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Need Help with 7 week Europe Itinerary (Everywhere!)

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Hi Everyone!
I am looking for some help with my itinerary to Europe. My boyfriend/brother/and a friend are going to Europe from May 10 to June 30 (brother and friend will be coming from May 25 to June 21 and meeting us where ever we are at the time). That makes 51 ish days, taking into account travel days. We are all 21-23 year old university students. We originally had about 15 cities on our itinerary, but cut it down because we thought this might be too much travelling and not enjoying the places we were in. After looking at the itinerary, you may think there are still too mnay places... this is why I really need help and a push to cut it down!
We are interested in seeing the sites and experiencing culture. Churches/museums/castles are all great and we want to do that, but are excited about other activities (such as renting mopeds in itals etc.) and are having trouble finding those sorts of things.
Here is a general outline of what we think we want to do.
fly into London (2-3 days) -via eurostar - Paris (3-4 days) - via easyjet - Barcelona (3-4 days - this one may need to go... but I really want to go there!!!) - via easyjet - Venice (2-3 days) - train - Bologna (2 days) - train - Florence (2 days) - train - Rome (4-5 days) - via flight - Greece (either land in Santorini or Athens, Possibly go to Santorini, Mykonos, and Ios OR Paros) will travel between islands on ferries - 2 days in each island - Athens (3-4 days) - via Flight - Istanbul (4 days ish - I know this is the part of the trip that is so out of the way, but Istanbul is one of our main places we want to see... we are finding it is so expensive to get in and out though) - flight - Vienna OR Munich OR Budapest (3 days) - train - Prague (2-3 days) - train - Berlin (5 days) - train - Amsterdam (however many days are left...) (fly home from Amsterdam)

Another idea that we toyed around with was taking a train from Barcelona to italy via Montpellier, Nice, Monaco, Cinque terre etc. We have heard that is a beautiful area, but my boyfriend is concerned this may not be the "Europe" Experience we want. I dont know what that means so I guess it is up for interpretation. For me, it is between the French coast OR more germany/austria (maybe we wouldnt go to vienna or munich if we did this). My vote I think is for french coast...
I think this is a lot of travelling around, but it is so hard to narrow it down. We think at the end of the day we would enjoy the trip better if we did less moving around. The total we are spending on transportation works out to about 450E for the trip which is quite alot. We are students so obviously budget conscious.

There are a few questions I would like help with from this forum:

1) Opinion on the itinerary - specifically which cities to include/cut or any other suggestions for cities we may enjoy more

2) Other fun activities we can do in the places we are going... not just castles/museums but things alot the lines of renting bikes and exploring etc.

3) Any transportation options that may be cheaper. I have looked at air carriers like ryanair/ easyjet/ vuelingair/ olympic/ aegean etc. and trains are fairly cheap in italy. Specifically Istanbul - I am having problems getting in and out (from Greece, then to austria, germany or hungary) are there any ferries that could work?

4) How much can we expect to spend on hostels/hotels in various places? On hostelworld it seems like everything is per person, about $25-45 per night, and you have to put a deposit down when you book. Just by looking at hotels in Istanbul I have found cheaper ones (and they look nicer than the hostels). I guess the idea with a hostel is that you meet other people? Any other places I can look for hotels/hostels? Also, should we be booking in advance or just showing up and finding one there... I am a huge obsessive planner and this concept terrifies me... although the other travelers are fine with it..

Thanks so much for your help!!! Feel free to comment on any part of the trip that you know of, and I can piece these things together as I go.

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