Boat days here are cancelled less often than on exposed coasts, because the route north runs behind the barrier islands rather than out in the Gulf. But three things will stop a trip.
Lightning. Summer afternoon storms on this coast build quickly and carry serious electrical activity. Operators will delay or cancel, and they are right to. If you are booking in June through September, book the morning departure and keep the afternoon free.
Sustained wind. A hard north or northwest wind pushes a chop across the open stretches of the sound and makes landings on exposed beaches unpleasant or impossible. This is a winter problem more than a summer one.
Fog, occasionally. Calm humid mornings in winter can produce fog thick enough to delay departures by an hour or two.
Take with you: sun protection far beyond what you would use at home, because the water reflects and there is no shade on most decks; a hat that will not blow off; a light windproof layer, since thirty knots of apparent wind is cold even in Florida; polarised sunglasses; motion sickness tablets taken before you board rather than after you feel unwell; and cash, because small island establishments do not all take cards reliably.
Leave behind: anything you would mind losing over the side, and any expectation that the boat will wait. On a bridgeless island the return departure is the whole schedule.