There have been some great replies to this post.
I'd echo those sentiments from the Endless Travel couple about 'trying before you buy'.
I quit work in 2011 to travel the world. I used about $20k USD in savings over 12 months aimlessly wandering across about 40 countries. I bought a motorbike in London, and rode around Europe with camping gear. I camped about once very week or so - rough camping for free was a lot more difficult than I'd anticipated, and the drain on your energy of being on the road means it's better to have a roof over your head. I sold the bike and went home with about $3k in my pocket, which was enough to keep me covered until I found work.
So I lived off roughly $300 a week. I spent more in Western Europe and less in Eastern Europe obviously.
Going home what I learnt was that long term travel without a purpose isn't for me. To me, there are only so many things you can see before 'seeing things' can become tedious. Don't get me wrong, I did a lot of things that you might consider great experiences. I helpx'd on a horse ranch, and at a vineyard in Spain and learn to ride horses and make wine. I learnt martial arts in China for a couple of months. There were many things that I had wanted to do, and I got to tick them off my bucket list. However, after 12 months of being on the road, I was definitely ready to throw in this life of hedonism and go home and get back to building something of substance.
When I travel again I'll spend more time in a single country. I want to eventually speak fluent Spanish, and so I see that as a potential goal of long term, and worthy goal of travel in Spanish speaking countries. The other thing I might consider would be a goal of circumnavigating the world by motorbike - not just for the 'bragging rights' but also because forcing yourself into doing something like this puts you on a path with struggles that will lead to personal growth. They will also be more likely to lead to the development of strong bonds with your travel partner/s. Aimless wandering where you just go wherever is comfortable, and take the travel path of least resistance - to me, now, after my past experience, would be pretty fruitless and uninspiring.
For that reason, I couldn't see long term wandering as a life I would want to lead.