Sailing South: The Stops That Shaped the Journey Through Mexico

Sometimes when you finally sit down with a cup of coffee and look back on a long journey, the memories don’t come back in order. They come back as moments—snapshots. A whale’s eye rising out of the ocean beside your boat. A harbor entrance that looks impossible until you commit and push the throttle forward. A tiny town where you break down, wait weeks for parts, and somehow end up meeting family you didn’t even know existed. That’s what sailing down the Pacific coast of Mexico was like for me.

It wasn’t just one trip either. It unfolded over years—different crews, different seasons, and a lot of learning along the way. Some places were magical. Others were frustrating. A few were downright terrifying. But each one became a turning point on the journey south.

Looking back now, there are five places in Mexico that really stand out. Not necessarily because they were perfect—but because they changed something about the voyage.

My trip south really started when I took my 1977 Formosa 51 across the border from Oxnard into Ensenada. Ensenada itself isn’t exactly the kind of place that ends up on postcards. But the entrance to the marina gave me my first real lesson about sailing Mexico.

There’s a tight dog-leg turn you have to make to get in. It’s one of those moments where hesitation will ruin you. If you creep in cautiously, you’ll drift off line and end up sideways in the channel. You have to commit. Throttle forward, turn hard, and trust the boat.

It became a bit of a theme for sailing Mexico: when in doubt, more throttle. A lot of the places along this coastline are like that. Charts are vague, entrances are shallow, and conditions change constantly. You quickly learn that indecision is worse than boldness.

If there’s one place that still leaves me speechless when I think about it, it’s Magdalena Bay. Mag Bay sits along the Pacific side of Baja California, and getting there isn’t easy. You either sail for weeks down the peninsula or fly into Loreto or Cabo and then drive hours across the desert to a tiny town called San Carlos. It feels remote because it is. But the reward is extraordinary.

Magdalena Bay is one of the few places in the world where gray whales come to calve. Between January and March, the lagoon fills with mothers and newborn calves. The wildest part is that they approach you.

You go out in small boats called pangas, heading toward the mouth of the bay. At first you see spouts in the distance. Then suddenly a whale surfaces right beside the boat. Sometimes the mothers lift their babies toward the surface, almost like they’re introducing them.

It’s hard to explain what that feels like. You’re looking at a creature the size of a bus, and it’s looking back at you. You can see the eye—huge and ancient—and you suddenly realize how small your boat really is.

For me, whales have always inspired a strange mix of awe and fear. I’ve had a few encounters offshore where one surfaced beside the boat, and when you see an eye that big staring up from under your hull, you start wondering where the rest of the animal is.

But Magdalena Bay somehow feels different. There’s a strange calm to it. After a day out with the whales, I always find myself quiet for a day or two afterward, just processing the experience.

It’s not just whales either. The bay is overflowing with life—billfish, oysters, clams, giant Pacific prawns. Fishermen haul in buckets of seafood that would cost a fortune anywhere else. And all of it is surrounded by desert. Dusty roads, tumbleweeds, and little taco stands that look straight out of a movie scene. Magdalena Bay feels like the edge of the world.

After Baja, I sailed south and eventually ended up in La Cruz, just outside Puerto Vallarta. This was a turning point for me.

Up until then, sailing had usually been a shared adventure. But when I arrived in Banderas Bay, I suddenly found myself alone on a very large boat.

Houdini is not designed for solo sailing. Nothing runs back to the cockpit, which means every sail change involves going forward on deck. The dinghy alone weighs enough to make you question your life choices when you’re hauling it up on a tired old winch.

But there I was. So I sailed. Around and around Banderas Bay, learning how to manage the boat by myself. Every maneuver was a small victory. Docking alone. Raising sail alone. Figuring out the rhythm of the boat without help.

And every so often someone would ask, “Where’s your crew?” When I told them I was alone, their reaction reminded me how unusual it was.

That realization brought a strange mix of pride and humility. Pride because I was doing it. Humility because I knew just how hard it actually was. La Cruz became the place where I proved to myself that I could handle the boat.

South of Puerto Vallarta lies a stretch of coastline called Costalegre—the Happy Coast. It’s known for surf towns, jungle scenery, and eco-tourism. On paper it sounds like paradise. For us, it became the place where everything broke.

We had just left Banderas Bay and were preparing to continue south when the problems started. The stuffing box began leaking. The raw water pump started acting up. Windows leaked. At one point it felt like the entire boat was hemorrhaging water. Our morale wasn’t far behind.

What was supposed to be a quick stop turned into a month of waiting for parts and trying to figure out which problems were dangerous and which could wait.

That’s one of the hardest parts of captaining a boat—making those decisions. When you’re responsible for everyone onboard, the line between caution and fear gets blurry.

We hired mechanics who sometimes knew less about the systems than we did. Parts arrived late or not at all. Eventually the part arrived and we managed to fix the problem and move forward.

But Costalegre also had its beautiful moments. One evening we randomly ran into Violet’s paternal grandfather on the street. He recognized her and suddenly we were invited to a massive family dinner.

Grandmothers, cousins, aunts—people we had never met before—welcomed us like we had always been part of the family. Moments like that remind you why Mexico captures people’s hearts so easily.

Oaxaca had been hyped in my mind for years. Handwoven textiles. Rich culture. Incredible food. Vibrant towns. But the coastline didn’t quite live up to the dream.

The region around Huatulco has nine bays, each with its own anchorage. We visited several of them hoping to find that perfect hidden gem. Instead we found rolling anchorages and scorching heat.

Night after night the boat rocked violently. Sleeping became a challenge. Even during the best cruising season, the heat was intense.

It made me realize something important: if you want to sail with family—especially small kids—you need at least one air-conditioned cabin. Some lessons come from beauty. Others come from sweat.

The last stop on my journey through Mexico was Chiapas. This place carried emotional weight.

Years earlier I had crossed the Bay of Tehuantepec while eight months pregnant. It was a reckless departure fueled by an argument and very little weather planning.

We ended up in a storm with 50-knot winds and opposing currents. For forty hours the boat barely made progress. The autopilot struggled. Waves slammed into us.

I remember putting my head down on the table at one point and thinking this might be it.

So sailing back through that same bay years later brought all those memories back. But this time was different.

We stayed close to shore, carefully choosing our route. The sea was calm—flat like a lake. The crossing that had once terrified me became peaceful.

That moment rebuilt something inside me. It proved that good decisions matter more than luck.

Even the final approach had its drama. Entering Marina Chiapas means navigating a winding channel through mangroves where everything looks the same.

At one point I turned toward a large ship thinking it marked deep water. Suddenly fishermen started shouting and waving their arms warning that it was dangerous.

I turned just as the keel skimmed the muddy bottom and followed their pointing until we reached deeper water. Mexican fishermen probably saved us that day.

Sailing down the Pacific coast of Mexico wasn’t a smooth journey. There were breakdowns, storms, sleepless nights, and a lot of uncertainty.

But there were also whales lifting their babies to the surface, unexpected family dinners, and quiet moments where confidence returned.

And the realization that sometimes the most meaningful parts of a journey are the places that challenged you the most, because those are the moments that change you.