I have been to Jamaica four times in the last four years. Not windsurfing but going to Sandals resorts. They have really old HiFly poly boards and small sails, but I haven't used them. I go to relax, scuba dive, kayak, sail Hobie cats, golf, eat and drink (all inclusive at Sandals).
During the four visits, one in July and three in November, all at different locations on the island, there seems to be trade winds from the east, averaging 10-20 knots most days. I have usually been on the north side of the island between Montego Bay and Ocho Rios, so the wind is always side shore. Always nice swells outside the reef and very flat water inside.
There is a barrier reef that surrounds the entire island, usually about 200 meters off shore. There are plenty of cuts through the reef, so getting outside is possible. There seems to be a lot of places to launch, but security could be a concern.
I have no idea about rental gear. I have never seen anyone windsurfing accept at the Sandals resorts, and few take advantage of the opportunity. Basically, it's beginner gear for teaching.
The island has possibilites, but I can't be of much help.
Formula 160; iSonic 111; HiFly Move 105; Tiga 263; '85 Mistral Superlight.
Maui Sails TR 11.0; 9.2; 8.4; 7.6; 6.6; Maui Sails Switch 6.0; 5.2; Maui Sails Global 4.5; 4.0.
Last edited by Ken; 4th December 2009 at 12:32 AM.