A Tale of Two Halyards

I bought Gypsy Wind in the fall of 2023, full of dreams and optimism.  I had the boat.  I had the river.  I had the wind.  What I didn't have was a halyard that could actually raise a sail.

I had several months of planning until she came home and then exactly 7 days until launch.  It was a whirl wind of excitement, prep, launch day and a week later we stepped the mast.  That’s always fun with a new boat because you have to figure everything out and I swear I learn nothing, it’s the same chaos every year.  I hadn't thought to inspect the wire cables.  Besides, what would I look for?  I was oblivious to any potential problems. I just assumed it was fine.  Spoiler: it wasn't.

My First Sail

I was stoked for my first sail.  I figured out which line was the jib halyard, pull on it but it wouldn't go up more than 6 or 7 feet. I scratched my head and heaved on the line, lifting my feet up off the deck and swinging around for extra weight. As if that would fix anything.  No luck.  I jiggered around a little bit, but I really had no idea where to start trouble shooting.  My heart sank down to the soles of my feet.  I couldn’t believe what was not happening.  You’re supposed to pull and the thing comes out.  It’s not that complicated. I’ve done it before, just not on this boat.  I honestly had no idea what was going on. I reached out to my trusty tribe.  They figured out the problem was somewhere at the top, but it would remain a mystery for a while yet.   We met up at the wharf, set up the gin pole with Duffy strapped in the Bosun's chair, attached safety lines and lifted her up to the top. 

Some Friends Bring Snack and Wine Duffy Brings the Boson's Chair.

Look at what she found…

Looks like a Ramen noodle

Looks like on of my 1980's perm.

Two Halyards - The Tale

Not only was the jib halyard curled - like how I wish my poker straight hair would be - but so was the main. They looked like someone took a butter knife and tried to make curly ribbons.  Both of them.  Two halyards, zero sails.

We managed to hoist my storm jib, a tiny scrap of sail, not much bigger than me, that technically counts as sailing if you squint.  But the wind never showed up to play along. Honestly?  I wasn't ready to raise the main, but I was still disappointed. 

I literally bought a sailboat that I couldn’t sail.  I couldn’t believe my luck.

At the end of the sailing season, we were sitting around talking about our adventures and a very kind fellow sailor who has helped me out more than once already, showed up with a complete rope jib halyard that fit perfectly.  So, we swapped out the old halyard and replaced with the new to me halyard.

Who Needs The Main Sail?

I was so ready for 2025, I wasn't worried about not having a working mainsail. I knew I could have just as much fun with the jib. In late 2025 that same friend found a halyard from one of his previous boats for my main.  Guess what, it works.  It doesn’t fit perfectly but pretty darn close.

I Couldn't Raise My Sails That Day 

But I learned something about my boat that I should have known from when I purchased her.  And now?  I inspect those halyards twice maybe three times.  Yes, my tribe laughs at me.  I don’t care, I’ve seen things.  I did unintentionally buy a boat that I couldn’t sail but it led me to discovering an amazing community that steps up to help others lend a hand, knowledge or spare parts freely.  As a newbie boat owner / sailor what better ending can this story have, making great friends along the way and now I have working halyards.  I can’t wait for the 2026 sailing season to begin.