On the west side of Windley Key is Whale Harbor, which separates Windley Key from Upper Matecumbe Key.
Historically, Whale Harbor only contained Wilson Key, and had been called Wilson Creek. It was a good anchorage and passage to the Bay side for larger visiting boats, until the railroad dike was built. We imagine, in its heyday (before the railroad), boaters must have joked the passage was so roomy you could park a whale in there.
Most of the dike blocking Whale Harbor is still in place, now as Keys highway dike jetties protruding into Whale Harbor from both sides.
The water blocking dikes need to be removed. Only fill that is in the water flow shadow of Wilson Key needs to remain.
The dikes to remove, denoted with red X above, are: the entire jetty from Upper Matecumbe (upper left in this figure); and most of the jetty from Windley Key (bottom of figure).
The dike (jetty) from Upper Matecumbe to the bridge should be removed, and a bridge should be built all the way from Upper Matecumbe to the area denoted FILL, allowing water to flow under the entire bridge without a dike.
The jetty from Windley Key to the area denoted FILL should be removed with the possible exception of leaving the FILL area in place, since it is in the flow shadow of Wilson Key. A bridge should be constructed from Windley Key to the FILL, allowing water to flow under the bridge without a dike.
An alternative, to having two bridges meeting at the FILL, could be to have a single bridge from Windley Key to Upper Matecumbe. In that case, supports for the bridge could be built on the FILL.
The bridge or bridges do not need to be very wide, because a separate bridge for most traffic will eventually be built, possibly in a different location, between Upper Matecumbe and Windley Key. That bridge will be longer and will be concrete box girder as described in the bridge construction page of this report. The route of that bridge is not yet decided. Two possible routes are over sand bars on the Atlantic side, or as an overpass over the dike highway. If the latter case, it would be well above Whale Harbor, not need jetties, and no other bridges would be needed at Whale Harbor — the area under the overpass could be used for parking, docks, etc.
The portions of dikes to be removed (denoted with red X in the figure above) need to allow storm ebb current to flow through. Docks for boats could be constructed in both of these areas, if the docks are designed to allow storm ebb current through. For example, the docks could be oriented parallel to water flow, connected with cat walks that are removable during storm evacuations (e.g., retractable, swing-arm, etc.).
A few years after the above aerial photographs, Hurricane Donna came through. It had much less storm surge than the 1935 hurricane. The storm surge of Hurricane Donna took 4 days to drain back out to the Ocean after the storm — would have taken a fraction of that time without the dikes and viaducts.
The following photograph shows the Windley Key dike jetty in Whale Harbor blocking the ebb-current (return flow) of the storm surge of Hurricane Donna.