At the finish line. Buccaneer Days in Catalina, after a five-hour crossing from Newport Beach.

The southern California waters from Mexico to Point Conception are generally safe and secure to navigate. But at the end of September, be on the lookout: buccaneers are known to frequent the waters off Catalina Island.

Though modern mariners have dismissed fears of privateering around the globe – outside perhaps the coast of Somalia – the Jolly Roger’s still flying high, and debauchery isn’t far behind. For the largest concentration of peg-legged, parrot-toting, patched-eyed scallywags this side of the Pacific bare down on Two Harbors, Catalina, for a daaarrrn good time.

Day 1: setting sail

With a deckhand by my side, a case of rum, some local charts, a handheld compass and rumors of a pirate hideaway, we start motoring north from Mission Bay, San Diego. My vessel is old but seaworthy. She’s seen many a similar undertaking in her day – more than myself in fact, with 10 years my senior. A stop on our journey is at the place of her origin: Newport Beach, CA. Costa Mesa, to be more exact.

Vessels during her era were made with inexact mix-ratios of hardener to resin. Designers often followed the rule, “more is better” creating heavy-duty glass hulls that were built Islander-tough. As we slowly travel north, a light sea-breeze prevents the Sorcerous from really flying her lines, but the new auxiliary diesel makes way on into the evening. We decide to stay the night in Oceanside, taking a coastwise route, and enter the harbor around 2200. A sea fog makes distinguishing the navigational aids tricky, but undaunted we follow the chart and reckon our position accurately. The fall Pacific glitters in the wake of my old boat as millions of microscopic organisms glow with the excitement of us passing by.

We find ourselves a slip on the transient dock, and head up to the dock master's office for registration. Oceanside harbor is a smaller harbor in relation to its coastal neighbors. The location also makes it difficult to enjoy the surrounding amenities without a stowaway bike or other transportation. We decide to relax on the boat, and head off early the next morning.

Day 2: Oceanside to Newport

The early morning conditions are perfect for fog, and as we leave the slip, a heavy cloud cover sits on our surroundings. We sound our horn according to the restricted visibility. The noise is the beat of our band with the motor holding tune, firing on all three cylinders through the mist.

A southwest swell built through the evening, and large swells roll the boat in predictable frequencies towards hungry surfers in local lineups. We’d appreciate those waves if time wasn’t a factor, which it unfortunately is; too often. From Oceanside we follow our bearing close, and quickly lose sight of land, probably somewhere off Camp Pendleton.

With fog like raindrops we make way, unable to distinguish sea from horizon. After a few hours to the tune of the diesel’s drum, the large point named after Henry Dana comes into sight. Boat traffic increase as we pass by the jetty entrance. Sportfishers skip by, leaving us in a distant wake. Around noon the wind finally picks up, blowing the fog away.

We raise the big Genoa, sheet in to a close reach and put the pedal to the metal, finally able to kill the motor, just sail. The silence is wonderful. Only the sound of waves lapping against the hull as that ancient method of propulsion carries us onwards.

We arrive in Newport Harbor a few hours before sunset. The plethora of activities and vessels are overwhelming, especially after a night in Oceanside. Newport Harbor is a boater’s paradise: tenders and sportboats zipping and ripping around the bays; ferries carry vehicles from island to peninsula and back; small vinyl-covered, retrofitted runabouts carrying retirees hither and thither with wine glasses in hand. The transient anchorage is centrally located in the backyard of million-dollar mansions; residences of those retirees making way with their Chardonnay, no doubt.

“One day,” I think to myself, as we set the hook and get ready for a night at the bars on the Peninsula.

Land ho: Newport Beach

It’s a well-known fact that Newport Beach is home to a thriving species of California cougar, and my first mate was on the hunt. Bar after bar we hop, like kelp paddies for yellowtail, until finally a strike!

I’ll spare the heavy details, but needless to say the evening was eventful. A weekend full of debauchery on the peninsula and its environs, local sailing with some old high school friends, a near fall from the deck while setting the asymmetrical off Crystal Cove, and a little beach break action off tower 2 made for an unforgettable couple of days in the harbor.

Back at sea – Newport to Catalina

With thunderstorms on the eastern horizon, I guess not all that atypical for Costa Mesa, and a small-craft advisory in effect, we head off on a 270-degree (per magnetic compass) bearing for the Isthmus at Catalina.

I remember that morning as if it was a dream. We set off before sunrise, hoping to arrive in time to enjoy a full day’s festivities. Just outside the breakwater, wind was blowing from the northwest – not quite gale force, but a single red pennant was warning mariners of the conditions off the coast. I make my way to the bow to handle some trivial task, and notice objects darting to and fro in sea bursts of lime-green effervescence. Lit pale green visible even a meter or so under the surface, they appear like comets shooting across an oily black sky.

With the main reefed, and a few spins of the furler to decrease some sail, we make our way into the day. The island in the distance slowly grows larger as we bear down on the destination.

Something not to forget while traversing the channel between San Clemente and Catalina Island: freighters! This deep-water channel is heavily trafficked by huge commercial freighters. A traffic scheme crosses longitudinally from San Pedro and Long Beach towards the big blue sea. Just a word of advice, five short blasts of the horn is a danger signal – it means move! Something I learned the hard way.

It takes around five hours to cross the channel, the wind howling from the northwest at gusts up to 30 knots. The sea's relatively small but white-capped in all directions. We cross the channel close-hauled the whole way, me trying my best to keep the boat on a steady plane, not using too much rudder. Gusts heave the boat over on her side, blue water spraying over the bow as each crest tries to push us back. Undaunted, we continue slicing through the surf like a hot knife through butter.

Safe harbor at Buccaneer Days

Then we arrive. Not at the island yet, but in the lee of her broad peaks.

The wind dies to a puff, waters turn turquoise, calm and inviting, and sirens sing their sweet song, luring us to the Two Harbors. Our course directs us south of the Isthmus, and from that approach all that's visible is a gigantic shit-stained white rock – a beacon to the entrance of safe harbor. As we motor north, the sirens show their true intentions, flying high hundreds of skulls and crossbones forebodingly grinning at our arrival.

I’ve been to the Isthmus numerous times in the past, but never have I seen the amount of vessels packed into those two harbors. Every square foot of water was overwhelmed with pirate ships! Raggedly attired, scantily clad, half-drunk buccaneers littered the landscape like trash in Tijuana. All moorings had long been claimed, but who wants to moor when anchoring is free?

We set the hook in the far southern cove of the southern harbor. It’s a perfect little anchorage, out of the way from all the sportboat traffic and relatively isolated.

The sea floor was heavy sand and held well in moderate conditions. We made it to the shore on my banana kayak, and quickly were engulfed in the scene. The desolate Isthmus awoke with a bandstand, vendors and thousands of drunken pirates – all much friendlier than those of days gone by.

Buccaneer Days is a sight to be seen, but even better to partake in. Next fall, when the Santa Ana's start blowing over the San Miguels, Zonies are back in their respected places, and the kids are finally fenced in at school, head out to the Isthmus. Be a pirate for the weekend. You’ll have a daaarrrnnn good time!!