The following is a glimpse of our planning for a two month circuit in Europe. Keep in mind that our style of travel is very independent; never part of a tour group. We never check baggage and have learned to travel very light and our mantra is "Travel WHERE we can, WHILE we can."
Jain does most of the research on accommodations and we work together to put everything in a three ring binder which accompanies us on the trip. I assemble a planning worksheet with Excel for Flights, Lodging, Ground Transportation Transfers and Activities. Everything is backed up on Google Drive in a private folder in PDF format. If you are interested, I would be happy to send you an Excel template.
Our flight arrangements are almost exclusively with Delta and we use our accrued miles for free trips or upgrades. For booking accommodations we use Booking.com, HomeAway.com (VRBO) and AirBnb. Many times Jain has found the same property on more than one site and she shops for the best deal (price) or the best cancellation policy. Booking.com generally has the best cancellation and payment policies. DO NOT book with a Bank Transfer payment. You will see this often in Home Away (VRBO) and it provides you NO protection from being left out in the cold or victim of bait and switch scheme ("Oh so sorry, we had plumbing problems with the apartment you booked but we have another place for you.") You can learn more about the bank transfer situation on Trip Advisor; which, BTW has gotten more into the booking business than before. They usually show properties and refer you to one of the other booking agencies, like Booking.com
We HATE Expedia. They are great on making a deal, but if something doesn't work out, they are extremely non-responsive when it comes time to get your money back.
We have an annual travel insurance policy with Allianz. Their executive plan has great coverage for $700 for both of us. They paid off like a cash register when I hurt my leg and had to cancel our Tahiti vacation. Jain just couldn't imagine how much fun it would be pushing me through the sand in a wheel chair. I filled out a form, had the doctor sign "No Travel" and we got a check within two weeks.
Here are some links that I think you will find helpful in your planning.
Deutch Bahn (German Rail)
https://www.bahn.com/en/view/index.shtml
Tickets online – Italian Rail
http://www.fsitaliane.it/tcom-en
Flixbus (Bus travel through Europe)
Rail Europe
https://www.raileurope.com/index.html
The Man in Seat 61 (Excellent Resource for all travel; extensive web site)
We have very little experience with renting cars so won't attempt to steer you. We have used Avis and Euro Star and everything we read suggests that you make the arrangements here in the states before you get there with no cars (or only very expensive cars) available.
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