Just to give an update to the discussion thread. Haven't heard back from CYAO yet on sailing course and captain costs but I think I am now leaning towards getting the certifications through a reputable sailing school.

While there are disadvantages (less flexibility, more rigid itinerary) there are also a lot of advantages - namely one single source of accountability that is responsible for the boat, course, food etc.

I am a little reluctant to do a bareboat and hire a captain even one that is arranged by the charter company. If anything goes wrong there is potential for the Capt to blame the charter company, the charter company to blame the Capt and me left holding the bag!

Current leading candidate is Nautilus Sailing school. They operate out of Puerto del Rey and looks like they get their boats from Sail Caribe. Their itinerary have stops in Culebra and Visques, which is what I am looking for.

Their other sailing location in the Caribbean is in Grenada though. I must say, this option has peaked my interest. In part cause I have never been that far south in the Caribbean and in part cause I know one day I will want to leave the shelter of the virgin islands and sail in the Windward isles.

Anybody on this thread have experience sailing in St. Vincent and the Grenadines? Which would you choose(leaving logistics out of the mix)?