My recommendations for best cities are:
Berlin (a MUST visit) - 3-4 days
Krakow
Reykjavik
Paris
Budapest
Prague (party capital of Europe)
Other highlights:
Croatia (skip Dubrovnik, or a day trip at most)
Sicily is the nicest part of Italy, just harder to get to
Scandinavia, Stockholm or Copenhagen, are nice, but very expensive. Stockholm is out of the way for most Eurotrippers
Tallinn, Estonia is a hidden gym - medieval and modern at the same time, just our of the way, but super cheap.
For travel:
Traveling between countries is seamless. When weighing the benefits of flying vs. ground transport, remember that cheaper airlines fly to more remote airports, and you can end up spending either time or money getting back to the main city.
Factor time required into your travels. Almost every point is a 2 hour flight away, but when you factor in check in times, getting baggage and transport to and from the airport, flights are 5-6 hours of time. Quite often you can take a train or bus for a lot less money and it takes the same amount of time.
Overnight trains save you a night of accommodations, but are generally uncomfortable.
If there are 304 of you traveling, you can will find that you can book cheap hotels or apartments for less than hostels. Hostels are great for meeting people to party with, but terrible for quality of sleep. If nothing else, book a private room just for your group. One of the only times we stayed in a shared room, one of the other guys in the room had his wallet and passport stolen in the middle of the night. I used booking.com and airbnb for most of my accommodations.
Travel light - very light! Aside from Iceland, you won't need overly warm clothing in most places. You can always buy a cheap sweater at H&M if need be.
For reference, I (with my wife) did ~6 weeks through Europe.We were living in Sweden and this was the last part of our stay before heading home. We left from Copenhagen and did the following:
Reykjavik/Iceland (4 days)
Stockholm (2 days)
Helsinki (2 days)
Tallinn (2 days)
Riga (1 day)
Budapest (3 days)
Croatia (7 days down the coast)
Sicily/Pisa/Florence/Venice (10 days)
Munich (3 days)
Paris (3 days)
Manchester (1 day)
Ireland (4 days)
Goteborg (2 days)
Let me know if you have any other questions.
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