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Young couple traveling to Europe for first time

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My boyfriend and I are in our early 20s and want to go to Europe this summer. We will only have between 7-10 days to be away because of my work schedule. I have been on a European tour in high school, and it was great, but I have no idea about how to deal with transportation, finding a decent hotel/hostel, etc, since all of that was taken care of on my last trip. We have thought about going the tour route, but want to have freedom also. We want to go to every country of course, but realize that with our fairly short stay, we will be limited. I would love to go back to Italy, Spain, Germany, perhaps see Ireland. As "touristy" as it sounds, we want to see popular locations, not just stay in some bed and breakfast in the middle of nowhere in Ireland for a week. We would also like to keep it under $4000/person for the time we're there (including all expenses). Any advice or good resources at all would be greatly appreciated! :)

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