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

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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.

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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.

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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.

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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.”

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Happy Sailing

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// Jake

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