How I Succeeded in Circumnavigating Catalina (Circumnavigation Part Deux)

A sudden gust threw another whitecap over the nose of my paddleboard, slowing me to a stall.  I teetered, hunched down, and dug deep into the foam with my paddle.  I felt like Bill Murray in Groundhog Day.  I still had the bad taste in my mouth from the last time I tried to paddle from Little Harbor to Avalon.  And now, barely out of Little Harbor on my second attempt, I was terrified that I would suffer the same results: a puke-infused failure.  The wind had picked up and the conditions appeared to be worsening.  I was pissed.

“Not this time, asshole!” I said out loud to the wind, and lunged at the water with my paddle.

Paddle 1 (Two Harbors to Parsons Landing):

As I related in my prior post, I tried to do this circumnavigation thing once before, and failed.  One year later, I was making another attempt but this time I picked a couple days I reckoned would be within the best weather window, and give me the best possible shot at it.

This time my boat to Two Harbors had a layover at Avalon.  I was glad because I got to take a look at my final destination, point at the Casino, and say to it, “I’ll see you in two days!”  Along with only a handful of other passengers, maybe 5 of us, we shuttled over to Two Harbors, which took about a half hour. 

The ocean’s surface was calm, the sun was bright, and very few clouds floated above.  It was hot when I arrived on shore, and I worked up a good sweat inflating my board.  I loaded up and I was off, reliving my paddle from the year before. 

The sea on the way to Parsons Landing was calmer this time, and the winds lighter.  Wonderfully, the visibility into the water was outstanding and as I paddled, I could frequently see well down into the water, to the bottom, up to 40 to 50 feet sometimes.  

Large schools of small baitfish were omnipresent as I paddled over them.  Frequently, the school would scatter before me, and in an instant, a thousand tiny splashes would erupt on the surface of the water.  The multitude of eruptions would disappear on the surface in a beautifully choreographed pattern, with the splashes returning to the sea like silent falling dominoes.   

This time, I knew exactly where I was going and remembered the various nooks and crannies of the coastline as I paddled by.  When I came around the corner into the bay just short of Parsons, I could see the large recognizable hunched rock at the western edge of Parsons’ beach.  I settled down into the surf and landed on the beach with no trouble.

I went to work on setting up camp and once again, I had a pleasant day of solitude at the campsite.  With a cold Pacifico in hand (complete with a lime wedge from home), I pulled out my island map and plotted my revenge on the island. 

This time, things would be different.

Paddle No. 2 (Parsons Landing to Little Harbor):

Unlike the first time I paddled from Parsons in the early dawn hours, this time there was no fog at all.  All was bright and warm, and the early sun’s rays were kaleidoscoping into separate slowly spinning shafts of light in the water underneath my board.  I was sweating almost immediately, and within 15 minutes of leaving shore, I stopped to pull off my windbreaker. 

The water remained calm and although the swells were heading toward me, traveling east while I traveled west, they were not checking my way very forcefully.  I paddled at an easy pace, knowing it would be a long day, but not knowing what it would be like on the open ocean side of the island.

When I approached the last few hundred yards before West End, I again paddled into that deep bay with the sheer, gray cliffs that had so impressed me the first time I had seen them. 

The surface of the water in the bay looked like it kept a secret.  It felt deep, very deep.  Unlike the sunlit water leading into it, here the water was black in the shade of the cliffs, and the surface was almost still.  I could not see anything underneath. 

It felt sharky.  You know how it feels when you suddenly feel like you’re being watched?  That odd intuition is probably attributable to an ancient survival mechanism that evolved to keep us alive.  Perhaps there are subconscious cues our brain picks up through peripheral sensory input, and perhaps our conscious brain is not aware of it.  A curious ripple on the water not consciously seen but subconsciously understood and noted?  When those subconscious cues spell danger, the inner brain tips off the outer mind, saying, “Yo, caveman, pay attention or get eaten.” 

So when I say it felt “sharky” in that deep bay, that’s what I mean.  It felt like I was being warned to watch out.  Given that I was on an inflatable board, it was all the more important.  Any exploratory bite from a hungry white on my board would leave me with a serious problem, especially as far from help as I was.  So I listened to my highly evolved brain, and I got the fuck out of there. 

Out of that bay, the ocean changed almost immediately and I was no longer concerned about oceanic predators hurtling out of the deep.  I was now concerned with what was barreling down right in front of me.  As it was the last time I was there, the waves and ricocheting backwash was a real menace.  I was ready for it this time though, and I put my head down and did some work to get around it.

I was around the worst of it in just a couple of minutes.  I paddled close to and around Eagle Rock, this time taking in more of the scenery.  Then I started my journey eastward down the island, about 250 yards offshore. 

Weathering West End

Although the swells were larger than they were on the leeward side, they were easily manageable and I was thrilled that the conditions were so good.  Of course, as I quickly reminded myself, the conditions were this good last year too, at Stage 2 of the mission. 

“Just shut it and enjoy this little victory.” 

“I’m just sayin’.” 


After a few hours, I entered Lobster Bay.  Because I really wanted to know if that same harbor seal was still there, I paddled into the little cove that I had eaten lunch in the year before.  I stopped in the same spot and did the same thing.  No seal this time.    

After that little diversion, I moved past Catalina Harbor, again chose a direct route to Little Harbor, and made it there without incident.  Although my watch died on me toward the end of the paddle, it took me about five hours (with breaks and all), and it was approximately 13.5 miles of paddling.  I slowly glided into the harbor, pretty spent. 

Eventually, after I had gotten my gear to my site and set up my tent and clothesline, and after I had showered off and cracked a beer, an older couple came over to talk.  They expressed shock and dismay that I had paddled from Parsons, and genuine concern when I told them I was paddling to Avalon the following day.  When they left, shaking their heads, I felt a pang of fear that they were right, and that what happened to me last year was about to happen again. 

I ate dinner over a thriving fire in a cement fire ring.  I slowly rotated my kielbasa sausage and while the fire danced, I tried to picture finishing the job the following day.  I saw myself rounding the end of the island, and paddling into Avalon, saluting the casino and falling into the water in celebration.  I thought about staying further from shore this time to avoid all the backwash, to paddle far out, , which would take  longer but would ultimately be smoother.  But tacking on miles to an already 18-mile paddle did not seem wise. 

“Stop overthinking it.  Just go to sleep.”

Paddle No. 3 (Little Harbor to Avalon):

But I couldn’t sleep.  I woke up repeatedly, listening intently for the waves, wondering if the surf had gotten louder, then wondering if the wind was picking up.  I would check my phone to see what time it was, thinking that I should really get on the water while it was still dark to give me as much time as possible.  But then I would see it was only 1am, then go back to sleep, and then repeat the sequence all over again. 

I finally got myself out of the sleeping bag at around 6am and walked gingerly in the dark to the porta-potty.  My legs and back were sore.  My hands were swollen.  With my headlamp on, I boiled water for tea and oatmeal.  I then downed a Kind Bar and dried mango.  No dehydrated breakfast eggs this time. 

By the time I launched into the harbor, paddled around the surf, and ventured out into the open ocean, the sun was suddenly visible.  To my dismay, I noticed two things: first, the wind was whipping it up out there; second, there was a rather large western swell coming toward the island at a perpendicular angle, which meant that once again, there would be significant backwash once these swells hit those cliffs.  I was far too familiar with this problem. 

I told myself that I would rather contend with the wind than be buffeted by the backwash so I steered a course well out to sea.  As I did so, I took some comfort in the fact that I seemed to be having less trouble staying on my board this year.  It was not quite as rough this time around. 

But then, as I came even with Ben Weston Beach, which is just southeast of Little Harbor, an extremely persistent on-shore wind went to work destroying my life.  The wind tore into me, as if every molecule of air on the island had nowhere else to focus on.  Seeing that I was the only living or non-living thing protruding from the surface of the ocean for miles, every one of those molecules decided to fuck with me.  That is what it felt like anyway.  It felt personal.

“This was not in the forecast,” I yelled out.  “What the fuck?!”    

I could not figure out what was going on.  The wind came out of nowhere.  And it was sudden and gusty.  I looked at where it was coming from on shore, and noticed that there was a sort of canyon on both sides of the beach.  I was in the middle of this wind tunnel, and since the sun was heating up the island for the first time today, I was in a vortex of heated air rushing off the island.  At least that was my theory.

All I knew was that I was now being pushed hard to my right, and going to the right meant going to the Hawaiian Islands.  I did not have enough food for that.  To counter the wind, I started paddling hard on the right side, to keep my board going straight.  And it was all right paddling for about a half mile.  I told myself that I would just need to get around the bend of the island at the 4-mile mark, and I would be home free with a western swell at my back pushing me toward home. 

And then the movie Groundhog Day came to mind.  I was now Bill Murray, trapped in a replay of a previous day in my life.  Last time I was out there, I had that same thought about getting to the 4-mile mark and it did not work.  If this wind kept up, and if the waves got worse, I’d be knee-paddling and yacking all over again.  And if that happened, I’d be turning around and telling everyone how the island kicked my ass again. 

But I did not let my thoughts get that far this time.  I decided that this was a battle with my own mind, not with the elements.  The wind would stop when the sun gets higher, and once I got to the 4-mile mark out of Little Harbor, this swell will absolutely be my friend.

“This too shall pass,” I told myself.

After about a half hour, the on-shore wind did stop.  And then I hit the fabled corner at the 4-mile mark, a spot I did not reach the last time.  I had turned the corner on the island and started heading east toward the sun.  The western swell was finally at my back, and the entire feel of the ocean changed.  The wind vanished, the turbulence was gone, and it was as if I was running down a smooth and calm river, with periodic swells propelling me forward. I was going with the flow and all was right with the world. 

A huge smile spread across my face, because I knew, right then, I was going to make it back to Avalon.  Even though I still had 14 miles to go, there was not a doubt in my mind that I would make it this time.  The fear disappeared with the wind, and I paddled dreamily, with minimal effort for several miles as I whipped around the island with the current and swells at my back. 

I silently passed over the most gorgeous and abundant kelp forests I had ever seen, feeling like a voyeur in this little known marine world.  Innumerable fish of all sizes lollygagged in, around, and through the tall brown stalks.  A flying fish shot out of the water a foot from my board, spread its bat-like wings and skittered over the water fifty yards to my right, where it retracted its wings, and dipped back in the water.  The entire experience, for about two miles, was so beautiful and even sort of magical; it was the only time I wished someone had been there with me. 

After these blessed few miles, I arrived at Salta Verde Point, and the coast opened up to my left.  I knew from studying the map that if I stuck to the coast, I would add several miles to the paddle, so I pointed my nose straight to the farthest thing I could see, which was Church Rock, and a landmark for my left turn back to the leeward side of the island. 

This portion of the paddle would be a long straight paddle, far from shore.  It was probably 5 or 6 miles to Church Rock, and from there, it would be another 4 miles to Avalon harbor.  I decided at this point that taking my mind off the monotonous pain of repetitive motion would be a good idea, so I put in headphones and listened to an audiobook about never quitting.   

By the time I hit Church Rock, I was tired.  I had now gone about 14 miles, and I had four to go.  But now I was heading back to the lee side, and I figured that the wind and current would be against me.   I was going to have to dig deep at this point, so I sat on my board to fuel up and rest for a bit before I started this last leg.  I set my paddle down, and laid down.  I let my muscles relax and closed my eyes as the board floated next to Church Rock. 

When I opened my eyes a moment later, I realized I was moving at a pretty solid clip, and to my complete surprise, I was moving toward Avalon.  This meant that the same western swell that had propelled me down the island most of the day, was now whipping around the end of the island toward Avalon.  This was a most unexpected gift from Poseidon!

Now completely stoked, I shot up and started paddling hard to get the most I could out of this lucky stroke.  I was flying down the coast, past huge numbers of pelicans resting on shore rocks, past Seal Rock, not so aptly named because about 100 sea lions (not seals) were piled all around it.  I hugged the coastline, now with the mainland on my right, with an idiotic grin on my face.  It was the home stretch.

The current eventually reversed itself as I got near Avalon, but at this point, I didn’t care.  I passed the mine, the sewage treatment plant, the helicopter pad and the Buffalo Nickel restaurant.  When I got to Pebble Beach, and I was paddling only about 10 feet off shore, a tourist truck stopped on the road, and the driver pointed me out to the tourists as if I was a stop on her tour, and asked me where I was coming from through her loudspeaker.  The tourists took my picture as I waved and the truck puttered on. 

Just as I entered Lover’s Cove, close to 1pm, where the glass bottomed boats roam, I got a group text from several of my paddle buddies who had been paddling in Santa Rosa with me one week before.

“Are you dead?”

I replied, “I made it and I feel like a bad mofo.”

The reply: “You are a bad mofo.” 

An hour later I was sitting in the jacuzzi at the Island Spa after a massage.  I felt like I was two inches taller, and a million dollars richer.  I felt like Brad Pitt walking around with Stephen Hawking’s brain and Bill Gates’ money.  I had conquered the island, and my own fears, and a sense of triumph infused me.

Even Bill Gates couldn’t buy that feeling.  You cannot purchase, borrow, or manufacture that distinct and powerful impression of accomplishment.  It can only be earned.  And once earned, unlike a lot of other things in life, it can never be taken from you.  It goes on the CV forever:

– Whooped Some Ass (Santa Catalina Island, 2019)

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