Rule #1 : never leave home without your kite gear...especially if you'll be in FL for a week!!!
The closets I've ridden to Pine Island is Sanibel, which can be great.
I've been out to Pine Island a few times (Matalacha, Bookelia) and it looks like lots of possibilities there.
If you can get a boat over to Captiva or Punta Blanca Island you can probably hit some incredible shallow water, flat water riding in every wind direction.
You may not encounter a lot of other kiters out there, it's pretty remote from the popular spots, but it could be epic. depending on where you are on Pine Island, Sanibel could be a good hike.
enjoy your trip...Pine Island is a cool place!
PS...is that "Southie" as in S. Boston?
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