Zen and the Art of Trailer Maintenance

I overheard the engineer
Say something ‘bout the landing gear
And there’s no way that bird’s going to fly…
So there’s no plane on Sunday
Maybe the one come Monday
Make the best of a bad situation
Is all you can do…”

Jimmy Buffett

July 23rd

The day I have been waiting for since I started building Grey Fox in 2017 has finally come… I’ve loaded up the boat on the trailer and am heading up to Brooklin, Maine for 4 days of sailing in one of the greatest places on earth to sail a small boat! The Calendar Islands Yawl was designed for coastal cruising in Maine, and that’s what I have been dying to do with it. 

I’ve recruited my old college roommate John to join me as crew.  He’s flying up from Washington DC and I will pick him up at the Portland airport on our way Down East. We’ll be sailing in the “Small Reach Regatta”, a rendezvous and not really a regatta, where over 65 small sail-and-oar boats get together and sail for three days in a friendly, non-competitive and truly photo-worthy fleet.  No engines allowed.

Yesterday I sailed the boat around from its home base at HHYC to the nearest boat ramp and put it on the trailer, and spent most of the evening getting it ready for the 450-mile drive to Maine and packing all the camping equipment into the car.  So this morning, I’m ready to roll.   EXCEPT…

As I make one last check of the trailer and the boat before I roll out the driveway, I am confronted with a very flat tire on the trailer.   No big deal, I have a spare, so I get out the jack and wrench and proceed to remove the offending not-so-round wheel. But the nuts are rusted on tight and despite huge efforts, the application of an inordinate amount of foot-pounds of torque, and a whole lot of swearing, I can only get two of them to even turn. But they just turn and turn and don’t come off.   Rust-welded together and now with the threads stripped.  JUST GREAT… I have a flat and I can’t change it.  

Since I can’t get the tire and wheel off, I try inflating it to see if I can find the leak.  It seems like the tire is not seated on the rim and is leaking at the bead.  I try reseating it by hand and pump it up with my trusty bike pump.   Listening closely, I don’t hear any leaking air.   Just about then I get a text message from John that he’s about to take off and will be in Portland in a couple of hours.  I text back that I had a flat but it seems like a slow leak so I’ll hit the road, bring the pump with me and hope for the best.

About 3 miles from home and before getting on I-95, I stop and check the tire.  It seems fine; maybe this will work.   I get on the freeway and head off.  At the first rest stop in Connecticut, about 20 miles from home, I stop to get gasoline and check the tire.   Before I even get to the side of the trailer with the previously flat tire, I see mud all over the OTHER wheel.   Looking closely, i see that the mud is really grease, and the bearing is coming apart.   SONOFABITCH! I can’t bike-pump my way to Maine with a bad bearing. 

With visions of the wheel coming off at 65 miles an hour and my boat getting wrecked, I quickly abandon any hope of getting Grey Fox to Maine today.   I decide to try to make it the 20 miles back home and figure out a plan from there.  I make it back home without calamity, but Grey Fox is stranded there. This trailer is just betraying me.

OR… have I been betraying it?  I’ve had it for 5 years and have never done a lick of maintenance on it.  Those wheels have been dunked in salt water at least 30 times.  Every time they are submerged they go through a hot-cold shock that causes the grease to shrink a little and allows seawater to get in.  I guess you’re supposed to grease those bearings at least once a year.

I maintain my boat to a tee. I fix every scratch on the boat and inspect it closely almost every time I use it.  Folks at our club give me a hard time for being such a stickler, and think I treat the boat better than I treat my wife.  (I don’t think that’s true, they both get pretty good attention).  But I completely neglected the trailer.  What a … dumbass.

Just about the time I pull back into my driveway, another text from John informs me that he has just landed in Portland.  I call him to speak live.  “Sorry pal, but we have a major problem.  The wheel bearing is shot and it will take at least a couple of days to get it fixed.  As my son’s favorite song from his favorite off-Broadway show ‘Spring Awakening’ goes, ‘here’s the moment you know you’re totally f**cked.’”

“Didn’t you say there are going to be 65 boats at this event we’re going to?  Don’t you think we can bum space on some of those boats?” offers John.

“You’re right – I’m sure we can find boats to crew on. That’s the solution.  Sometimes you’re pretty smart. I guess we’ll go boat-less and hope for sympathy from the other boat skippers.”

I proceed to park the boat and trailer in the driveway.   All the camping gear is in the car, so all I need to do is remove some boat stuff that I don’t need from the car and I’ll be off.  Hmm… don’t need that big anchor.  30 minutes later I text John and tell him I’ll see him in Portland at around 4pm. He’ll have to find something to keep him occupied for the next six hours. 

Freed of the trailer and the mental burden of stressing about how to get it repaired, I’m off and making about 55 knots Speed Over Ground in the Toyota land yacht.  I roll into Portland at 4:30 and pick up John, and before 8:00 we’re in Brooklin.  We check in at the campground and then head to the Brooklin Inn, the only food establishment in town that’s open on a Tuesday, for some dinner.  We made it!  Just without the boat that was kind of the whole point of the trip.   But we’ll find other boats to ride.  We’re making the best of a bad situation.

Of Gatsby and Obi-Wan Kenobi

“I will take the boy, and watch over him.”

Obi-Wan Kenobi in one of the Star Wars movies

June 23rd

Yesterday’s northwester is blowing itself out, and this afternoon the forecast is for 8-10 knots of it, an amount that is perfect for Grey Fox and manageable enough for the skipper to take out his nephew for a Sunday afternoon sail. Nephew Greg (16) has done some sailing at summer camp and most recently with the sailing club at high school.  Since his family doesn’t have a boat or any access to the water, I suppose he is lucky to live in a town with lots of sailing (hence the high school club can find boats – nice ones, 420s no less – to sail at that bigger fancier yacht club in Larchmont) and a salty (or is it eccentric?) old uncle with a saltier and more eccentric boat.  His mother, who doubles as my sister, is pleased to have me offer to take him out, and only asks that I refrain from capsizing the boat and him.  I guess she has heard that that is a possibility with a small keel-less boat.

We get underway mid-afternoon to a delightful offshore breeze and take the route of least resistance, heading south on a reach in the direction of the city.  Playing sailing instructor to Greg’s apprentice, I let him do the steering and sail trimming. 

Not long into our sojourn I point out to him that he needs to pay constant attention to sail trim, as the sails are sheeted in way to tight.  “If you want to win those sailing club races you’ll need to pay more attention to your sails.  In a shifty breeze like this, it’s a constant process.  Just because you were trimmed right a minute ago doesn’t mean you will be now” says sage Obi-wan Kenobi.  

Young Luke responds “How do you tell they’re trimmed too tight?” 

“Look at your flag” replies the Sage One.  Greg looks over his shoulder at the flagpole on shore.   “Not that one, young Jedi. The flags at the top of your masts. That’s why they’re there – so you can see the wind direction.  Also look at the streamer trailing off the end of the yard.  It gives you an idea of the direction the wind is leaving off the leech of the sail.”

Flags and streamers

“Oh, so that’s what that streamer thing is for” acknowledges the apprentice. 

“Well, yes, plus it looks cool – how many other boats have one of those?” I reply.  Following this remonstration, young Greg tightens his concentration on getting the most out of the boat.   See the steely-eyed determination in his eyes:

I guess I better pay attention…

Even though the wind is lightening up pretty rapidly, our reach has us off of Hart Island, Bronx in no time.

Passing the gong buoy off Hart Island

From there we head almost dead downwind across the narrows to Great Neck on Long Island, which forms the western side of outer Manhasset Bay.   It’s also the “West Egg” in The Great Gatsby, where Gatsby and the other “new money” folks lived. From there we scoot across the bay towards Manhasset Neck or Sands Point, which would have been “East Egg” in the same book, and is where the old money lived and where Gatsby aspired to be.  I tried to read F. Scott Fitzgerald’s book once but found it so uninteresting that I never made it through the whole thing.  But I do remember that in the book, the folks in East Egg had a great view of the Manhattan Skyline.  Since we are now pretty much in front where Daisy’s house and dock would have been, I can confirm that the East Eggers had a great view:

Looking southwest from East Egg

The skyline today is certainly way more dramatic than in Gatsby’s/Fitzgerald’s Roaring 20’s.  Partly because today’s golden era is even more roaring than back then for the top 0.01%, and they are the market for the new ultra-high rise apartment buildings that are currently transforming the Midtown skyline.  Somehow I suspect that these sky-high multi-story “apartments” are in addition to, rather than in lieu of, Gold Coast mansions… If you have billions, why not have both?  A hundred-million $-plus pied a terre in the city and a weekend estate in the Hamptons.   Not to mention a yacht, a ski chalet in Aspen, a private island in the Caribbean and of course a jet to get you to and from all of them.   Well, I’ve got my yacht…

Back to the sailing… by the team we get near Daisy’s dock in East Egg, the wind dies completely.   Greg starts to get antsy.  “There’s no wind.  We’re stuck.   We’re going to have to row all the way back to Larchmont”.  Considering that the distance to Larchmont is at least 4 miles, and I just did that cross-sound row last week, I’m not in a hurry to take in sail and get out the spruce breeze.

“Patience, young Jedi. The wind will fill in.  In the meantime, we’re not drifting onto rocks, or running out of daylight, so let’s just sit back and relax,” offers Obi-wan. “Or, if you prefer, I can tie you to the mizzenmast and lash you with a cat-‘o-nine tails as an offering to the wind-god Aeolus, and see if that will rustle us up a breeze”.   Greg looks at me like I have three eyes, which is fair, because he clearly hasn’t read my prior post here, “Puffs and Gusts”.

Sure enough, before long the afternoon Sound southwesterly comes in and we are moving smartly northward towards Larchmont.  We pass by Execution Rocks and I spot a couple of kayaks a half mile off.   Thinking I recognize the color and shape of the boats, we alter course to intercept them.  It’s Jean and Bea, two of the hardest-core kayakers in western Long Island Sound and fellow kayak pals of mine from HHYC.   I take the helm from Greg and head over to rendezvous with them. 

When we get alongside I hand my waterproof camera to Bea and ask her to snap a few photos of us.  I don’t have any pictures of the boat taken from not on the boat.   A kayak isn’t the best platform to shoot photos from, but Bea gives it a try.  We make two or three loops around her in Grey Fox to give her a good angle, and she comes up with some pretty good shots.

Photo session complete, I re-raft with Bea to get the camera back and then offer to race them back to HHYC.  In light air or going upwind, they would fly right by Grey Fox, but by now the breeze is up to maybe 8 knots and on a reach we are doing almost 5 knots, leaving our 4+ knot kayakers slowly slipping away. 

Gusts and Puffs

June 24th

After two weekends away from the water, I’m back on Long Island Sound in Grey Fox.  I was in the Dominican Republic doing some volunteer work with #BridgestoCommunity, along with a small group of fellow travelers/volunteers from the Bank.  It’s Global Volunteer Month at the firm, during which all employees are “encouraged” to spend an afternoon volunteering with any of a wide range of charities and non-profits.  Our pick-up group of volunteers went the extra mile, each individual using a week of their precious vacation time and spending a substantial portion of their own money to make the week-long trip to the D.R., where we built housing in a remote (and fairly primitive) village in the central highlands.  Don’t tell Elizabeth Warren, it’s not consistent with her narrative that all Wall Street bankers are evil.

Back to the log of Grey Fox…

After two weeks of landlubbering, I was anxious to get back on the water.   Saturday’s forecast was for strong and gusty winds out of the Northwest.     Windfinder.com, the oracle of weather prediction for kitesurfers,  windsurfers and small boat sailors, predicted 12 knots with gusts to 22 throughout the day.  That’s on offshore breeze in my stomping ground, and the perfect direction for a reach up the coast to Great Captain Island in Greenwich, Connecticut and then a reach back home.  

I hit the water at about 7:30am with a plan to sail solo to Great Captain, 7 ½ miles away, drop the hook or beach the boat and take a breakfast break, and be home before noon.   From the cove, the wind looked modest.   Even though it would be stronger once I got a little further out of the lee, it felt pretty manageable.  So I tied in one reef and was on my way.   Crystal clear sky, bright sun but only 70 degrees, and smooth water made for great sailing.  I sailed about a mile with shifty and puffy winds, but even the puffs only got up to maybe 12 knots, so I hove-to and shook out the reef.

Sailors are a superstitious lot, and I’ve seen them go to elaborate lengths to try to rustle up wind.   When I was on the Esmeralda, the Chilean Navy’s 310-foot tall sailing ship, back in my younger Navy days (i.e. 1985), we became becalmed off of Tierra del Fuego while trying to round Cape Horn from Atlantic to Pacific.  Yes, BECALMED off of Cape Horn.   THAT never happens.   But it did.   After about 24 hours of flopping around, and in the middle of the night, the powers that be mustered the entire crew on the afterdeck (“la popa” in Spanish) and proceeded to make an offering to Aeolus, the god of wind.   Aeolus was played by one of the senior chief petty officers of the ship, who was dressed the part and from shouted through a bullhorn from atop the mizzen boom shouted that the required offering was that the youngest cadet onboard be tied to the mizzenmast and flogged with a cat ‘o nine tails.   Fortunately, it was all for fun, the cat o’nine tails was made of yarn, and the flogging was not real.  But Aeolus declared his satisfaction and promised wind before daylight.  

Lest the reader think that the complete digression in the prior paragraph is completely made up, or maybe a semi-true story as I am known to occasionally tell, (1) I have photos to prove that it’s true, and (2) it was a just a lead-in to the following:  If shaking out the reef is a strategy for getting more wind, it really worked for me today. 

Completing the digression, the cadet sacrifice worked, and by the morning we had 20 knots and growing.   Even better, the wind was from the east (not the prevailing wind) and pretty soon we were flying around the Horn with 40+ knots of wind.  In fact Aeolus overdid it, and we managed to bend a spar and blow out several heavy canvas sails during the next 24 hours. 

Grey Fox’s skipper (then a lowly midshipman) rounding Cape Horn aboard Esmeralda after Aeolus delivered mucho viento… June 1985

A little gratuitous flashback there. Besides, I needed an excuse to throw a photo into this post and I sure didn’t get any sailing today because my hands were kind of busy. Back to Long Island Sound…

Within ten minutes of shaking out my reef, the wind was up to 12 knots and the gusts were getting a lot stronger.  Ten more minutes of struggling to hold the boat level, and I hove-to again to tie that reef back in.   With pretty strong gusts as this point, tying in the reef was trickier than I remembered. My reefing rig requires me to put a reef hook on the forward end of the boom through an eye in the tack of the sail – pretty easy – but then to do the same thing with the clew of the sail to the hook on the after part of the boom.    You can only do that with the sail more or less amidships, and with the gusty wind, the boat didn’t stay bow-to-wind.  Even with the mizzen sheeted in tight, and with the drogue I keep in the bow thrown into the water, it wanted to tack back and forth.  As soon as the boat would veer off the wind, I would have to let go of the boom or otherwise I would serve as a human cleated-down-mainsheet.  And we know (see prior posts) what happens with a cleated-down mainsheet in gusty winds… a swimming party.   Having a strong interest in avoiding swim practice today, I had to let go of it several times before I finally got the reef hook seated in the clew.   

Another two or three miles of exciting and truly athletic sailing – hiked out over the windward rail and with both hands working the mainsheet and the tiller constantly – the gusts got to the point of being a little scary. Unable to hold the boat up with the sail full, I was forced to half-luff which knocked my speed down significantly.  I estimate that the gusts were getting up to 25 knots.  I decided that discretion is the better part of valor.  Off of Playland in Rye, about 2 ½ miles short of Great Captain but still almost five miles from home, I decided to head back. 

The ride home was a hoot as it was enough of a beam/broad reach that I could carry that amount of sail, even though I had to spill air frequently.   In the big gusts I would try to bear off enough to minimize the healing moment, and the boat actually got well above hull speed.  The GPS showed above 8 knots during those surges.

If I had had to make any headway on a close reach, I would have had to tie in a second reef and furl the mizzen.  I probably should have anyway, but I was managing the beam reach as is – barely – and didn’t want to stop to reef. With wind that strong I would have had to drop the main all the way to put in the next reef (I wasn’t going to risk trying to do it with the sail still up) and it felt like it would be more work than just manhandling the boat the last couple of miles.

In no time at all I was back to Larchmont. That was an exciting sail… But with never any hair-raising I-almost-capsized moments.

A surfeit of crew members

June 3

Son Jeffrey is home for the weekend from college in Boston.   He’s spending all summer in school.  He had a tough sophomore year but seems to be getting back on track, and summer semester will help him get caught up. 

I would be flattered to think that he came home just to see dear old mom and dad, but the primary reasons for the visit are made clear when he texts me mid-week and asks “how many people can you fit in the boat?  Because I’ll have my new girlfriend Adri with me as well as my high school friends Eli and Emily, and we all want to go sailing.”    “Four really” is my reply.  “I don’t know where a fifth would even sit”.  Maybe I can take them out in shifts.  Jeffrey has done some sailing in his high school days, and even got to where I would let him take the dory out by himself if the weather was good, but he’s only been out in Grey Fox once and doesn’t really know how to rig it or sail it.   So like it or not, they need the old guy to take them out. And I’m thrilled that Jeffrey wants he and his friends to come out with me in the first place.

The kids go down to the club with their lunch, and I get there around 3pm.  It’s warm and sunny with maybe 8 knots of wind, again out of the north, and forecast to hold through the afternoon.    Mild enough conditions that I think we can handle five people in the boat (none is over 150 pounds).  It  will be more fun for Jeffrey with his whole crew.  We head out and the conditions seem perfect for a trip across the sound to the beach at Sands Point.  With 4 neophytes on board, I wouldn’t think of going that far from shore and home base if the weather weren’t pretty sure to stay tame.

Heading out…
I don’t have any pictures of the boat sailing, since I’m always on it. Pat got this cellphone snap from shore as we headed out.

The sail over is delightful, with enough wind to move the boat but not enough to create any excitement.   Even with 5 people on board we have plenty of freeboard and the boat handles the boat wakes we encounter with aplomb. The time it takes get to Long Island is certainly more time than I’ve spent with Jeffrey and his friends in a long time, and even though I’ve welcomed them onto my boat it also feels a little like they’ve welcomed me into their circle.   

Jeffrey & Adri
Emily has found the best seat on the ship

As we approach the beach at Sands Point I hand the tiller to Jeffrey and get the anchor ready.  The wind has dwindled so it’s a slow motion approach to the beach, which makes it easy to drop the hook only 75 feet from shore.  The wind blows us stern towards shore and I cleat the bow anchor line with the transom in about a foot of water. I let down the mainsail carefully, without bashing anybody in the head. I order seaman recruit Eli to be the van of the landing party, and he jumps off the stern into the knee-deep water.  I hand him the stern anchor and he takes it ashore and digs it into the beach.  Moored!  The boat will stay afloat in the rising tide, no beaching required. 


While we’re poking around the beach, the wind completes its fizzle and pretty soon it’s mirror calm.  I was hoping a southwester would fill in and help us home, but hope isn’t a strategy.  We’ll need to use the inboard motor – a.k.a. Dad with a pair of nine-and-a-half foot oars.  Looking at my watch I can see that if we’re going to be rowing the three and half nautical miles home, we should get going to be home before sunset.  So I round up the crew and off we go. 

Eli mans the oars so I can deal with taking in the anchor.  It takes him a while to get the hang of it – those ARE some big-ass oars – and we never get much above 2 knots.   After 15 minutes of effort and maybe a quarter mile gained, I relieve him.   Thank you for your service, but sunset is arriving on time tonight, and I didn’t bring the running lights.

There’s still a long way to go, but I like rowing.   It’s not as easy with 750 pounds of crew in the boat though!  The Mk 2 rowing footrest works well in its first real test.  With just me in the boat I can average about 3.3 knots but with this configuration I’m lucky to average 2.75, so it’s going to be an hour and half of steady exercise. It’s good for the old man.

About a mile from Larchmont, one of the larger sailboats that has been trying to sail gives up and motors towards us.   Passing us close aboard they ask if we want a tow, but I don’t trust big boats to tow little guys like us – especially heavily laden – safely. “No thanks, we’re getting along fine.”  Maybe the guy on the sailboat’s only experience rowing is with an Avon inflatable or a Dyer Dhow, in which case he would think that we are desperate and stranded.  But Grey Fox was designed to row. Miles. 

Round about 7:30pm we make landfall in Horseshoe Harbor.  The kids scramble off to their next event, and I put away the boat.  I think I’ve earned my beer for the evening!

On the water in a bigger small(ish) boat

May 26th

Memorial Day weekend.  I had promised my father I would come up to Rhode Island where my parents live and help him with the last jobs needed to get his boat in full sailing condition.  So we head up there Saturday and spend the early afternoon getting the sails bent on, the decks and cockpit cleaned, and everything ready to go on his Alerion 28.  That doesn’t take long, and the wind is a perfect 15 knots out of the South, so we take the boat out for a spin.  

Dad is 84 now, and I was kind of wondering whether he was still going to be up to managing the boat by himself or even with one other crew member.   What I had forgotten was how easy the Alerion is to manage.  With a working job with a single sheet led through a deck traveler, and a big powerful mainsail, the boat is perfectly balanced.  Steering with the tiller rarely requires any muscle.  And to tack it all you have to do is put the tiller over.  It’s a keelboat and very stable, so you don’t need to worry about moving your weight around to balance the boat.  It’s easier and considerably less physical to sail than Grey Fox. 

Even though the wind builds up above 20 knots, we feel comfortable sailing out past Newport Harbor and into the fairly open waters of the East Passage of Narragansett Bay, all the way out to Brenton Point, with no trouble whatsoever.  By then the waves are getting big enough to bring some splash aboard, so we turn downwind and head back to the marina just north of the Newport Bridge.  The ride home is fast and exhilarating.  A great boat, a great Dad, and a great day on the water!

It’s not a racing boat, but we still like passing other sailboats

May 18th

In Grey Fox’s first season, I did a lot of solo sailing.  There were kinks to work out in the new boat that I was happy to do on my own, and I did a really poor job of planning ahead, which is necessary if you want other people to plan ahead and join you for a sail.   So this year I hope to do much less solo sailing and get more friends or accomplices out with me.  Before I had a boat of my own I always considered it a treat to be invited to go out on someone else’s  boat, yet was surprised how rarely an invitation actually materialized, even with lots of boat-owner friends, including friends who would often say when we saw them somewhere “you ought to come out with us” but never actually extended an invitation. I hope not to be that type of boat owner this summer!

So for my second weekend outing this season I talked my kayaking buddy Rick into coming sailing with me.  Rick is a barrel-chested bear of a man whose average paddling speed keeps me gasping for air to keep up.  He used to have a sailboat before wife and kids and responsibilities came along.  He’s free this Saturday so we make plans to get underway at noon.

The wind is out of the north, light and variable, but as long as it’s not nil those are conditions that Grey Fox likes. We start out heading south for Execution Rocks, ghosting along in the whispers of wind.  It gives Rick, who hasn’t held a tiller in years, an easy period to get the feel of things.  As expected, the northerly dwindles as the day proceeds, and pretty soon we’re just about becalmed.  With no hands needed to sail the boat, it’s time for the sandwiches and beers we brought along. 

Lunch finished, the first signs of a afternoon southwester arrive, first with a few ripples that tease more than they fill the sails.  Once they get a little more steady, we abandon the idea of continuing to Execution Rocks (it’s dead upwind and too much trouble) and head north towards Milton Harbor in Rye.  As the wind fills in to 4 or 5 knots we have the boat moving along pleasantly at 3 knots or more.  Tons of sail area and a very light weight boat are the magic formula.   With the wind pretty consistent now but still very light, I can tie down the tiller and cleat the mainsheet, and for a while we’re on autopilot.

After a tour through the Milton Harbor mooring field we jibe around and head back towards Larchmont.  By now a number of 30- and 35-foot sailboats are out, including some pretty sleek and fast-looking racing designs, trying to move in the whispering winds.  We take great pleasure passing several of them in the light air and smooth water.  With any bigger waves or more wind they would exert their hull-speed dominance, but for now we’re the fastest sailing craft in the area.  Foxes are supposed to be fast!