re: Italy Vacation November 2017 - May 2018 Timeframe

There's a forum on first time international travel tips. Irrespective of whether first time applies, it has some guidance on, eg, travel, flight, rail. And plenty of "tips and tricks". If I recall, a lot of the discussion seemed applicable to or Europe based.

With 2 or 3 weeks available, you should make this an Italy + 1 trip, eg, Switzerland. 18-20 days is ideal, you'll start hitting your stride day 7-10.

Book flight into any start or end point, say Rome or Geneva or even Munchen, work your way to your end destination. You may find a good deal this way and/or cover more ground.

You can "backpack" and stay in a mix of nice hostels, 2 star hotels. Very economical. Research pays off here.

Tips and tricks:
- Les Rome, more Florence
- half the clothes, twice the money

Hopefully I/we can get you some more on point info moving forward.