MAKING FRIENDS AT SEA

2026-2 | FALKEN | Cabo San Lucas-Costa Rica
Passage Blog
Wednesday, February 11, 2026

01:59 UTC | 12°59.243’N 093°00.673’W

Sailing

Apprentice Jake here. It’s been about a week since writing about sipping morning coffee and hearing about Robert’s wild stories working at the surf shop, and a lot has changed over the last days on the high seas. The first couple days were easy, breezy, fun-filled days getting to know everyone. I never would have expected everyone to form such tight bonds so fast.

I am absolutely loving the Woodwind x 59º North mash-up. A lot of the time on Woodwind, the guests will ask about what it’s like to work on a boat, and of course it’s amazing! I wanted to work on the Woodwind to hone my sailing skills. The unexpected bonus was how much I’ve enjoyed getting to know the guests on the boat. We get everyone under the sun on the boat, and everyone has a story to share, and I eat it up. The only downside is when they have to get off the boat and we’ve only scratched the surface of each other’s story. I tell the guests that while I love the Woodwind, I want to try longer charters so that I can get to know the guests on a deeper level. I had a feeling more time with guests would be more rewarding, and I could not have been more right. It’s been nine days at sea with only one person that I knew before getting on Falken, and it feels like I’ve known everyone for years.

The first couple days, while everyone was getting to know each other, it felt very similar to working on the Woodwind, with great, mostly surface-level conversation. I hope the crew doesn’t mind me speaking for them, but right around day four it felt like the offshore switch was turned on and everyone stopped caring about superficial landlubber things like wearing clean clothes or brushing your hair. There’s something about seeing someone moments after they wake up, with sleep in their eyes and wild hair, that allows you to freely open up to those around you.

During one of our regularly scheduled afternoon watches, I was chatting with the crew about life and how this trip has filled holes of camaraderie that have been vacant for years. My regular spiel about my time traveling around the states in my camper van came up, and something about Offshore Jake came into play. After hundreds of iterations of the story being told on Woodwind, I was remembering aspects of the story that would be inappropriate to bring up on a two-hour day cruise but are completely welcomed by new family. As I start my offshore career, it has driven home the importance of sharing your adventures with people because, as Capt. Delaney always says, “joy shared is double joy.”

Happy Sailing

// Jake

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A last hurrah

Under the dome of stars in a moon-less sky, each of us during our time at the helm used the most rudimentary celestial navigation, keeping a star or two lined up with the mast as a helper to following the heading range. It was a whole crew event to set the spinnaker, reef the mainsail and practice the heave-to in case of man overboard. Alex stressed that the key to success in all of these crucial activities is preparation. It was hugely satisfying to accomplish these tasks through teamwork. We share a constant good hearted back and forth full of stories, one-liners and comebacks that also means constant laughter.

11/9/2026
A last hurrah

One little bird!

Falken has almost rounded the Channel Islands and is cruising along splendidly about 100 miles offshore. Though several models predicted some slightly fresher winds today, we were met with a consistent 18-20 kts of pure bliss. It seems that from the moment we left the dock in San Francisco, there has been much laughter and conversation amongst everyone. The plan is to gybe in a few hours and begin our approach to Ensenada. As much as I do appreciate the jokes and intellectual musings, I equally appreciate the natural, silent moments we share at night, all of us on watch gazing up above to the shooting stars, constellations, and planets putting on their quiet show.

10/9/2026
One little bird!

Birds and glows

The sun brought new wind and we were soon putting up the Yankee (jib) and turning off the motor. During the evening tradition of sharing “glums and glows” that follows the crew dinner, our Mate Ryan proclaimed it a “champagne sailing” kind of day. As Alex noted this evening, life goes by so fast that one of the very best things about his line of work is enjoying the passage of time in the slow lane of an ocean passage. But by tomorrow, the green blobs in the weather sailing app indicate we’re going to pick up some significant northwesterly winds and we’ll take them ever further south to the Channel Islands latitude. We’re all super excited for the knots to climb and to see Falken really run.

9/9/2026
Birds and glows