bgleason01,Welcome to the Boards!
To begin with, I'd suggest deleting your duplicate Thread in the other section. It will be much easier to keep track of replies if they're all in the same place. I can delete it for you if you wish.
Unfortunately, your plan IS going to be somewhat complicated, due to the 4-5 month time frame. There are two reasons for that:
1.) You will NOT be able to stay in Europe for a period of 4-5 months, due to the provisions of the
Schengen Accord. Under the rules, tourists are allowed to stay
no more than 90-days in any 180-day period in the Schengen zone, which includes most of the countries of western Europe. Your Passports will be stamped when you enter and again when you leave, so the authorities will know
exactly how long you were there. EXTREME fines and deportation from the E.U. can be imposed on those who violate the rules!
There are some countries that aren't included in the Schengen zone, so you could certainly spend some time there also. Check
travel.state.gov/travel/cis_pa_tw/cis/cis_4361.html for further information.
2.) The other problem is your budget. You'll need a minimum of about US$90 per day to pay for accommodations, food, sightseeing and local transport. For a trip of five months (150 days), that will run about US$13,500 (roughly twice the amount you'll have).
For example, US$90 is about €62 at current exchange rates. A Hostel will be approximately €35 in most larger cities, which will leave only €27 for everything else. Even if you're frugal with your dining habits, that could be a problem.
As you're planning to travel with a Railpass, one other point to note is that these DO NOT include the reservation fees that are compulsory on some trains.
You'll need to pay separately "out of pocket" for those, which will reduce your expense money further.If this is your first trip to Europe, I'd highly recommend that both of you read
Europe Through The Back Door before you get too far in your planning. That will provide a LOT of good information on things like Itinerary planning, budget & money issues, transportation, sightseeing, accommodations, etc. Use country-specific Guidebooks to plan your sightseeing, etc.
You might also want to obtain an inexpensive membership with
HI Hostels. Having a membership will provide slightly cheaper rates (over non-members) and preferred booking. They have properties in most locations in Europe, and I've found that they're well run and the facilities are fairly consistent from one property to the next.
Travel in December and January may present some other problems, due to weather. You'll have to pack along more cold weather gear, and hopeufully the transportation won't be disrupted as badly next year as it was this year. There will be less crowds at that time of year, but some sights may be closed or operating under reduced hours.
It would help to have some idea where you're planning to visit?
Good luck with your planning!