Key West & The Return to Reality Regatta

Racing from Naples Florida to Key West and back


Tired…in the Best Way 

After a personally EPIC dive, I spent the some time hanging at the boat, enjoying the skippers hospitality.

The boat deserves a comment.  Its the best equipped boat I’ve sailed, since  2005  with Burley.  It has all the required equipment for a Cat. 2 offshore race…. And, everything is  in good shape and ready to be deployed.  The lines are good, the sails are good.  Their was a jackline and clips positioned for rough weather.  It’s hard to find anything to complain about.   Well OK…. The propane tank was out, so no coffee or hot meals but that didn’t bother anybody.  The cabin is light with long windows and light colors.  The wood, is Cherry Yew, a species popular in Europe and not easy to find.  The cabins and salon were just the right size and Jay had added grab rails and leeboards to make it safer and more comfortable during an offshore passage.

I especially liked his playlist.  It was an eclectic mix of old and new.  All the songs we grew up with and a bunch from the 30s 40s and 50s that neither of us were alive for the first performance.  Seems we were both the children of music loving families with an early connection to vinyl.

So I spent the early afternoon recovering from the dive and listening to, The Beatles, Billy Holiday, Cab Calloway and Gershwin.  I did a quick edit of the mornings footage.  It was amazing!  If you would have asked me a week ago, if I would be interested in a serious penetration dive at 100 feet I would have said, “No Way”.  When I booked the dive, we didn’t talk about it.  He asked me what my certification was and when I said, “advanced”, he just nodded.  It wasn’t until we were away from the dock and the briefing started that I learned the particulars.  And…. Here it was, I was not only going inside the hull but transversing it and entering spaces with no visible exit.  Wow!  I’m going to be reliving this one for awhile.

When Jay showed up we went back to the Commodore to try their famous burger that wasn’t available on the dinner menu.  It was hot but that didn’t stop the continuous parade of beauties and tourists strolling the boardwalk in front of us.

That evening was the award ceremony at Dante’s.  There were several fleets and two starts with small fleets.  Since they were giving awards to the top three, just about everybody got time on the podium. About half way through I was feeling like somebodies uncle at Graduation.  Playmobil received a handsome framed burgee of the Conch Republic and we trooped up front for the photo shoot.

Everybody got a Trophy

That night I was planning to take in the songwriter/singer fest but I’d had enough excitement and opted to go back to the boat and sleep.


Return to Reality Regatta


There were only 5 or maybe 6 boats in the start but our fleet was intact.  Fancy Free, Southern Cross and Playmobil loitered around the mark trying to gauge the current and figure the best place to be at the start.  Nothing too exciting, Don, Bob and I were in position and the winds were an easy 7 – 10.  At one minute we were making our way to the line on starboard with Fancy Free behind us.  Southern Cross was making for the line on port tack and it was obvious that they wouldn’t make it in time to cross before we got there.  Jay hollered, “starboard” and Bob repeated it just for good measure.  From the actions of the Crew on Southern Cross it was clear that they heard us but their Skipper held his course and Jay was forced off his course.  We were clearly fouled and Jay didn’t hesitate protesting.


I was right!  The “Big Boxy Skipper” was a bully.  He drove his boat right at us!  We had to turn or T-bone him.  He had nothing to gain by hammering us at the start.   He was bigger, faster and pointed better.  What a jack ass!  Jay put up the red flag and we continued the race.

As we pulled away from Key West a colorful little bird joined the boat and stayed with us for several hours.  He went below a few times but never stayed long.  Occasionally he would fly off the lee side and pace us for a few minutes and then return.  I took half a dozen bad photos and only got one of the bird.  We also had a small pod of dolphin hang for awhile.  Good times!

Light winds on the nose kept us pointing through the day and that evening was light and variable.  The wind was swinging on a 90 degree arc making it a chore to keep good VMG.  At dawn we were treated to a beautiful sunrise that no cell phone could capture.

Marco Island (I Think)
The winds were too light for the genoa so Jay decided to set the spinnaker and fly it like an asymmetrical.  I had a brief hero, moment when Jay lost the spin halyard and I had to go up the mast a few feet and retrieve it.  It was a frustrating situation, the halyard was swinging just within reach, then it would get wrapped around something and hang beyond my grasp.  Eventually it unwrapped and I was able to grab and bring it down.   Spinnakers have always intimidated me  but after working the “pit” position with Nuzzo and todays experience.  I’m think, I’m beginning to get it, I look forward to the next time and hope we can tack a few times so I see how its done.  Like a lot of things, once you’ve done it a few times it starts making sense.


So… We were sailing along just fine, our competition was out of sight but there were sails behind us for perspective.  It was all good.  Bob and I were high in the cockpit on the windward side, when… BANG… Sounding like a .30.30 the windward chainplate exploded.  My first thought was the carbon mast had failed and we’d lost the rig but when I looked up I could see the mast was intact but swinging wildly.  Jay and the crew were great, almost instantly, the main was eased and we started to get the spinnaker down.  I was having a hard time pulling it in and thought the halyard was still locked or maybe something else was preventing it from coming down but when another hand, got to pulling, it came down fast.  Some of the spinnaker hit the water but we got it aboard.  Jay’s first order was to chill for a second, then he called for a couple of life preservers, and then, we took down the main.   Next we used the spinnaker halyard to begin to brace the mast.  While were rigging the spin halyard I could see the mast doing sine waves and wondered how much it could flex before failing.  Jay had me go below and bring up some Spectra. We tied a bowline on a turn buckle and ran it through a spinnaker snatch block and  back to a winch.  Realizing that only the lowers were braced we repeated it with another turnbuckle and tensioned the uppers.  Now the mast was looking good.   With disaster avoided we started the motor and headed for Naples.

We had been debating weather or not to leave the boat in Naples and retrieve it later or stop at the Yacht Club, file our protest and continue on to Charlotte Harbor. Now, it wasn’t an option,  Jay had to get the boat north or  deal with it stuck in a remote slip for possibly weeks.  The protest was a moot point since we didn’t finish so we made Naples and dropped Bob and Don at the first open dock.   They shuttled the cars back and Jay and I brought the boat home.

Other than a broken rig, it was a nice ride.  I got to see the IWC up past Fort Myers beach and the West side of Pine Island.  We were watching some weather to the North West and Don called to tell us there were small craft warnings and water spouts but we were below the worst of it and never even needed the foul weather gear I brought up.  Getting into Ponce De Leon after dark was a trick but Jay had us at the dock well before 11:00 and I was in bed by Midnight.


Just missed the storm
IMG_5689The next day we met at the boat and put it away for the season.  Thanks for the great experience Jay!

Author: JoeO

Powered Paraglider pilot since 2005

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