Toby, the two spots are quite close together, less than 7 miles apart more or less east to west. There are wind meter stations in the area of each but they have their wind artifacts. I would say to call each concession to get a read on actual riding conditions today. I will PM their phone numbers to you.
Here is the NWS forecast, the best one I have found for the area.
Today: East southeast winds 11 to 16 knots. Seas 2 to 3 feet. Dominant period 4 seconds. Intracoastal waters a moderate chop.
Tonight: East southeast winds 13 to 18 knots. Seas 2 to 4 feet with occasional seas to 5 feet. Dominant period 4 seconds. Intracoastal waters choppy in exposed areas.
Friday: Southeast winds 9 to 14 knots. Seas 2 to 3 feet. Dominant period 5 seconds. Intracoastal waters a moderate chop. A slight chance of showers. http://forecast.weather.gov/MapClick.ph ... mx=1&zmy=1
wind looks not that strong...so if Crandon is stronger, better to go there.
Any actual wind graph for both locations ?