Hi enpower! Given the inquisitive nature of your post, it sounds like you haven't done much if any non-vacation travel. When I say non-vacation, I don't mean not fun- in fact the vast majority of the greatest experiences of my life have happened when traveling this way. But there's something you need to know.
There's a huge difference between the two. It sounds like right now, your comfort level is staying at nice places in top tourist destinations like Hawaii, London, and Tokyo. In fact, most of the people you hear who are "traveling the world" are visiting places that aren't really vacation destinations and are doing so both to experience the true cultures of the places, and because it's damn near impossible for all but the richest of us to travel the way your describing for long periods of time.
I don't say this to insult your ambitions, and I really hope you don't take offense to what I'm telling you. But I really, really hope you consider taking another approach. I promise you that if you can let yourself be comfortable staying in hostels and on couches, you will have the time of your life. I probably take travel frugality to a more extreme level than you'd feel comfortable with, but just to put things into perspective, in the last month and a half, I've traveled through 8 countries and spent under $1000 total including flights. Every night but one (camping in northern Italy), I've slept on a bed or equally comfortable couch. I've met countless new friends, tried strange and often scary exotic foods, and had many nights where I've gone to sleep with sore cheeks from laughing at incredible shared experiences with my new friends from cultures all over the world.
I really hope you consider going that route, rather than exclusively visiting tourist destinations. You'll have an incredible adventure, learn and grow as a person more than you ever thought possible.