I'll be paying for the entire thing for her 60th birthday. She's the only one of her siblings never to go overseas and I've never been either. I'll have roughly $7,000 saved by June 1st, 2015, and would like to leave sometime in mid July. Not sure how long we can stay but I'm aiming for about 2 weeks.
I've heard Milan is usually the cheapest to fly into but I'm open to any suggestions. In addition, I'm looking for rather inexpensive yet decent hotels that aren't completely sketchy. If it were me alone (29/M) I'd stay at some hostels but I'd like something a bit nicer for her.
Lastly, I'm considering the Eurail pass for one country. It doesn't seem like it would break the bank and allow us to use the rail system at a relatively inexpensive cost. I may even want to splurge and add France to take her to Paris since I'll certainly have the cash, but I'm not sure.
Thanks for all of your help and suggestions!