Well as a constant traveller I have many tricks, so here goes....
Firstly, don't plan too much! Just have a list of places youbfeel you must visit and then I often I find just booking a flight and first couple of nights accomodation is enough. When I arrive, I check oit the locality on foot and find a coffee shop and sort out the next steps from there on my laptop. Coffee shops are great places to meet locals and get some ideas what to do from their recommendations.
Secondly, dont go crazy trying to find a flight thats a dollar less on one site than it is on another.Life is too short and you can spend hours. If its a reputable site and youre happy, just book it! There is very little price difference to choose between many of the flight booking sites. I almost always use expedia.
Thirdly, Use booking.com for hotels and make sure they have free cancellation and payment on arrival. Plans change, its your holiday!
Fourthly, join facebook groups for where youre going, there is lots of great info to be had there.
Fifth. Travel light. Whybtake loads of stuff to carry when you get very cheap laundry service where youre going. Dont carry stuff you dont need, it hinders your progress.
Sixth, stay in local areas away from tourists as much as possible, you learn and enjoy things so much more. Did you travel so far just to meet people from your own country?
Finally, I always carry a packet of cigs, a few packs of cheap coloured pencils and some colouring books as these are great ice breakers to start conversations and make new friends.
Hope this helps and have a great trip :-)
I like your style, this is how I like to travel places too. Though at the moment I need something more structured because more people are involved. But I think I'll probably just pick one main thing and roughly have ideas for how to use the surrounding time. Thanks for your inputs!