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Solo to Key West Pirate Looks at 60

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*I am now 70, written 10 years ago..thanks!

Tampa to Key West….Solo Sail

Being a pirate looking at 60,, I decided to see if solo sailing would increase my self confidence or would  fuel my self doubt .

The day was sunny and bright when I left Davis Islands and headed my Freedom 40 south to Key West.   Tampa Bay slowly disappeared behind my wake caused by motor sailing in the light winds.  Fuel tank full, autopilot performing, bimini protecting my from the sun, Sirius radio playing 60’s and Jimmy Buffett, what a start for a wonderful adventure.  We all know that despite the best weather/wind forecasts, once we are offshore the conditions can be challenging.

My Freedom 40 has all the lines running back to the cockpit where an electrical winch makes sail handling manageable..  Once the sails are up on the ketch/cat , freestanding carbon fiber  masts flex  and the sailing is wonderful.  No releasing of jib sheets and the selftacking main and mizzen are a delight.

After sunset the full moon illuminated the water and I settled in for a peaceful night.  Around midnight the winds increased to 20  knots and after  some northeast orientation, switched to easterly with a slight southern aspect.  The seas increased from the east and started hitting the port side, throwing water up over the rail.  So much for a peaceful easy night motorsail.

I had left the full main up and with the motor running a low rpms was able to maintain my southernly course .  The real challenge to solo sailing is maintaining a lookout for traffic from freighters,shrimpers, other cruising sail and power vessels.  I had bought an egg timer and  had planned to set it for 20 to 30 minute alarms.  Actually, I would rest my eyes and was able to awake shortly to make observations.  No shrimpers, freighters, cruise ships , other boats were seen that night.  The lack of sleep does take a physical and mental toll.

My safety plan also  involved jacklines running fore and aft,  a good sturdy harness with two tethers so that I would never be unclipped,  a Spot satellite gps messenger, VHF radio, ham radio, two large GPS transmitters, and a liferaft at ready.  An inflatable pfd allowed me better movement than the larger offshore jackets. My sailboat does have three independent bilge pumps and the diesel has been running well.  Plenty of water, fuel and food.  Flares, both handheld and parachute, supplement my emergency  equipment.

In the middle of the night,the large waves headed   west like a herd of buffaloes.  Some pass quickly and quietly, while  others collided  with the boat and heaved  me over .  A quick check below found  all my belongings that were nicely stored are now on the  sole.  I make a mental note to be more shipshape for my return from Key West….It was like someone taking your home and tilting it to shake everything possible from it’s assigned  place.

My chartplotter gave me confidence in both my progress in the gulf as well as heading down the Key West  channel to my final destination, the Key West city marina in the bight area.  I realized I wasn’t as strong as I was when I was younger, and my balance also wasn’t as sure as it had been on previous night sails. Self doubt sets in and I asked myself what the heck am I doing out here.    I really did not want to go up on the foredeck , in the middle of the night, to reef the sail or check on the secured equipment.  I did have to go forward in the channel and dump the large main sail, get it tied to the boom, and continue on a safe course.  With the strong winds and the sail not cooperating,  it took more effort and was done slowly and with difficulty.

I arrived in Key West to my slip around 4am, a total of 42 hours underway.  I would prefer to have crew so you can really get some good sleep and have some companionship.  Another option is  breaking up the trip into more manageable segments, possibly a stop in Marco, or even smaller segments.  Take the time and enjoy the journey more.   I did have by tow insurance if needed but all was ok .  A radar system or AIS ship identification are both on my future purchase list.

As most cruisers realize, once at our destinations,  our sense of achievement is heightened and  the memory of the long , sometimes wet and stormy nights , is minimized.   Discomfort  and the constant attention to the aspects of sailing both make solo sailing challenging.

I plan on leaving Key West after fantasy fest and shortening  the sail by stopping in Marco Island, or at least taking a rest interval in Longboat Key.  I do enjoy my independence and solo sailing reinforces my concept of self dependency and enhances my self confidence.

It is a great feeling of being on a seaworthy boat , solo sailing and just being in the element.  It is a private time and one of great appreciation of ourselves and the beauty of the sea.  It is not to be taken lightly, as even well crewed boats can be extremely challenged .  Try a long solo daysail in good weather and see if you are comfortable alone on your vessel.  I do welcome additional crew at times but find the solo sail very energizing and a very personal, spiritual engagement with nature.



Capt.  Herman Bips III has been sailing the  southwest coast of Florida and Key West for many years.  He holds a 100 ton Coast Guard  captain’s license and does charters  and pleasure sails on his Freedom 40  cat/ketch , home port is Davis Islands , Tampa, Florida.    Other sails have included Cuba, when allowed, and the annual St. Petersburg, Isla Mujeres Race.  Feel free to contact him at





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