Catalina, You Beautiful Troublemaker

A Love Letter to Two Harbors

Land Ho!

That speck on the horizon? Catalina. More specifically, Two Harbors—the Isthmus. Avalon is for the city folk with their golf carts and beach cabanas. Give me the quiet side every time. The Isthmus is my Shangri-La: peace, salt air, and a mooring ball that rocks me better than any therapist’s couch. After weeks tied to docks in Panama and L.A., I felt dock-locked. Brian belongs on the swing, in an anchorage, with the ocean beneath me.

Nostalgia, Saturated

Catalina in spring is like Ireland with better tacos. The hills glow a cartoon-green, as if someone cranked up the saturation just to mess with me. Every corner whispers, remember that time… followed by either a grin or a wince. Catalina has been my home away from home—months and months of my life spent here, logging soaring highs, crushing lows, and every flavor of lesson in between. Loved and lost, laughed and cried, and maybe even sobered up a little.Actually, not “a little.” Catalina is where my sobriety began. Five years later, 2,044 days sober, I can honestly say this island changed my life as much as any ocean passage.

A Top Five Forever

Forty thousand miles, 125 anchorages, mooring fields, and remote villages later, Catalina still sits firmly in my top five. And that’s not just nostalgia talking—it’s genuinely one of the best. Perfectly situated, perfectly scaled: quiet, relaxed, stunning. The hiking trails snake up into wide views, the snorkeling is alive with color, the fishing still fills the cooler, and the people? Always ready to trade a story or a Buffalo Milk (the island’s signature drink) at the bar.Avalon has its parades and its chaos, but Two Harbors? Two Harbors is a gift—nature’s porch swing right off L.A.

Hidden Hammocks & Secret Caves

One of my favorite Catalina treasures is Hidden Hammocks. It’s a decent hike, rewarded by a bluff shaded with slung hammocks and a waterproof bucket filled with journals. Over the years, travelers have filled the pages with poems, sketches, stories, and the occasional love note. Sometimes I’d read for hours, letting other people’s adventures tangle with mine. If you go, bring a pen, an old journal, maybe even a hammock of your own to add to the mix.And then there are the caves—perfect for exploring by dinghy. Just don’t forget to plug the dinghy (ask me how I know). Between snorkeling runs, Cherry Cove concerts, and impromptu cliff dives off my buddy’s six-deck sportfisher/trawler/thingamajigger, Catalina never stops dealing in both wonder and slapstick.

Firsts, Lasts, and Everything Between

Catalina was the backdrop to so many of my firsts aboard: first solo anchoring, first late-night barbecue, first lesson that a taco tastes better after a long swim. It will also be the setting for my last night of this circumnavigation. Come 2026, Hold Fast will end her first lap around the world swinging peacefully in this mooring field, closing the circle where it all began.

Why Catalina?

Because it’s perfectly set up to relax right off L.A. You can leave the chaos of the city in the rearview and, in just a few hours, drop into a world of hiking trails, hammocks, Buffalo Milk, snorkeling, Bucaneer Days, and sunsets that convince you the gods still paint with a heavy brush.Catalina, you beautiful troublemaker—thank you for being the place I loved and lost, the place I discovered new friends, the place I began again. Try not to get too wild without me.

Until next time.