val Gardena is eminently doable with public transportation. Train to Bolzano, bus to Ortisei, buy a Val Gardena Pass for the duration as it includes all lifts. 3 nights Venice, 4 VG and call it done.

I agree with Laurel, one week is not enough for Venice, Rome, and Val Gardena -- you need to drop one of those or else cut back on your time in Tuscany. Regarding departure from Venice, I have Air Canada (Star Alliance) flights booked later this year, departing from Venice at 1:05pm and arriving in Newark at 8:18pm with a connection in Toronto.

Thanks you for the great information. I know we probably are squeezing everything in to a smaller than desired time table, but it is our reality. Knowing where to start and where to end up as far as our itinerary is concerned was my main question. I appreciate the advice!

Start in Venice, go to Val Gardena, then Monte San Savino, and depart from Rome. You'll be going north to south without backtracking, and you'll have the Tuscan week in the middle of your trip.

Thanks Zoe - makes sense!