Re: Retirement Sailing
A couple of thoughts on this critical issue. A major consideration is how often you have to pa to sleep. In some areas (most of the world), you can anchor out every night. In fact, that is often the only choice. In other areas, (western Med and heavily populated parts of the US come to mind) you need to use a marina or at least pay for a mooring. This can really push up the cost and kill a budget. So consider where you want to cruise.
My other thought, is that it is really nice to have an emergency fund to fall back on. We cruise economically for the most part but have money available for big ticket items that are unexpected. For example, we had a $7000 hospital bill in South Africa a few months ago, not to mention the extra costs of flights to Canada. Not sure what the $500 a month people do if they lack an emergency fund when there is major engine work to be done or a sail blows out and can't be fixed.
In South Africa doing lots of boat stuff. Departure north from Cape Town around December 15th. Arrival in the Caribbean around the beginning of February, after 5300 miles or so.