Sailing around the Mediterranean, then selling your boat two years later and sailing around the Caribbean, then doing it again somewhere else is easily within t

Sailing around the Mediterranean, then selling your boat two years later and sailing around the Caribbean, then doing it again somewhere else is easily within the reach of middle-class finances. Having a boat and crew large enough, comfortable and capable enough to sail the open ocean is really the hard part, but you can get most of the pleasure while avoiding that.