Long Haul Club: Sailor to Seafarer

Every passage comes with its ups and downs—like a bipolar rollercoaster designed by Poseidon himself—but that’s the nature of crossing open water. Each one is unique, each one is humbling. And yet, no matter how high the wind or the seas get, the amount of inevitable repairs, squalls or insomnia that occurs between departure and landfall, there’s nothing like the feeling of getting this little boat through another big stretch of ocean. Because truthfully it’s the issues that make the trip. Persevering overhand overcoming the odds. Don’t get me wrong—I love a calm night with a sunset to rival all sunsets turning into a billion stars overhead, the smell of the sea, the breeze on my face, the sound of the water washing across the hull—perfection.

Pro Tip: Buy “Jimmy Cornell, World Cruising Routes” and  “Nigel Calder, Boatowners Mechanical and Electrical Manual.”  They are both invaluable tools to an offshore sailor. They are both available paper back or kindle.  Personally I have paperback of both for obvious reasons (lose power they are useless).

Pacific Ocean Crossing

3,170 miles — 3.5.22 – 3.25.22 (20 days)

La Cruz, Mexico ➝ Nuku Hiva, French Polynesia

Logistics (Field Guide):

Motor the first eight hours out to clear Banderas Bay — it’s tight, gusty, and not worth flogging into submission just to say you “sailed the whole way.” The trades begin to fill southwest of the Socorros; head south early, before the equator, to set up a friendlier wind angle later. This isn’t a dead-downwind sleigh ride but a S–SSW dance, so trim for comfort and let the wind decide the rhythm.

Expect 18–25 knots and 2–3 m seas at 8–15 seconds with scattered squalls. Don’t be afraid to motor through parts of the ITCZ if needed. Obviously, use your own judgment based on your diesel usage, amount of fuel onboard, and whether you need diesel for charging. If your forecast only calls for a day of calm, maybe ride it out sailing and flogging — for me, it’s not worth the punishment past that. I have an engine for a reason. Saying “I didn’t turn on my engine” means nothing to me; safety, not beating up my rig, and frankly comfort are more important. If your thinking about impressing people down the line you probably should not have left in the first place. The ocean will punish hubris. Regardless once you clear it ITCZ south the trades will fill back in and it will be smooth sailing all the way to Polynesia.

Captain’s Log:

Crossing the Pacific was my baptism by fire and salt — the moment the training wheels came off and Poseidon handed me the keys to the deep end. Three thousand miles of blue infinity, wind in the 20s, rigging humming like an electric guitar solo. Days melted together: water, sky, repeat, until I couldn’t tell where one ended and the other began.

Halfway through, a davit snapped and my dinghy went rogue, surfing behind the boat like it had joined the circus. There I was — half-asleep, headlamp blazing, lashing chaos together with adrenaline and zip ties, laughing because this was exactly what I’d signed up for. Nights so still the stars doubled in the sea until it felt like I was sailing through space; mornings where the sun burst from the horizon like it was auditioning for the role of God.

By day twelve I stopped fighting the ocean and started dancing with her. Navigation became faith — trust the wind, trust the boat, trust the stubborn fool on board. When Nuku Hiva rose from the haze, it wasn’t landfall; it was graduation day. I’d entered as a sailor. I came out a seafarer — tired, sun-streaked, and grinning like I’d just pulled a fast one on the universe.

The Singapore Strait

48 miles — 12.23.23 (1 day)

Batam, Indonesia ➝ Puteri Harbour, Malaysia

Logistics (Field Guide):

Leave Batam at first light — you want every ounce of daylight for this run. Cross the lanes at a clean 90° to minimize your exposure and keep your course intentions obvious. AIS is non-negotiable. Singapore VTS monitors Channel 14 and Channel 16 simultaneously; they’ll hail if you drift or dither. Respond fast and clear — hesitation looks like incompetence.

Use the designated corridors, track CPA/TCPA religiously, and motor hard. This is not the time to “see how she sails.” Stay on the Malaysian side of the line when rounding; Singaporean waters mean paperwork, police, and polite but time-consuming hassle. Expect heavy lightning at night — keep radar rolling even on clear evenings because haze can erase the world in minutes.

Captain’s Log:

Crossing the Singapore Strait was like playing Frogger on hard mode — except the cars are 1,000-foot tankers doing twenty knots, and you’re a tiny fiberglass frog powered by caffeine and prayer. From Batam to Puteri Harbour was 48 miles of pure adrenaline: cargo ships looming like skyscrapers on the move, tugs dragging barges the size of neighborhoods, and every blip on AIS a potential story ending in a courtroom.

The air smelled of diesel and thunder; the sky blinked like a disco run by angry gods. At one point I threaded between two tankers so close I could read the rust patterns on their hulls and wave at the watch officers who definitely weren’t watching. It was chaos, but magnificent chaos — the kind that sharpens you into a blade. By the time I tied up in Puteri Harbour, I was wired, soaked, and smiling like I’d just gotten away with something glorious.

The Malacca Strait

323 miles — 10.22.24 – 10.23.24 (2 days)

Puteri Harbour, Malaysia ➝ Pangkor, Malaysia

Logistics (Field Guide):

Northbound, track just outside the shipping lane — safe from the gear fields to the east and the steel stampede to the west. Southbound, steer clear of the Indonesian side: it’s shallower, snaggier, and not especially friendly. When you meet oncoming traffic, fall off 35° to starboard, let them blast by, and slip back into line.

Tugs and flatbeds often run unlit and radio-silent, dragging barges that could eat a sloop for lunch. Tankers turning toward Malaysian ports will slow or veer suddenly — six miles of crossing zone means an hour of white-knuckle watching. Big ships to port broadcast bright and true; local fishers to starboard may appear out of nowhere, grinning into the dark. Lightning is a nightly light show during inter-monsoon months — keep radar spinning and coffee flowing.

Captain’s Log:

The Malacca Strait was Singapore’s angrier cousin on a two-day bender — a never-ending parade of steel, nets, and neon madness. Three hundred miles of dodging unlit barges, sidestepping floating debris, and squinting at thousands of green fishing lights that turned the horizon into a Martian rave. It was so busy the ocean actually felt crowded, like sailing through a city that never sleeps and never signals.

Tugs charged by like freight trains on meth, and I was the kid on a skateboard in the middle of the tracks. Sleep was theoretical; caffeine was religion. Yet somewhere in that neon chaos, a strange joy took over — the thrill of staying just barely ahead of disaster. When Pangkor’s shoreline finally appeared, the world went quiet. The AIS cleared, the sea went still, and I laughed out loud — because in the Malacca Strait, peace isn’t given. You earn it.

Indian Ocean Crossing

2,675 miles — 7.10.24 – 7.30.24 (20 days)

Cocos Keeling ➝ Port Louis, Mauritius

Logistics (Field Guide):

The Indian Ocean doesn’t do favors. Weather systems roll through every 7–10 days with 4–5 days of heavy southerly blows in between. Depart Cocos Keeling on the back side of a system and aim about 15° south of the rhumb line — it’ll let the storms hit from astern instead of the beam. When they pass, curve north toward Mauritius and avoid Chagos altogether.

Expect wild wind variation: 15 gusting 30, 20 gusting 40 — and squalls that double the forecast in seconds. Reef early, shake out late, and make peace with never being perfectly trimmed. Seas are a confused mess of three swells fighting for dominance; flat sailing is a myth here. Shipping lanes are miles north and south — you’ll see no one. For 14 days, I didn’t see a single mast, hull, or soul. Bring every spare part, mental reserve, and drop of patience you own.

Rig a drogue or warp lines before departure; don’t wait until you’re already airborne. And test your setup beforehand — the middle of the Indian is no classroom.

Captain’s Log:

The Indian Ocean was twenty days of wet boot camp run by Poseidon himself — a symphony of screaming wind and waves taller than ambition. Every hour was a test: jib halyard gone rogue, sail flogging into the sea, me climbing the mast mid-storm like a caffeinated monkey clinging to a lightning rod. The boat pitched and rolled like a drunk trying to stand on a barstool in an earthquake.

Somewhere around day eight, a ghost net wrapped the prop. Midnight. No moon. Just black water and my reflection in it. I dove with a knife and a headlamp, cutting it loose while the hull heaved like an angry whale. When I climbed back aboard, I laughed — not from courage, but from disbelief that I was still here.

Then the leak started. Slow, sinister, steady. I mopped for days and prayed the hull held. Orcas showed up near the end — ghostly shapes sliding through gray water like gods checking their handiwork. By the time Mauritius rose through the haze, I was a patchwork of salt, caffeine, and stubbornness. The Indian didn’t beat me. She baptized me.

The Mozambique Channel

1,612 miles — 10.12.24 – 10.28.24 (16 days)

Crater Bay, Madagascar ➝ Baie de Baly, Madagascar ➝ Linga Linga, Mozambique ➝ Richards Bay, South Africa

Logistics (Field Guide):

The Mozambique Channel is chaos wearing a current. Eddies spin like drunk whirlpools — some rocket you ahead at 4 knots, others stop you dead or throw you backward. Plot your route between them using current charts; there’s no middle ground here.

Expect to stop at Linga Linga or Bazaruto to wait out weather — they’re shelter, not customs ports, so stay discreet. The southern half of the channel is where the real trouble lives. Northerlies can flip into southerly gales overnight, colliding with the Agulhas current to form short, vertical seas that can break ships in half. Never sail south if a front’s coming — those who do become stories other sailors whisper.

Keep warp lines or a drogue ready before you leave; don’t improvise when the sky turns feral. If your dinghy’s still in the davits, forget the drogue — the lines are your best hope. Richards Bay is the first real safety net, and the welcome there feels like a rescue.

Captain’s Log:

The Mozambique Channel was a knife fight in a washing machine — wind screaming, seas standing, and me somewhere in between laughing at my own audacity. Leaving Madagascar, I threaded between eddies like dodging invisible tornadoes, trying to ride the right swirl and avoid the wrong one.

I ducked into Linga Linga to hide from weather, skipped formal check-ins, and prayed to every maritime god I could name. When I finally set off again, I caught a northerly that betrayed me faster than a bad ex. Within 24 hours the ocean lost her mind — 50 knots, 20-foot breaking seas, lightning so close it was like paparazzi for my last moments.

The dinghy was in the davits, so the drogue was out of the question. I streamed two 400-foot warp lines like tails on a comet and hung on. Even bare-poled we surfed at twelve knots, the boat roaring down waves like she’d found religion. If I’d been caught inside the Agulhas, I wouldn’t be here to tell you this. But somehow, morning came. The sea went gray and soft. And when I limped into Richards Bay, soaked, shaking, and alive, the dock cheers sounded like a standing ovation.

The Wild Coast and The Cape of Good Hope

1,120 miles — 11.7.24 – 11.18.24 (11 days)

Richards Bay, SA ➝ Durban, SA ➝ East London, SA ➝ Cape Town, SA

Logistics (Field Guide):

From Richards Bay to Cape Town, every sailor earns their stripes — or loses them. The Agulhas current runs southwest at up to six knots. Add a southerly wind and you’ve got an instant demolition derby of vertical, breaking seas. Never chase comfort here; chase timing. Move in short coastal hops, waiting for a clear 3–4-day window of northerlies or calm.

Forecasts are wishful thinking; the Wild Coast writes its own weather. Have bailout ports ready: Durban, East London, Port Elizabeth, Mossel Bay, Simon’s Town. Each offers a place to regroup before the next round. Durban’s for repairs, East London’s for coffee and warmth, Mossel Bay and Simon’s Town are where you stage your assault on the Cape itself.

The Cape of Good Hope earns its name only if you’re lucky. Round in daylight, with a westerly or soft northwesterly if you can, and never trust a forecast under 20 knots — those katabatic winds hit like sucker punches. Once you reach Cape Town, tie down everything. The wind there has a PhD in chaos.

Captain’s Log:

The South African coast was a gauntlet in technicolor — beauty with brass knuckles. Leaving Richards Bay, I felt like I’d just escaped one boss fight only to walk into the next level. Forecasts meant nothing. Squalls appeared from nowhere. The Agulhas current twisted under me like a live wire, and the boat would suddenly leap forward as if hitched to a runaway train.

Durban offered a breather and the best warning of my trip: “Don’t walk outside the marina at night.” Naturally, I did. East London gave me hot coffee, laughter, and the warmth of locals who’d seen too many sailors crawl in wide-eyed. Then came the Cape — that mountain with teeth. The sea went flat, the wind went calm, and then, without warning, the world exploded. Katabatics hit like slaps from a god who disapproved of your haircut.

But I rounded her. Twenty-two weeks from Indonesia, 5,500 miles, one entire continent later — bundled in every layer I owned, grinning like an idiot. Cape Town greeted me with gales, dock lines snapping like bullwhips, a five-year sobriety milestone, and a tattoo to mark the moment. Africa didn’t offer comfort, but she gave me proof — that I could take the long way, face the worst she had, and still smile into the wind.

Atlantic Crossing — Part One

1,953 miles — 1.3.25 – 1.16.25 (13 days)

Cape Town, South Africa ➝ Jamestown, St. Helena

Logistics (Field Guide):

This leg across the South Atlantic is the ocean’s apology for everything that came before. From Cape Town, steer northwest to clear the coastal currents and Namibian wind shadows before bending toward St. Helena. Expect gentle SE trades of 8–15 knots and long, even swells.

It’s the perfect stretch to experiment with twin headsails or wing-on-wing setups — “Simbo style” transforms the boat into a balanced glider. Reef early, relax late, and watch the miles melt away. Traffic is minimal; hazards nearly nonexistent. Keep clear of the Benguela Current near the coast and expect a few calm patches near the subtropical ridge. Approach St. Helena in daylight; moorings only, no anchoring.

Captain’s Log:

After the Southern Ocean’s chaos, the South Atlantic felt like the ocean finally gave me a wink and said, “My bad.” Ten knots of breeze, swells like breathing, and for once — blessed silence. I rigged twin headsails, poles out like wings on a lazy albatross, and Hold Fast just flew. The sails whispered instead of screamed, the wake sighed instead of hissed, and I remembered what peace at sea feels like.

For thirteen days the world was blue and endless and merciful. No squalls, no gear failures, not even an argument from the autopilot. It was less a passage than a floating meditation — just me, the boat, and the quiet heartbeat of the trade winds. When St. Helena rose through the haze, I laughed out loud. The ocean that once tried to kill me had just tucked me in instead.

Atlantic Crossing — Part Two

2,036 miles — 1.29.25 – 2.11.25 (14 days)

Jamestown, St. Helena ➝ Recife, Brazil

Logistics (Field Guide):

From St. Helena, steer northwest, letting the southeast trades carry you toward Brazil. Stay west of the Mid-Atlantic Ridge to dodge light air and eddies. Expect 12–15 knot SE breezes and rolling following seas — mostly a broad reach or comfortable reach the whole way.

Squalls are mild compared to the Pacific or Indian Ocean, but the heat builds as you close the coast. Alternate between sail and motor in lulls; wing-on-wing setups shine here. Keep watch for FADs and unlit fishing boats within 200 miles of Recife. Aim for a daylight arrival — the harbor’s busy but straightforward.

Captain’s Log:

From St. Helena to Brazil was a joyride on autopilot — the ocean finally on my side, the wind steady, and the sky too lazy to throw a tantrum. I set the sails, poured coffee, and watched the world turn from cobalt to tropical teal. The trades hummed, the rigging sang, and the only real challenge was remembering what day it was.

Every sunset looked Photoshopped, every night sky a planetarium built just for me. The logbook barely changed: 12 knots of wind, smooth seas, still alive. After months of chaos, the simplicity was intoxicating. When Recife’s skyline shimmered out of the haze, I almost didn’t want the ride to end. The ocean and I were finally on speaking terms — and for once, she wasn’t yelling.

Atlantic Crossing — Part Three

2,587 miles — 4.11.25 – 4.26.25 (15 days)

Recife, Brazil ➝ Le Marin, Martinique

Logistics (Field Guide):

From Recife, head northwest to cross the equator between 25°W and 30°W, where the ITCZ is usually narrowest. Stay west of the Mid-Atlantic Ridge to avoid weak patches. Once north of the line, the NE trades fill steady at 15–20 knots for the final reach into the Caribbean.

Expect light winds and heavy squalls in the ITCZ — radar is your best friend. Motor through the calms; patience won’t move the boat. Reef early, shake out late, and keep decks clear for 180° wind flips in squalls. Optional pit stops include Îles du Salut (Devil’s Island), Suriname, or Grenada — each offering a sanity break before the last leg north.

Captain’s Log:

Crossing from Brazil to Martinique was like sailing through a mood-swing in slow motion. One minute the sea was a mirror, the next it was a riot of lightning and sideways rain. The ITCZ doesn’t care about your plans — it’s like sailing through the emotional life of Poseidon himself.

I burned diesel when the breeze ghosted off, reefed down hard when it came screaming back, and laughed somewhere in between. The sunsets were molten gold, the nights pure electricity, and every squall felt personal — like the sky was testing if I’d learned anything. By the time I hit the NE trades, I was sunburned, soaked, and blissed out. When Martinique finally appeared, it wasn’t relief I felt — it was gratitude. The Atlantic didn’t hand it to me easy, but she handed it to me true.

The Caribbean Sea

1,232 miles — 6.8.25 - 6.17.25 (9 days)

San Juan, Puerto Rico ➝ Colón, Panama

Logistics (Field Guide):

Westbound across the Caribbean is no pleasure cruise — strong easterlies of 25–35 knots (40+ in squalls) and short, stacked seas (6–10 ft at 5–7 seconds) keep you honest. Route 40–60 miles offshore to skirt the worst of Colombia’s coastal acceleration zone.

Expect organized squall trains, relentless lightning, and zero rest. Reef early, double-lash everything, and clip in. Jamaica’s Montego Bay and Port Royal make good midpoints; Santa Marta or Cartagena offer proper marinas before the final stretch. The San Blas Islands (Guna Yala) are the prize before Colón — calm anchorages, surreal beauty, and a brief chance to remember why you do this. Shelter Bay Marina inside the breakwater marks both finish line and portal to the Panama Canal.

Captain’s Log: 

The Caribbean run from Puerto Rico to Panama was eight straight days of beautiful hell — a blender full of lightning, wind, and bad ideas served with a side of humility. The trades screamed in the mid-30s, squalls marched like armies, and sleep was just a rumor. Both headsails shredded early; the Hydrovane choked on seagrass; the alternator quit, leaving me serenaded by the world’s angriest generator.

Then the prop fouled. Twelve-foot seas. Midnight. Knife between my teeth. I dove, swearing at Neptune and my own stupidity. Cut it loose, climbed back aboard, and started laughing — because sometimes the only sane reaction to chaos is joy.

Lightning lit the ocean like a rave hosted by Zeus, and warp lines streamed behind Hold Fast like comet tails to keep her steady. When I finally crawled into Shelter Bay, she was battered but proud, and I was salt-streaked, wired, and alive. The Caribbean hadn’t beaten me — she’d thrown every punch she had, and I was still smiling through the spray.

Final Thoughts: The Ocean Doesn’t Care Who You Think You Are

The ocean does not reward hubris. She’s a patient teacher, but her lessons are rarely gentle. Ego will get you thumped — hard. Out here, confidence is earned, not declared. You can have the best gear, the latest forecasts, and a thousand miles under your keel, but if you stop respecting her, she’ll remind you who’s in charge.

Check your weather, and check it again. Then have someone else check it to make sure you didn’t let optimism do the math. Redundancy isn’t overkill; it’s survival. Every spare part, every backup system, every “just in case” plan you make on land is what keeps you alive when things go sideways at sea.

Because passages aren’t really about perfection — they’re about preparation, patience, and adaptability. You can’t control the ocean, but you can control your readiness. And when the wind howls, the waves build, and the sky disappears, that’s when you find out who you are. Not the sailor you wish you were — but the one who holds fast, checks the rig, and keeps moving forward anyway.