The digital nomad freelancer lifestyle is fine, but one of the things you need to pull it off is a steady base of consulting clients already available, preferably with long term project needs, who are ok with your remote schedule.
If you go the ad-hoc elance route you'll be competing with 10/hr workers who speak English as well as you in countries with much lower CoL who do this for a living while you're scrambling to deal with flight tickets, airbnb fees and wifi drama in foreign countries. Never mind the problems of getting compensated in a timely fashion.
The second time I took an extended working vacation, I had four clients with semi-steady requirements and actually had to turn down work so I could spend as much time on the beach as possible. Way less stressful than hustling for elance/odesk jobs on a daily basis.
TLDR; first you get the clients, then you start the travel. ditch elance and use craigslist / your personal network, the lead quality will be much higher.