After 9 sailing charters in the BVIs, I've decided to look south to the Grenadines for next February's bareboat trip. I'm posting this as I am looking for an island that is easy to get to without multiple flights and changing airlines that also has a decent charter company containing a decent fleet (we're looking at a 40'- 45' monohull for 4-5 guys and not a catamaran).

I've read through a couple reviews and I suspect the questions I'm about to post have already been answered elsewhere but here goes....

Destination
I'll be flying from Canada and would like an easy to get to destination. For that reason, St Vincent had appeal as there is a direct flight from Toronto. I'd also like to skip the hassle of crossing into another country while sailing and dealing with customs. It looked like St Vincent would provide a week's worth (maybe more!) of anchorages where I could sail and not cross an international border. Any other island suggestions?

Charter Company.
All my BVI trips have been with Moorings, Sunsail and, most recently, Dream Yacht Charters. The BVIs has always had plenty of boats and its always been an option to charter something new or a couple years old. In trying to identify Grenadine companies, I've noticed Moorings and Sunsail no longer have bases at St Vincent. Without mentioning names, I've seen a couple companies with boats 10+ years old in their fleet. Old boats in charters, so I have read, run more of a risk of something going wrong, but, in all fairness, I've never chartered an older boat so I really don't know if that is actually true. Comments?

How far in advance should one book a boat for charter in the Grenadines? With fewer boats I would assume they would get booked pretty quickly. The issue is we are still working on a getting committment from the guys who will be the crew and I doubt we'll have everyone signing up for a few months yet.

Facts and opinions are welcome. PM me if you prefer.

D