Hello Fellow Travelers-
Have you looked into helpx or couch surfing?
Hello!
I think that you will get more sound advice as far as you share some of your thoughts/interests/traveling style/destinations (if not set in stone,you have to arrive/depart somewhere right?) ,budget/specifics.
Why are you nervous exactly? For finding accomodation or transport or how you'll get around or what?
My advice would be to do as much research as possible before hand and make some draft itineraries/have some ideas of what you want to do/see/ how you can accomplish this.
You may feel free to drop any of those draft itineraries/ideas while on the spot, but my idea of enjoying a trip is not to spend a considerable portion of it arriving and scratching one's head as to what to do/where to go/ how to find one's way around , spending too much time on trivial things rather than enjoying destinations their selves...
An other important advice is : Do not try to fit in as much as possible. I know of people who arrive on one place, liked it, would really love to spend more days there, but move on out of fear they would miss something on a next destination. Then their next destinations did not appeal so much, but they wouldn't return to first destination as they feel they had to go on a third destination and so on. That said, I appreciate you would not want to spend your whole 2-3 months on one place. But no need to rush. I do not see why not to spend a good 1 week on places such as Paris or London or Athens if this is your thing...
Note that transmitting from A to B usually takes a good part of a day- not only for actual transit, but checking in/out of hotels, packing/unpacking, commuting from/to bus/train stations, airports etc, getting your bearing on new place and so on....
Do not underestimate effort needed to team up together and travel smoothly as a group too, even if this group consists of you and a couple of friends. You have to compromise different interests, traveling styles, agendas etc. I suggest to talk about this trip as much as possible and set up some rules... Not nice to travel all the way to Europe then find out that you want to visit major capital cities' sites and museum while one of your friends wants to hike the Alps or you want to party and sleep till afternoon while your friends want to wake up as early as possible and explore around or move on to an other area...



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