How We Learn

Debbie Leisure learns to sail her boat single-handed.

Debbie Leisure I learned to sail with my husband.

We took lessons together, chartered boats together, bought our first boat together, and then our next boat—the one in which to go cruising.

I learned my “things” and he learned his.  We tried to cross-train, and sometimes it worked.

It wasn’t until he died suddenly, a couple years into our cruise to the Caribbean, that I suddenly realized the many things I didn’t know how to do.

I had never changed the oil or bled the fuel lines without supervision.Several very important things.

I had never picked up a mooring single-handed, never sailed alone, never changed the oil or bled the fuel lines without supervision, and very importantly, I had never, no never, docked the boat.

I made the decision to keep the boat and single-hand, but I have to admit, did not take any real steps to make that a reality.

I was very good at sitting on the boat, attached to a mooring, in Carriacou, Grenada.I was very good at sitting on the boat, attached to a mooring, in Carriacou, Grenada.

I was okay at sailing with friends on board to crew for me.

But most of the skills that I was not sure that I had and needed, I had to be FORCED to learn.

A step

The first time I went sailing alone, I was supposed to be in the company of two or three other boats.

Sunset at Union Island in the GrenadinesI left earlier on the sail to Union Island, as I was the slowest boat and they would be right behind me. However, they were all delayed in their departure, and I was anchored for hours before anyone else arrived.

I had completed my first sail, with no major problems; I had anchored alone with no advice or assistance.

I would not have planned it that way, but it turned out well and gave me confidence.

Another step

Upon leaving the dock one day after taking on water, a friend came on board to assist me in picking up the mooring again.

However, after getting underway, he informed that I was never going to learn to pick up the mooring alone if everyone kept helping me. So being the good friend that he was, he was going “to do nothing” while I did it alone.  Of course, he was right. He offered a little advice and sat back to watch.

I picked up the mooring without his assistance, gained confidence and never asked anyone again to help me.

Again, I was “forced” into learning a skill and attempting a maneuver I was uncomfortable with, and came away feeling much better about my abilities.

And another step

I firmly believed that I could not dock the boat, but Nolan COULD walk on waterIt was about this same time, that Nolan, from the haul-out yard, came out one day in his dinghy to advise me that he was ready to install my new electric windlass if I would just move the boat to the dock.

As he started to motor away, I called him back and explained to him that I did not dock the boat alone, had never docked the boat alone, and he must come onboard to assist me.

Even with assistance, I was not confident in my ability to dock the boat, as I had never docked the boat when my husband was alive and had only docked it a few times since then with experienced people onboard telling me exactly what to do.

However, Nolan had other ideas.  He patiently explained that he was sure that I could dock the boat. He said he would go wait on the dock for me and if I needed assistance, he would “walk on water” to come help me. Since I have great faith in Nolan’s abilities (I firmly believed that I could not dock the boat, but Nolan COULD walk on water), I agreed to do it his way.

I approached the dock with trepidation, but there stood Nolan along with three others from the haul-out yard to help me. Of course, just as Nolan had said, I docked with no problems.

Again, I was forced to learn and acknowledge my abilities that I didn’t even know that I had.

I seem to learn best the hard wayIt seems most of my learning has been that way.

Forced to do what has to be done, when it must be done.  I seem to learn best the hard way.

But with the help of many friends, sailors, workers and strangers, I continue to learn.

Heading North

Heading NorthI left Carriacou, Grenada, in January 2007, having made the decision that it was time for Illusions and I to return to the States.

I had a wonderful buddy boat to travel with, a boat as slow as I was. It took me six months to sail from Carriacou to Puerto Rico.  Some of the stops were just for fun; many were for working on the boat. Either working on things myself, or finding professionals along the way.

 I had engine problems, blew out a sail, broke a dinghy davit, and on my one overnight sail the autopilot failed. I had engine problems, blew out a sail, broke a dinghy davit, and on my one overnight sail the autopilot failed.

All these things happened under way and had to be dealt with alone until I could reach the next island and assistance.

I learned patience if nothing else.

I stayed in Puerto Rico a year, then continued on to the U.S. I had a friend that crewed for me for the Puerto Rico to Charleston, SC part of the trip. I did my longest passages to date, only making about four stops between Old San Juan and Charleston.

Next Steps

I plan this winter to sail to the Bahamas for the winter.

I try not to think about the things I’ll be forced to learn along the way, but the cruising lifestyle thus far has made it all worthwhile.

About Debbie

Illusions - my 29' Island Packet - in Culebra Debbie Leisure sails her 29′ Island Packet, Illusions single-handed. Originally from Missouri, she sailed the Eastern Caribbean for five years. Recently, Oriental NC has been her home base, but she plans to sail to the Bahamas this winter.

Carriacou holds a special place in Debbie’s heart. She flew back this August for the annual Carriacou Regatta, saw old friends and had a great time racing.

Debbie helped out at last year’s Women and Cruising Seminar at the Annapolis Boat Show. She shared her experience when women asked about what you need to know in case something happens to your husband/partner. Debbie, along with several other Women and Cruising contributors, hopes to attend this year as well!

Related articles (on this website)

How did you learn your sailing/cruising skills?
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1 comment to Debbie Leisure learns to sail her boat single-handed.

  • pamela barclay

    very inspiring to hear your tale of taking on singlehanded sailing. I have a 32′nauticat in scotland and a partner who is not so interested in sailing – i do day trips out singlehanded but long to gain the confidence to go further afield and overnight alone. best wishes pamela

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