Definitely Canouan. The Grenadines are a step up from the BVI in required sailing and navigation
skills, but a very manageable step. Many long-time BVI charterers go there looking for a new experience. There are many beautiful and protected anchorages
, just a short sail apart. The Doyle cruising guide gives you everything you need to know about where to sail and how to do it without grounding on a reef.
St. Martin chartering involves more open water
sailing if you want to see the sights like St. Barth and Saba
. If you like restaurants and evenings ashore, St. Martin is best. Other than Bequia, there's not a lot of "civilization" in the Grenadines.
May should bring fairly benign weather
in both spots.
p.s. Welcome aboard!