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Early stages of planning for Euro trip + would love suggestions

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Hi all! I am in the very beginning stages of planning a 3-month long trip to Europe summer 2015. I am looking at June, July, August, and could potentially extend my trip into September.

I've only been to Europe once before and that was two weeks in Paris + outskirts (but I do still want to go back there as I really fell in love with the city). The following cities/countries are places I definitely want to visit:

London, Madrid, Barcelona, Paris, Nice, Marseille, Bordeaux, Milan, Venice, Florence, Rome, Naples, Amsterdam, Prague

The below are places I would like to visit if it fits in the journey but am willing to pass by if it's too far off and/or would take too long:

Dublin, Lyon, Switzerland (Zurich/Geneva), Sicily, Pompeii, Pisa, Brussels, Germany (Berlin/Frankfurt), Vienna, Budapest, Athens, Sofia

I would like to make Vienna/Budapest happen if possible. Athens as well but I know it's a bit far off.

Here are a couple questions I have to get started:
- What are people's suggestions on best travel routes to minimize travel time/backtracking?
- How much time is needed for each city?
- Any cities or places that are a must-see that are not in this list?
- What are places that might be best/most fun to travel alone in? (I want to take a few weeks to myself)
- Are there any websites that can help me with planning routes on trains and stuff? One hears a lot about easy travel within Europe but I honestly do not know much about it. I was on raileurope.com which seemed pretty helpful but if there are any Bible sites I do not know about I would love to hear.
- What is the best route for weather? (I was thinking of a Dublin/London --> Amsterdam loop or vice versa but I've heard it gets hot in the summers so is there a better place to start?)

Also, I would love to hear suggestions for transportation and living as I really have not much experience with this. For ref I am early 20s/female, and have been wondering if living in hostels would be dangerous for me? I will not be traveling alone for most of the trip but wondering what an approx. price difference would be to get a cheap hotel in each city and split it between 2 or 3 people. Additionally I am not completely sure if I can pack that light (I definitely am not planning to bring two huge suitcases or anything but don't know if I can just carry a backpack, i.e.)

Budgetwise.. I would like to spend under $1000 a week excluding flight from US & back.
Please let me know if that is not doable and I will readjust expectations.

Please let me know if anything is not clear and I will try to clarify. I SO appreciate any/all advice/suggestions/input/help/etc.!!

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