Originally Posted by CaptTom
I appreciate all the different perspectives here, and the realities of the details.
I'm putting together the finances of my own plan, and I think I'm going to be OK, but my backup plan in case of unexpected expenses or just plain boredom is to find some part-time work I can do while cruising.
Generally speaking, unless you have a skill which allows you to work remotely (IT, internet based business, writing, etc.), if you are anywhere except the U.S. you will be working illegally. Be discrete and leave before you upset the locals who usually do that work legally.