San Diego to Cabo

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It’s been a while since we last published, and in that time we’ve sailed the entire length of the Baja peninsula from San Diego to Cabo, then rounded the cape back up into the Sea of Cortez. This post will cover our journey south, crossing from the US into Mexico and sailing down the Pacific coast of Baja.

After getting in from the Channel Islands (and having one of our most dramatic docking experiences yet, involving getting wedged sideways in our slip and Maddie needing to jump over a massive bull sea lion who was hogging the dock we were trying to tie to), we spent a week in San Diego prepping the boat for its next big passage and the arrival of our first-ever crew. This next leg of our journey would be as part of the Baja Ha-Ha, a longstanding rally of over 100 boats that sails from San Diego to Cabo each year.

This would actually be our second time on the Ha-Ha. We had originally planned on joining on our own boat last year, but when we decided we weren’t quite ready to leave the dock, we were lucky enough to get a spot crewing with Sally and Michael Aldridge on their boat Sweetheart. That crewing experience ended up being such a valuable way to build our confidence and gain mentorship that it really set us up for doing the much more challenging trek to Canada this Spring.

Although we had gone back and forth about whether we wanted to the Ha-Ha again, we ultimately decided it would be a welcome chance to meet other cruisers and hopefully set ourselves up to have more of a community down in Mexico. Given how much we had benefited from crewing on the Ha-Ha, we also wanted to pay that mentorship forward and—and all the better if we could get some new friends out of the experience.

But first, our time in San Diego provided a lovely chance to spend time with Maddie’s parents, Becky and Marty. They got an Airbnb in Mission Beach, walking distance from where we could anchor Tardigrade in the neighboring bay. It was a much-needed reset of hot showers, easy laundry, and use of a rental car for running our errands. It was also one of the longest unstructured periods we’ve had to spend with them as an adult couple. Even three years into being married, it has been interesting to still be experiencing new phases in the long process of integrating into each other’s families. On this trip Jeremy and Becky discovered an unexpected shared love of arcade games, we all shared a silly and memorable time surfing the beginner waves at Tourmaline, and we got to take notes on Marty’s exquisite fish grilling skills and participate in his newfound passion for long walks around town. And we continued to collectively learn to play pickleball together, however poorly.

Weaving our families into this sailing chapter has been generally difficult—being far from home and tricky to pin down on dates and locations has made it hard to have family visit, and not all of our loved ones are quite so eager to pack into a rolling boat or get blasted by wind and water as we are. Our time in San Diego was a rare chance when we had locked-down dates and location, and we’re super grateful for all the help that Maddie’s parents offered to ease the big transition.

Our desire to take on crew for the Ha-Ha was informed by wanting more social connection, as well as our growing awareness of how healthy it is for us to have a mission. Maddie and I both love to teach, and our own sailing journey was benefited so massively by the teaching experience we received while crewing for others that we were excited to pass it on.

Maddie found Chloe and Ryan more or less randomly while browsing a Facebook group of folks looking to crew around the world. They were British-born and living in Australia, seemed sunny and easy-going and interested in many of the things we loved (especially surfing). They had a little experience but were interested in trying cruising out to see if they might want to pursue it more seriously. They were outdoor educators and experienced travelers, and had spent lots of time sharing a small space living out of their van. On reflection, it felt like we barely did any due diligence other than noting those green flags and generally liking their vibe on the short phone calls we had with them beforehand. But luck was on our side, and the match ended up being better than we ever could have hoped.

We picked them up on the evening before the Ha-Ha got started in earnest.

From Jeremy’s journal:

Chloe and Ryan emanate warm excitement as we dinghy across the mirrored sunset water of the anchorage, and my subtle nerves that have pervaded the last few days of preparation start to dissolve away. Ryan is tan and clear-eyed and amicably gung-ho in a way that puts me at ease, Chloe is all smiles and freckles, unguarded and quick to hug. They’re immediately easy to like, and I have the feeling this is going to be a good fit.

As they climbed onto the boat and we took them through the abbreviated tour we had worked out, they nodded along gamely and were quick to ask questions. By the time we settled in to dinner on the first night, it seemed evident that we were going to get along well. By the time we were attending the Ha-Ha kickoff meeting the next day in full costume (a tribute to a cult classic sailing movie, Captain Ron), it was clear that the vibes were excellent. On the way back to the boat we happened across an abandoned surfboard on the dirt path beside the marina, which completed our quiver with one board per person. It seemed like a good omen for our shared adventure to come.

The start of the Baja Ha-Ha is quite a spectacle—some 130 boats all sailing out of the narrow entrance to the San Diego Bay together, honking air horns, captains and crew waving to each other in an air of general excitement. As we looked around at all these boats who were embarking on the start of the same dream, it was surprisingly touching to think back on this time exactly a year ago, when we were participating in this parade from the decks of Sweetheart. At the time we were awash in both the excitement of the moment and also sadness and a sense of failure to not be there on our own boat. But that delay had enabled us to do so much in the time since, making it possible to go north and prove ourselves in a much more substantial way than if we had rushed out the door a year ago. In that short time so much had changed about our skills and confidence that we felt totally at home in this parade, confident that the weeks ahead would be well within our abilities. As Maddie and I exchanged those reflections, we also soaked in the fun and cuteness of watching Chloe and Ryan bounding around the deck filled with awe of their own, ready to start their own journey.

The first leg of the Ha-Ha is the longest—three days and three nights during which you traverse roughly half of the total length of the peninsula. It’s also the only leg where it makes sense to go way offshore to catch wind, so it’s also the only window where you spend multiple days without seeing land at all. The wind built up over the course of the passage, so that what started as flopping sails and conditions so calm we were able to hop off the boat and take a bath in 10,000 feet of water eventually became a howling 30 knots behind us and seas so topsy-turvy that nobody got much sleep on the final night. Overall it was a near-perfect setup for introducing Chloe and Ryan to ocean sailing, and they rose to it incredibly well.

Our first blue day surrounded by the disc of the ocean in all directions, we sail on in easy rapport with Chloe and Ryan. In the satisfied lull after lunch Ryan asks aloud, “well what should we do now?” And a millisecond later the fishing rod on the starboard side screams to life. We shout in disbelief and excitement, laughing at the impossibly comedic timing as we scurry into action. I run forward and grab the rod, set the hook and feel the weight of the fish fighting me through the stretchy line. Maddie and Chloe furl the jib and start to head up while Ryan readies the net. The fight is much shorter this time than the albacore up in NorCal, the line is shorter and the weather milder, and I suspect from the resistance that the fish is smaller. For some spells the fish is swimming right at us and all I can do is crank as fast as possible to keep slack out of the line. All the extra hands help get the boat settled and by the time I see silver flash in the water and pull the tired fish alongside us, Ryan is dipping the net low and I easily hoist the wriggling bullet of iridescence into it.

I recognize this fish as the same beautiful striped variety that I first caught on the Haha last year, and our little ID guide pins it as a Skipjack. But we’re not about to waste our first fish, and in short order I am using the broad side of our mallet to club him while we hold his spasming body through the net. His death throes are fast and constant for a time, a furious staccato seizure that spatters droplets of blood from his dribbling chin, and I feel the rush of landing him darken with the murky guilt and sadness for destroying a beautiful thing.

Doing the Ha-Ha for the second time and on our own boat made it feel like more of a scaffold rather than a container. The places and schedule were familiar to us now and we felt more secure coming into anchorages in less than ideal conditions, freeing us up to prioritize sailing and not be stressed about timing. With our own little crew aboard, we also got to enjoy much of the friendship and relationship building we had hoped for without leaving the boat, making it easier to chart our own path and lead the way for others on the Ha-Ha.

The first place this became apparent was in Bahia Tortugas, the small fishing village that marks the end of the first leg. During our time here last year Jeremy had made some local connections who took him out surfing at a break a little ways up the coast, and this year we were excited to build on that groundwork and hopefully open up some opportunities for others. Unfortunately when we arrived we learned that all of Jeremy’s former connections had moved away, and we were back to square one. After spending much of the first afternoon in town asking around, Jeremy was connected to a young woman who could be our guide, and we were back on.

The next morning we flagged down a water taxi, whose captain was surprised but accommodating as we loaded him up with surfboards. We headed over to our boat neighbor Discovery to pick up Troy, a new friend who found us at the Ha-Ha BBQ and made us promise we’d include him in any surf plans. Then the panga dropped us at the rickety pier where we met our guide, Ale—a laid-back woman with skateboarder cool who lost no time strapping the boards to her jeep’s roof and installing Troy in the trunk.

We sped out of town and onto a rugged dirt road through the desert. Undeterred by a close call with a loose board almost falling off the roof (saved by grabbing its leash through the rear window), we finally pulled up to the remote stretch of beach framed by rugged cliffs and mesas. The only other people in sight were two friendly guys who’d road-tripped from LA in search of surf and spearfishing, and they welcomed us amicably and shared some fresh ceviche from the back of their truck.

We swapped waves between us for hours, reveling in having such a beautiful wave to ourselves and pulling it all together in spite of the setbacks. Surf exploration carries a unique joy for anyone who has done most of their surfing in crowded spots near cities: normally any spot that produces a quality wave will have at least a handful of others sharing it, and the surf culture of California is such that they’re usually quiet at best or actively territorial at worst. Having good waves all to yourself is glorious on its own, but being able to share that experience with friends who are brimming with stoke at having it for the first time is one of the most delightful rewards we have been able to cultivate in this sailing life so far.

After several hours of surfing we headed back just in time for the annual Ha-Ha baseball game, where the cruisers compete against local kids. We hung our wetsuits to drip-dry over the back wall of the bleachers, which we soon realized was inadvertently advertising our hookup to other would-be surfers in the fleet. In short order folks from other boats started approaching us hoping to join for round two. The next morning we piled nine people from four boats into two cars and set out for the break. This time the wave was even more clean and welcoming, and there was not a soul in sight. We had another glorious morning, full of party waves and everyone cheering each other on. Maddie alternated surfing with shooting photos from the cliffs, giving everyone plenty of souvenirs to remember it by. By the time everyone was cold or noodle-armed, we were glowing with accomplishment for helping so many people have such a cool experience.

On the second leg of the Ha-Ha we felt like we were hitting our stride as a crew. Chloe and Ryan had been learning fast and had accompanied us on overnight watches on the first leg, so were now ready to take on their first unsupervised watch. Adding a third party to the watch rotation greatly improved the amount of sleep we got each night, which added on to the already-substantial energy and time savings of having extra hands for all the cooking, cleaning, and sailing tasks. We passed easy days of calm sailing and growing comfort with each other as a little family on the water.

The afternoon passes lazily in gold and blue, the perfect disc of ocean and unbroken dome of sky seeming safe and close around our peaceful bobbing home. The wind and waves feel friendly and mild, just enough push to make good time without a hint of strain. We’re playing Catan, our little travel set laid out on a cutting board on Maddie’s knees while she sits in the companionway. Chloe and Ryan have picked it up quickly and Chloe has a commanding monopoly on a whole side of the hexagon. I’ve been boxed into a tiny corner after comically trading Maddie the wood she needed to block my one road out, but I’m having surprising luck with my little empire of wheat and my heart is quickening as I try to walk my wavering path to victory. Every now and again someone calls out “here fishy fishy!” to the fish that have been teasing us all day but never staying on the hook. The day passes like a warm nap in a breezy field.

Not long after, things went from 0 to 60 in an instant as three Mahi Mahi hit our lines within 30 seconds of each other. With everyone stretched thin in the resulting chaos, we lost two of them but wrestled the biggest one aboard and all fought together to keep it there.

In the first moment of silence since the boat erupted in chaos 5 minutes ago, we all sit in awed shock around the magnificent fish bleeding out on the deck. The Mahi is the most brilliant yellow I have ever seen on an animal, a 4 foot streak of fluorescent neon punctuated by shiny electric blue spots. His gills and jaw now a mangled mess of scarlet blood and tangled hand line, the gaff hook twisted awkwardly in sinew at his chin, a hole near his gills spurting blood onto the deck with each heart beat while the fish lies dazed and fading. I feel myself shaking with the adrenaline comedown. My hands are raw from holding desperately to his gill plates as we fought to keep the spasming fish on board, determined not to lose another like the others which just shook loose or flopped over. The air is still ringing with the aftertaste of commotion and thrill, all we can seem to say to each other now is iterations of “wow” and “look at that fish!” Slowly the background calm of sailing reasserts itself, and we set about our work to clean the fish before dark.

Ryan and I lay back against the deck in the vanishing dusk, the last of the massive mahi steaks finally bagged away, our bodies aching with the dregs of exertion and adrenaline. Our budding routine of filleting fish on the rolling deck starting to feel like a meaningful shared space of friendship, a quiet and useful masculine act around a primal sense of providing. I reach up for a high five and our hands meet with a satisfying clasp and a comical squelch of fish slime.

We arrived at Bahia Santa Maria at the end of leg two at dawn with binoculars out, hoping to spot surf on our way in. This bay had been the site of our most epic surfing last year, and we were all chomping at the bit to get out there again. We anchored at the very edge of the fleet and rushed to put the boat away—sleep-deprived but running on stoke. We loaded our tiny dinghy with four people and four boards and puttered to the break.

The wave we encountered was a dreamy shoulder-high point break that wrapped around the entrance to the bay and broke in a peeling shoulder almost all the way to the beach. There wasn’t a soul in sight and the water was glassy calm in the early morning. We were hooting and laughing and could barely believe the conditions. It was one of the most delightful surf sessions any of us had ever had. After enjoying it for a while we offered to shuttle another group of surfers, and soon our whole nine-person group was out there making the most of it. It was the first of many sessions in the days to come, it was hard to get enough of having such a spectacular wave to ourselves.

Back from the party in the long light of the evening and what should by all rights be exhaustion turns to intrigue when Ryan notices surfers at the distant break. Zoe and Oliver have hitched a ride out for a sunset sesh and the waves look good rolling in around the point. I recognize in Ryan the same giddy longing and bottomless pit of surfing energy that’s brewing in me. We make quick eyes at each other, a cheeky volley of “you down?”s and we jump into motion, both seeming pleased to have a mission buddy as the girls retire for the evening. We jet out together and paddle in against the spray whipped up by the offshore wind. The waves are steeper and sucking shallow off the reef like they were last night. It takes a little hunting but I find myself a handful of fun waves with the coursing energy to make my carves and cutbacks feel like buttery heaven. I whoop into the glowing orange horizon as I step off the dregs of the last wave after riding it almost into the sand, turning to see Ryan close behind on one of the half dozen set waves rolling in through pink dusk.

One of the most painful parts of the Ha-Ha is the fast pace, which makes it hard to feel like you’re doing justice to any of the stops or the vast stretches of coastline in between. Having already been through the whole thing once, it had always been a vague option in our minds that this year we might decide to drop out of the fleet if an enticing opportunity arose. The surf at Bahia Santa Maria was quickly making the case for itself as just such an opportunity. We ran the idea past Chloe and Ryan, who were more than enthusiastic and purposely hadn’t arranged any travel plans just in case something like that came up. In short order, the decision was made. At the final Ha-Ha party that evening we gave our thanks to the rally organizers and said our goodbyes to the numerous friend boats we were already looking forward to running into somewhere down the line. The next morning at 6am, the fleet hauled anchor and left us behind.

Waking up to the foggy dawn and watching the haha fleet leaving the anchorage, cementing the fact that we’re dropping out and creating tendrils of giddiness and relief in my gut. Standing with Maddie as the last boats passed out, including a boisterous send off from Discovery, and appreciating how far we have come and how cool it is to have the freedom to be staying.

After the Haha fleet left, we stayed in Bahia Santa Maria for another four days, taking things slow. It was a lovely time in many ways and a transition back into the slow, unstructured lifestyle we had started to know over the summer in Canada. Even with the added social element of our crew, we still experienced some of the same melancholy that comes with moving out of a purpose-driven mission and into a more amorphous period with no defined goals. Both of us struggled with mental health lows and the incongruity of feeling sad or lost among so much freedom and beauty.

In response, we found lots of ways to keep ourselves busy. Between surf seshes Ryan passed on some of his spearfishing knowledge to Jeremy, and together they speared a handful of fish that helped stretch our provisions. We had been keeping a fish tally of all the fish caught on the trip so far, and as the tickmarks climbed into the double digits it was striking to realize how much of our food was coming from the ocean. This had a big impact on our ability to stay away from civilization for much longer than the two weeks we originally provisioned for. Even when the only veggie we had left was cabbage, we got creative making slaws and ate like royalty, feeling more connected to our food than ever.

Spending so long off grid was also a great test of our boat systems. We managed to meet almost all of our energy needs from solar and wind energy, which filled the big lithium batteries Maddie installed and allowed us to power the watermaker, a reverse-osmosis filter that turns seawater into fresh drinking water. With Starlink we were able to keep in touch with friends and family and have movie nights, and we tore through a series of gorgeous Torren Martin surf films that Chloe and Ryan introduced us to. Our lives were a curious blend of living off the land in the deep backcountry and living in the plush luxury of having your whole house with you at all times. Eventually though, the last of the vegetables ran out and the surf conditions deteriorated, and we prepared to head south.

We caught a perfect weather window which kept us sailing at full speed for the full overnight trip, and arrived into Cabo San Lucas with a mix of sadness to be re-entering the real world and excitement to taste vegetables other than cabbage again.

The juxtaposition upon entering Cabo was immediate and intense. As soon as you round the corner of the peninsula the massive sparkling hotels and sport fishing boats are everywhere. Further into the bay the anchored cruise ships loomed into view, surrounded by a steady parade of sailboats decorated like pirate ships out for booze cruises, glass-bottomed water taxis full of selfie-taking tourists, and the ever-present whine of roving jet skis. The beach was overflowing with big resorts blasting house music over the water from brightly lit sound stages.

Nevertheless, the bay was beautiful and the water was crystal clear and warmer than anything we had yet experienced. Once we dropped the anchor we lined up for a celebratory leap into the ocean and all came out hooting in delight at how pleasant it was. We could see easily 50+ feet down to the seafloor below us, and as we looked down we were surprised by a school of hundreds of mobula rays passing serenely below us. It felt like a clear juxtaposition of the two worlds we were bridging—the human chaos of Cabo built on and around the ongoing beauty and natural richness of Baja.

Over the next two days we did some much-needed provisioning, but it didn’t take long for us to start longing for quieter anchorages and head into the Sea of Cortez. Cabo had been our original planned point to part ways with Chloe and Ryan, but we had been enjoying having them so much that we invited them to stay on until Christmas, and they happily agreed.

Hosting them added such a fulfilling layer to the experience, one which both reminded us how much we enjoy teaching and provided an ever-expanding illustration of how much we’ve learned in our own journey. It has also had a lovely side effect and prompt return on investment in the form of having two ever-more competent extra hands on the boat, and getting to watch their interest in sailing bloom into a full-blown dream. As of this writing they are back home in Australia and actively looking to buy their own sailboat and start a cruising chapter of their own.

Hopefully we’ll be back soon with the stories and photos from that leg of the trip, heading north again from Cabo up to Loreto and exploring some of the best marine life and secluded anchorages that the Sea of Cortez has to offer.

Until next time,
Jeremy and Maddie (and Chloe and Ryan) (and Tardigrade)

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