This is by no means a general statement because the Caribbean is quite diverse, but I have noticed that in the sailing places where I have been rental Sunfishes have often been replaced by Hobies (like the Hobie Wave). The latter being more 'tourist friendly' (less prone to capsize). Moreover, Sunfishes that may be for hire are often in poor shape.
Curacao is a great island to visit, even if you are not a sailor. And sailing on the Spanish Water (Spaanse Water) must be quite nice. I was out on the ocean once (Curacao Regatta 2007), and it was WINDY!
in DR you can visit cabarete in the north part of the island (its called the capital of windsurf) but any part of DR (except inland) is great for sailing.
Its veery cheap also and most resorts have sailing watersports included in the vacation package!!
wave im glad you have visit us several times, i agree cabarete is laser mostly, but not far from there its samana and to be more precise --las terrenas-- there youll find more sunfish fleets
The fleet in santo domingo you are referring its the one in boca chica (club nautico).