Who can tell me the best Caribbean winter regattas for charters to participate in?

Richard Spindler used to publish something like this in Latitude 38. Don't know about now, haven't looked in years.

I sorted my summer plans the same way, and checking yacht options first really helped me figure out budget and vibe. I booked through yacht charter Greece and liked how easy it was to match boat size with the islands I wanted to hit. If you’re juggling dates, looking at shoulder-season prices there made choosing a week way less stressful.