I did the trip in May this year from Tampa Bay through Lake Okeechobee to Florida's East coast but than north to the Chesapeake.
The draft on my IP 37 is 4'6" and my mast height is 49'5" above water. We saw 6 1/2' of water at any point and just made the infamous railroad bridge (ooficial clearance 48') by just touching the very tip of the VHF antenna on my mast.
I called the corps of engineers the day I entered the Caloosahatchee River in Ft.Myers and they were very friendly and gave me exact info about the official water level in the lake and what that means to both the bridge clearance and minimum depth to expect within the lake.
You will motor most the time from Ft. Myers to the Lake and from the lake to Stuart but it is a nice voyage through central Florida.
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Island Packet 37 (hull53)