Adam,
The riding spots in the keys are as follows:
Whale Harbor Marina, Upper Matecumbe
Anne’s Beach, Lower Matecumbe
Long Key State Park, Long Key
Cury Hammock
Coco Plum, Marathon
Sombrero Beach, Marathon
Bahia Honda
Smathers Beach, Key West
Bahia Honda and Smathers Beach are the only 2 true beaches with ample sand. The rest are abit tight. All the above launches face S-SE. East winds are the best as they are side to side on winds. When a NW-N winds hits they are usually very strong and not uncommon to peak at 45 mph.. The launches on the north side are few at best. For this we go to a select few spots for the best riding and most spots a boat is needed. If you are in the keys and need people to ride with or just have questions about the area, either ask here or call The Otherside Boardsports at (305)853-9728.
Stay safe and have fun!
Noel
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