Thursday, February 8, 2024

My Sailing Career

My Dad took me sailing for the first time in 1978, a resort that used to be in San Diego called Vacation Village rented out small metal hull sailboats, 10' and 14' long, the smaller of them didn't even have cleats for the sheets, you had to hold them.  The dock hand gave us a 10 minute lesson on how to make it go.  I was captivated!  I sailed out of there a few more times, but even then I knew I wanted more.

Amazingly, I found this ancient video of those little boats! 


The next place I rented from indirectly taught me how important it is for the bottom to be clean; theirs were not, at all!  Of course it took a while (and some experience with better-maintained boats) to put it all together, in fact, I almost gave up on sailing!  I read and re-read books on theory, it just wasn't adding up!  

Their dock was in Quivera Basin, to get back from Sail Bay, you had to tack under West Mission Bay Drive bridge.  Typically there was a 20 degree wind shift under the bridge, so you had to bear away, heading straight for the pilings, then tack to avoid ending up in irons.  If the tide happened to be incoming, a blown tack would get you swept back a hundred yards or so before making any way again!  It took me a few tries but I made it!  (Those that did not had to pay extra for their skiff to tow them back.)

The next time we went out we wanted to leave the bay, which required their biggest boat (19' or 21') fitted with an outboard.  We tried to tack out Mission Bay channel without much success -- blowing a tack as you near the breakwater rocks is unsettling!  So we motored to the entrance, assessed the wind, trimmed the sails and... went no where against the tide!  I said screw this and headed back to their dock for the last time.  It wasn't fun.

Luckily, the next place I tried, Mission Bay Sports Center, was way different, night and day!  The first time I took out a Hobie 16, I lost count of how many trips from end to end of Sail Bay I made, and took it back 20 minutes early, exhausted (capsized a couple of times) and thrilled beyond words!  (At the other place, one trip to the end of Sail Bay and back, then tacking under the bridge took 90 minutes.)  I became a charter member of their brand new club, which gave me unlimited use of their fleet, and I sailed the hell out of it!

In addition to their fleet of Hobies and Prindles, they had a J-24 and a Catalina 27 -- needed a 2' tide or lower to get under the bridge!  I made my first passage with a destination in that Catalina, from Mission Bay to Glorietta in San Diego Bay, using the training chart from the Coast Guard Auxiliary Coastal Nav class I had just completed.  We stayed the night in the anchorage.  A few hours into the trip back, we slammed into thick fog, zero visibility.  With no visible landmarks all I could do was plot course and speed, and for extra caution, every time I saw kelp I sailed west for 15 minutes.  After trading sound signals with the Ocean Beach pier for 20 minutes, before figuring out what it was, I knew I was close to the entrance.  I was going to sail west to kill some time safely, when the fog magically lifted, and the white knuckle flight was over.

I loved that club, learned an absolute ton and gained a lot of confidence!  All the theory now made perfect sense!  But into the second year they changed the usage rules, so with a fond farewell I joined another club, in San Diego Bay, called Harbor Sailboats.  I ended up trading them IT consulting for sailing time on club-owned boats, my favorite of which was an Islander 36 named Vitamin Sea.  I sailed her to Catalina many times, and to Ensenada a few.  

I challenged the ASA exams up through 105, took an on-the-water class for 106, then ended up working on their dock and teaching intermediate sailing for two seasons.  One class, as we were covering anchoring, in the now-gone anchorage off of Shelter Island, the anchor got snagged on some derelict ground tackle.  After trying many tricks I was almost ready to tie a fender to the rode, but finally got it up enough to cut and twist it free of the junk.  At the dock I started to apologize for getting back 45 minutes late, but they all insisted it was the best class ever, watching me problem solve instead of going through a canned lesson.  Their perspective was interesting, I discussed it with my manager and the owners, but we concluded that any attempt to fabricate would seem contrived.  Sailing classes are not equal, some students get luckier than others. 

Vitamin Sea was aging, and had a lot of charter miles behind her, we had a few mishaps.  One trip coming back from Ensenada we ran into some weather, her mainsail split at the second batten, in 35 kt winds  (it was really old and beaten.)  A few weeks later she was sporting a new main, it was amazing, and brought home more of what I had read about sail trim. 

Another time I took Vitamin Sea and a couple of fellow employees on an evening bay cruise, the engine oil gelled in the filter and the engine seized!  We sailed back to the marina, where the wind died completely just as we were about to turn into the fairway.  We keel-skulled her into the slip.  Because it gelled beyond the pressure sensor the alarm never went off.  They had the oil analyzed and were told it was way beyond maintenance interval, which led to the discovery of a flaw in their maintenance scheduling scheme.  Bottom line, it was not my fault in any way, beyond question.  Even so, one of the owners couldn't make eye contact with me for a month.  

The other owner took me as crew on a trip to La Paz on his O'Day 37, Blackjack, then a year later paid me to bring her back from Puerto Vallarta.  Word got around, I got a couple of other delivery gigs -- fantastic work if you can get it, but I was still trying to document enough time to get my license.  It wasn't enough to pay the bills.

I got my first real programming job in 1989, working for a DoD contractor.  I remained a member, sailed once or twice a year, raced consistently for a few seasons, and even kept my membership when I moved to the Central Cali Coast in 2005... but after a year of failing to make it back down to go sailing, I had to let it drop.  I rejoined in 2014 when my dad passed away, to scatter his ashes at sea as he wished, but my siblings weren't willing to part with his remains.  My brother offered to divvy them up, like a bag of weed or something, but I had to pass.  I still went sailing with my daughters, we talked about his life... memories... we sort of scattered his ashes symbolically.  RIP dad.  I didn't renew the following year.

I got back on the water late in 2018, I joined a partnership on an Islander P40 called Islero, named after a Spanish fighting bull that killed a matador, located in Brisbane.  It was an awesome arrangement, I discovered the exciting conditions in SF Bay.

(First time on Islero.)


After 3 1/2 years I left the partnership when I bought my Islander 44, to live aboard.  I sailed her from Ventura to San Francisco in September, 2022, slip prices are lower than in So Cal.  I was transient for several months at different marinas, liveaboard permits aren't easy to come by.  I ended up renting slips in two marinas, moving back and forth twice a week, for 6 months.  I finally made it to liveaboard status just this month, at Brisbane.

(My Islander 44, S/V Fine Aft, tied up at Coyote Point Marina.)


I'm now a member of Sierra Point Yacht Club, and the Islander 36 club.  I participate in my club's Beer Can race series, as I continue to learn in the challenging conditions of SF Bay... my story is still unfolding.


(RIP Dad.  Little did either of us know you changed my life forever, on that wonderful sunny San Diego day, out on the water, so very long ago.  Thanks, man!  I miss you!  You may be gone, but will never be forgotten!)