Middle Keys to Key West

I landed on the Man o’ War covered Smathers Beach on the south end of Key West at around eleven in the morning. I jumped out of my kayak in front of dozens of tourists trying to tan their wintery white skin. My face was coated with zinc oxide, my eyes sunken in from lack of sleep, my clothes wet and smelly. I sat on the beach in the warm sand for a moment reflecting on what I had just done. I had paddled a kayak the same distance it would be to paddle to The Bahamas. The absurd goal, an unfathomable distance, didn’t seem so crazy anymore. The only difference, no bugs to fend off, no unpredictable currents, just open water and solitude.

The adventure began at two in the afternoon the day before. I set off from my parents’ home on Duck Key, Florida. I was fairly new to sea kayaking and I felt my paddling technique evolve from theory to practice over the first ten miles. I eventually made it to a long stretch of open water, jutting out from the harbor into thirty foot deep water, over a mile from land in any direction. Boats sped closer to land. Out in this deep water I was joined by sea turtles and fish swimming through the clear blue water above a sandy bottom. The swell picked up and the currents from the channel quickly made me sea sick to the point of nausea. The rocking of the confused seas on my twenty one inch beam drove me to frustration and eventual vomiting into the sea. I soon arrived at the opposing shore where the water flattened and I could relax.

I hugged land until dusk when I once again left the comfort of the shore to paddle out into open water along The Seven Mile Bridge. As the sun was setting a large fishing boat headed into dock turned around and gunned it out to me. Several fishermen, with tanned skin from their life on the ocean probably saw a white skin kayaker like me as an eventual rescue. They drove up next to my boat and shouted “Are you alright?!” almost certainly wondering what the hell a kayaker would be doing about to cross a seven mile stretch of water in the dark. I waved back and confirmed their suspicion that I was simply mad or stupid and did fully intend to do what I was about to do. I knew what I was getting myself into, and I was okay with that.

The previous night a friend of my dad’s had encouraged me to refrain from being the first person to paddle a kayak from Key West to The Bahamas. The weather appeared to inhibit such a trip anyways. I told him of another goal, a much safer, but more physically challenging trip from the middle keys to Key West. He doubted that journey too and seemed to expect to see my parents driving off the island to come pick me up early. I listened to his suggestion and the next morning quickly packed up my boat for the trip that would normally take a paddler several days.

But the adventure of riding close to land was proving to be more challenging than I expected because of the unpredictable currents. Within half an hour of paddling away from land, a five foot shark collided with the bow of my boat, likely unintentionally while trying to grab dinner. The experience was enough to solidify my excitement and the freedom of having only wildlife as my companions for the night. The moon was already in the sky by the time the sun set and lit the way for my paddling with no need for a headlamp. I could see green-brown murky bottom covered in sea grass and meandering shrimp and fish beneath me, eyes lit by the moon above. Bioluminescent plankton splashed off my bow and swirled with every paddle stroke, turning the water a beautiful glowing blue. I would paddle across schools of flying fish and with the silence of a sea kayak, startle them into leaping fits, not knowing which way the disturbance came from. Each time I would drop my paddle and grab the sides of my head, having the foot long fish collide with my hull, my torso, and my arms for a few moments before they all dispersed and returned to their marine habitat. The loud clunk of their foreheads on the fiberglass of my boat made me cringe for their little brains but eventually I came to hate these little gliders as the routine of collisions continued far too long into the night.

Exhausted from multiple bouts of vomiting in the confused chop, I shoved my boat into some mangroves in early morning and pulled down into my hull to close my eyes. I awoke after the deepest nap of my life to hands that were coated in a black film of sandflies, a problem I envied that I would not have to deal with in open water. My blood was being sucked from my flesh while I slept. I moved on after a few minutes of slurred curse words and was back out on the water with the moon directly in front of me. Soon it set below the horizon and left me in the deep lonely darkness. I left my headlamp off, following only the outline of the mangroves contrasting with the water and the lights of Key West nightlife guiding my way.

When the sun rose to just below the horizon I felt an irresistible smirk stretch across my face. This was my destination, not Key West. The challenge was to make it through that darkness and I had done that. The paddling became easy with the warmth of the sun. I coated my face again with zinc oxide and with a light breakfast, soon paddled into the hustle of Key West Harbour. Boats flew by me heading out for their daily fishing runs. Sailboats were headed west to the Marquesas and on to the Dry Tortugas. I was done though. My adventure had spanned through the night in total solitude and darkness.

This goal was not my own. Rather it was a confirmation that another one, a much more challenging adventure was feasible. Besides navigation issues, it is possible to paddle a kayak from Florida to The Bahamas. That will be the first step on hopefully an adventure of epic proportions along the island chain of the West Indies.

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Grayson Cobb

Grayson Cobb

I am a long distance backpacker, triathlete, adventurer, climber, kayaker, and lowly medical student currently living in Norfolk, VA attending Eastern Virginia Medical School and getting out for adventures on weekends.
Grayson Cobb

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2 thoughts on “Middle Keys to Key West”

  1. cool. did you have a gps. what was your average speed? how much sleep total did you get and how long did you rest – or was it near continuous paddling except for the nap?

    1. It was around 3 knots average speed. It was continuous paddling except for the nap. Pretty grueling. I just think about Andrew McAuley’s 35 hours across Bass Strait and cringe-pretty hardcore stuff. I think what beat me so badly was just the night paddling. While I enjoyed the beauty of it, it did get pretty lonely out there.

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