Highs and Lows of Sailing a Pocket Cruiser with my Family

Posted on July 9, 2013 by


You know that feeling when you are searching on Craigslist or Ebay and you are tempted to buy something really expensive and indulgent just because it looks like a lot of fun?  Well, we did that a year ago when we impulsively bought a sailboat.

I was bored one night and I hopped on Craigslist to see if there were any sailboats for sale.  I quickly spied the listing for a 1985 Sanibel 17, a trailerable pocket cruiser with steady production over the last thirty years and a loyal following.

She will not win any races with her beamy hips or catch one’s eye with her protruding cabin.  But I was able to look past the aesthetics and see an opportunity to take my family sailing.  Trailerable so that we could sail her anywhere.  Slow and stable to keep her upright and safe.  Comfortable cabin for children to play in underway. A Bimini shade to protect my wife’s fair skin.

We bought the boat a couple weeks before Link was born and I wasn’t sure if we were going to get out that season.  That was why all I could do was smile as we tacked under the Tappan Zee Bridge a month later. The boat heeled over as the wind filled her sails and she settled into a nice motion through the water.  Looking into the cabin I saw my wife reading stories to my daughter and my son Link sleeping in the Moses basket.

It wasn’t THAT impulsive

The truth is that I have dreamed about taking my family cruising for my entire life.  Even before I had a wife or children I dreamed that one day I would sail off to the far corners of the world with my own family.  This may seem like a strange or abnormal dream but it is merely me trying to relive my own childhood.  I sailed halfway around the world with my mom and stepdad from ages 8-12 and to say it left a positive impression on me is an understatement.

My wife and I have a long-term plan to make this dream a reality and I often daydream about it.  When I wrote a post asking “Why Do We Place Our Happiness in the Future” I dissected that dream into components that I could actually incorporate into my present.  When I saw this small, trailerable, salty looking pocket cruiser I realized that this was an opportunity to bring some of that future dream into the present.

Living the dream

And that is exactly what we did.  Our first trip was a daysail on the Hudson.  We put her in at a small rundown yacht club in Tarrytown.  It was the first time I had ever backed a trailer down a ramp and only the second time I had stepped the mast and setup the sails.  With a yard full of onlookers the pressure was on and somehow I got her in the water, the family on board and before I could wimp out I pushed away from the dock and started motoring out of the marina.

Before long we had the sails up, the engine off, and were enjoying a nice sail under the Tappan Zee Bridge.  Upon our return I realized that if getting the boat off the trailer seemed difficult than getting it back on was a nightmare.  I struggled to get the trailer to the right depth and to get the boat lined up properly.  I must have pulled her out and put her back in for adjustments five times before I got it right.  As I pulled away from the boat ramp several people came running out of the yacht club screaming for me to stop before the mast knocked over low-hanging power lines.  I obviously had been profiled as a novice.

With our inaugural voyage under our belt our confidence increased and over the remainder of the summer we sailed the boat three more times.  One more time on the Hudson, sailing out of JFK Marina in Yonkers with views of the George Washington Bridge and one time out of Glen Island Park, sailing in the Long Island Sound with views of expensive yachts and homes all around us.

Then we had the crazy idea of pulling the boat up to Maine for our week long Labor Day vacation.  This decision goes down in my personal history as one of the biggest moments of “I didn’t know how much I didn’t know.”

Luckily we made it all the way to our destination without any major issues and a few days later we put her in at Lake Damariscotta and enjoyed a magical day on the water.  We tacked back and forth on the small lake with light winds and no waves.  A small seaplane came over the horizon and landed a 100 yards from us to all of our amazement before taxiing around the lake and taking off again.  We anchored in the lee of a small island and my daughter and I swam the 10 yards together to visit a small barking dog that belonged to some other boaters that were exploring the island.  She was so excited about it all.  The sailing, the swimming, the dog.

I was living my dream.  Here I was sailing on a beautiful, secluded body of water, my wife and children were enjoying themselves, and everything was going so smoothly.  I couldn’t have been more happy with myself.

I don’t think we’re dreaming anymore

As the sun began to set we made our way back to the boat ramp and after tying the boat up I ran up to get the trailer.  I quickly backed it down the ramp and tried to crank the boat onto the ramp using the winch.  It wasn’t working.  I could crank it as hard as I could and as soon as I let go it would just unwind.  A memory of the winch making a loud noise when I put the boat in bubbled up from my subconscious and I realized that I might have a real problem.

I told Kelly to hold tight, she was hunkered down in the cabin with two cranky kids (how quickly the tide turns) and I knew I needed to figure this out quickly.  I pulled the trailer back up to the parking lot so that I could work on the winch.  One of the gears had popped out of position and I realized that I needed to disassemble it and put in in the proper position.  I reached for my limited supply of tools and after 30 minutes of wrestling with the winch I thought I had it working again.

I ran down to the boat ramp to make sure it was open and was greeted by a very angry boater.  As he cussed me out for being so inconsiderate to block the entire boat ramp by leaving my boat tied to the dock,  he proceeded to backup, load, and pull his boat out of the water in minutes.  He drove off before I could react and seeing Kelly and the kids waving emphatically at me from the dock I knew I needed to get going.

This time the winch worked and I was able to get the boat back on dry land.  I went about the process of lowering the mast and packing away all the gear.  Of course the angry boater who had just ripped me a new one was doing the same thing to his boat just yards away.  Before he left I did muster the strength to walk over and apologize.  The truth was that it was inconsiderate that I tied up the dock for that long but I hadn’t even thought about it in the moment.  His deep frown seemed to soften slightly as he climbed in to his truck and drove away.

The sun was fully set as we pulled onto the country road leaving us with about 20 minutes of daylight.  Our vacation home was only 15 minutes away and then it was going to be a rush to pull together dinner and get the kids ready for bed.  All of a sudden I heard a loud noise and felt the car react.  I looked in the side view mirror and saw smoke coming out of the left tire on the trailer.  I slowed as quickly as I could and pulled over as far as possible which left me more in the road than off it.

I looked at Kelly.  She looked at me.  “Do we have a flat?” she asked. “I hope its only a flat.” I responded.  I had seen the way the tire and rim was tilted.  I was pretty sure a flat tire shouldn’t be angled 30 degrees.  A quick look under the trailer confirmed my suspicions.  The axle was broken…

“Do you think we could just leave it here?” I asked Kelly.  “Do you mean, go back to the house and call for help?” she replied.  “No, I mean leave it here and never come back for it.” It was a good thing that Kelly stayed calm and level-headed because I seriously was about to do something rash.

She must have known that I was right on the verge of losing it because she took charge and said, “Well, I guess we need to call someone to come tow us.”  It was that simple really.  All we had to do was call for help.  It was going to cost us some money to pay for the tow and to fix the trailer, but it was just money.  She helped me realize that we were all safe, that this was a fixable problem, and that we would get through this together.

We started making phone calls and before long a slight wiry man with a cigarette hanging out of the side of his mouth and his foul-mouthed wife were wrestling our boat and trailer onto the back of his flatbed truck with come-alongs.  As the truck pulled away with our boat heeling precariously to the right we wondered if she was going to make it to the repair yard or roll off the truck into a ditch.

A wake-up call

The repairs were completed just in time for us to pull her all the way back to New York.  This time I asked the mechanic a lot of questions about what I could do to increase my chances of making it all the way home without anymore difficulties.   The more we talked, the more I realized how poorly prepared I had been taking this boat and trailer on a long distance trip.  With hindsight I can say it was stupid and dangerous to pull this trailer up to Maine given the amount of knowledge I had about trailers, the condition of the trailer, and the lack of tools and knowledge I had available to service the trailer if anything went wrong.

When we got home safely I parked her in the driveway, covered her with a tarp and prepared her for long-term storage.  At that moment in time I would have happily sold the boat to the first person who made an offer.  That is why I was so surprised to find myself recently deciding to tow the boat and trailer 3000 miles across the country by myself.  It wasn’t easy coming to that decision and I will share the details next week…

This is first part of the story.  Read the second part to get the rest of the story.

If you enjoyed this post you might also enjoy:
Standing on the Shoulders of Giants
Damn It Feels Good to be a Daddy
Kelly and Jake: Our Dating Story
My Baby’s Momma is a Badass

Posted in: Personal