did a SW FL week last April, rode the causeway a few times and Boca Grande once.
PI sound has potential but it also has mangroves, limited access and
and I've been hearing about the vibrio infections lately, not sure if it's in that neighborhood of FL but you would not want to get cut to ribbons AND deathly ill with fever.
The locals ride:
The causeway islands
Ft. Meyers beach (nice beach once you are on the sand, otherwise hell-hole esp. traffic and appologies to locals, but ft myers beach is terrible for tourists)
downwinders e.g. north end captiva (or around mucky duck for most i guess) to blind pass, blind pass to whatever sanibel beach or vice versa depending on wind direction.
If brave and able to avoid oyster death, you could rent a little skiff near the causeway and find your spot, but the causeway pull-offs get you to oyster-free water, wind and away from the strong currents draining the sound to the south.
Don't get swept under a bridge or go too close to the mangroves/snakes/oysters/gators(?). Flats around them can be extensive.
The causeway was ok, but boy was it worth it to drive up to Boca Grande for a session.
The gulf from Captiva north is more "gulfy" and beautiful than Ft Myers or Sanibel, which are near the river and PI sound and more turbid, though warmer.
Charlotte harbour behind gasparilla would be incredibly awesome for a sesh, but I only rode outside:
Sure some folks on Gasparilla might look at ya funny but there are some funny looking ones there to be sure. mostly americans and I saw a few russians.
If as I suspect, you have been to matunuck as well as newport, Providence as well as watch hill, etc, you can take it all in stride I'm sure.
But if you feel compelled to spend $40 on a salad and a glass of wine, there is really no need to do it at the pink.
Captiva has the best vibe in a way and more eurotrash in the mix, versus the cornfed predominance of PI.
Not that PI couldn't be great if you knew its secrets and had a boat. There are some marinas/docks, but not many.
Pine island seems mostly dedicated to private tranquility largely enjoyed by Michiganders and not all the restaurants are good either. Drove around there one afternoon/evening, didn't find anything great. With the right connections/intros though it is probably awesome and very laid back.
Have a hunch the bokeelia/north end has more to offer, did not make it there.
I flew in, knew no one, stayed in northern cape coral and had to drive to all these islands.
Some of the tolls were less than $6.00
sorry that was not a joke.
Another great possibility lies across the sound, between Boca Grande and Captiva, the undeveloped Cayo Costa, a state park. Appears to have miles of beach and some buttery lagoons, again maybe with a risk of shallow oysters, not sure about that. You can get a ferry to Cayo Costa or hire a water taxi $$$. Regrettably we didn't make it over there. And I don;t know the official stance if any on kiters there.
Hope you have fun, bring a big kite.
And a skiff if you can.
All these spots have pluses and minuses, but there is definitely some awesome seafood on the beach after.
Cobia or triple tail at the lighthouse, sanibel. awesome.
Whatever at the mucky duck. also awesome, with a sunset.
Faux cocktails though.
lee side of causeway:
Sorry didn't have more specific info on Pine island, hope this is somewhat useful.
If I went again I would stay on Sanibel or Captiva, or if a high roller, I'd do Boca Grande with a boat.