I fly a lot to keep my airline status and will typically take one or two cheap weekend trips from LA to Europe to meet the 100,000 miles I need to fly annually. Tickets are usually only $550-$650 during the off-season - usually February is the cheapest time to go. Last year I did five days in Milan for less than $1,500 in February, including airfare and a decent hotel in the city center. Then again, I didn't do much sightseeing nor any organized tours, more just meeting with friends, walking around the city, leisure dinners, etc.
It is very possible during late January and February when airfare and hotels are cheap.
It is very possible during late January and February when airfare and hotels are cheap.

. It's a WONDERFUL little town. DH and I hope to go to Europe for our 10th anniversary (in 2012), and I definitely want to take him to Freiburg.
), Rome (definitely take the train to Pompeii while you're there), Niece, and Paris. --Katie