Welcome to South Florida ! We are locals and will be riding in the Keys, specifically in Islamorada, at Whale Harbor 10/15 - 10/18 if you make it down that way, it is the best area in South Florida to ride. Also will be riding before and after at Matheson Hammock in South Miami and 87th Street on the ocean side in Surfside the rest of October when it's windy. We also take the boat out to Stiltsville off of Key Biscayne which is an amazing flat water spot.
Hope we all get a lot of windy days and that that you have a great time while you're here.
If you need any local info shoot me an email:
getnair@aol.com
See you out there,
Paul