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The wind was out of the east and I knew that the east side of the island would be difficult going into the wind and current so I chose to used that fact to make my decision to travel clockwise around the island.
I passed under the Cow Key Bridge and out towards open water. I was surprised by the lack of trash and derelict vessels, they really cleaned up the area since I was on the water there years ago.
Once in open water near the airport and beaches I had a quartering tail wind of 10-15 mph that kicked up some waves and I had to be careful about how I traveled to avoid taking in water. I didn't enjoy it but it was much better than quartering into the wind and waves. Be careful not to pass to closely to the seawalls and piers if you have wave action as they tend to bounce back and create some sloppy water.
I passed by the county and city beaches to the southernmost point and then Fort Taylor. Fort Taylor has the best beach in Key West and has some large rock piles out front. I took advantage of them to duck in for a drink and to bail out some water that I took in.
As I rounded the fort (which you really can't see much of from a kayak unless your offshore a bit) the cruise ship docks came into view. No ships in this day and I ducked into the shelter of one of the marinas to eat a sandwich and rest.
After passing the USCG Station I had the choice of doing a bigger circle around Flemming Key (?) or cutting under the bridge along the Navy property. I chose to try the bridge and fought a 4 mph current to get through.
I crossed the anchorage and rounded the military campground and was back at Niles in under four hours. Total trip was about 12.6 miles.
I won't try this trip again unless the tides are in my favor and the wind is down. Last week I did a 22 mile trip from Marathon up around Duck Key and back that was much easier than this. This one was a workout as I was always fighting some act of nature. I don't regret it as any trip that doesn't involve injury or loss of equipment is better than 4 hours in a dealers waiting room.