Re: Cruising Caribbean Single-handed
I have to point out that YES once you get to the St Maarten the sailing is as easy is quoted above BUT assuming you leave from Florida and island hop down to Elizabeth harbor in the Bahamas which is pretty easy you do then have some hard sailing in front of you as you bash your way upwind and up current to St Maarten. Yes if you are prepared to wait for the weather windows AND follow the guidance in Bruce Van Sants book Passages South it is doable for a single hander but you are likely to have some testing days and nights on passage. The Mona passage being the one I would treat with the most care. Not for nothing is this often called the Thorny Path.
However once you are out to the Windwards and Leewards life is good.
Why not buy in Trini or the USVI or Martinique.