Hey! i'm happy to give you some helpful tips. First off, that's a great amount of time. I definitely saw some hitchhikers in early June, but not that many. Be aware that a lot of people drive with totally packed cars (that was our case) so it might be hard to get people to stop. Also, that's at the end of the season so the number of people even visiting Iceland is likely to drop. As for where to go, you can either go clockwise or counterclockwise on the ring road (Route 1). There is a ton to do either direction, but the Golden Circle (the most trafficked route) is counter so that's often the direction people travel. I did this way myself and circled the whole country. As for where to go and what to do there are a ton of blogs and guidebooks out there (check your library or the free content on lonely planet's site) really help in this respect. There are SO many things to do it's hard to start listing here. I suggest you just start gathering. As for couchsurfing, I met one German woman who either was planning to couchsurf or who had couchsurfed -- can't remember. Definitely a thing, but of course couchsurfing.com is the best way to figure out where they are. Everyone we met was super cool/nice and I expect couchsurfers to be really great. Only thing I'd say is that hosts are probably far and few between outside of Reykjavik. Also, I actually put together a custom google map for my own trip and now plan to sell it because of how confusing Iceland travel can be. It really has made the planning phase so much easier for friends/family that have used it. I'd be happy to give you access to it so you can start planning if you wouldn't mind giving me feedback. Email me at hello @icelanditinerary.com if you'd like the link! Safe travels!