Flying to Italy

If you fly into Venice-Marco Polo or Pisa, you will go through another country first. With the exception of Delta, that flies to Pisa directly from JFK in New York, there are no direct flights into Venice or Pisa from the U.S. Same with Florence. However, that is not a problem. Many great European carriers can get you to either of those two airports with one change in their home country. For Milan, it's a 3hr. train journey to either the CT or Venice. It's in the middle. But, there are four airlines that will fly you directly into Milan-MXP. Alitalia, Delta, Continental and American. As I stated, there are lots of airlines that will one-hop you there. Here's a link to the list. http://www.skyscanner.com/flights-to/mila/airlines-that-fly-to-milan.html

The closest international gateways to each spot would be Venice Marco Polo (VCE) and then Pisa (PSA). So fly open jaw into VCE and out of PSA.

Probably a coin flip between Milan and Venice. There are bus companies that run transfers to the Dolomites from either airport. Driving to CT is pretty easy from either city, but Milan is about 150 Km closer (to CT). http://www.viaggigardena.com/

Denise, In the same situation, I'd probably choose Milan / MXP as it's central to both of the locations you'll be visiting (although Venice would work too). In my case, there's usually greater availability of flights to MXP. Happy travels!

I would second an open-jaw itinerary flying into Venice and out of Pisa. You don't say what city you are flying out of , but for us in Las Vegas it is easiest to fly direct to London, then catch connecting flights.

Slight correction: US Airways flies nonstop from Philadelphia to Venice. Not that I'm fond of them, but we can get to the PHL airport in 20 minutes and they fly everywhere we want to go nonstop, so we keep flying with them.

Since the OP lives in Eagle River (WI), she's probably flying out of Minneapolis or Chicago. Unless there's another Eagle River.