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On the Wind Sailing

Troy Sears // Schooner AMERICA

On the Wind Sailing

Andy Schell

Sports, Wilderness, Places & Travel, Society & Culture

4.8593 Ratings

🗓️ 17 February 2026

⏱️ 85 minutes

🧾️ Download transcript

Summary

Troy Sears is the owner and captain of the San Diego-based Schooner AMERICA, a 144-ft replica of the racing ship that came to be the namesake of the famous Cup. Troy is a huge America's Cup nerd & history buff, delving into the history of the Cup and starting the podcast off with a question about the origins of the word 'yacht.' Troy lives aboard AMERICA with his dog and captain's the boat on daily whalewatching trips 330 days per year. We talked about how he came to buy the boat, his career sailing AMERICA all over the oceans, running the chase boat for actual America's Cup campaigns and much much more in an exciting, unexpected, and wide-ranging interview.

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Support the podcast & become a member of The Quarterdeck, where Andy, August & Mia dive deep on the art of seam'nship. Nerd out with us on our members-only forum and talk boats, gear, safety-at-sea, meet like-minded sailors, find crew, and more. Check it out on quarterdeck.59-north.com. See you there!

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This season of ON THE WIND is supported by our friends at Offshore Passage Opportunities and Rutgerson Marin. Support the show by supporting our sponsors!

Transcript

Click on a timestamp to play from that location

0:00.0

We never talked about this, but in terms of like people I've taken out. You know, Arnold Schwarzenegger, heads of state, countries, you know, all this kind of stuff. And I'm like going, and it wasn't in a big group. It was just his family. Wow. You know, and it was like. Wait, did they just come out as public people or as private?

0:21.2

Was it a charter?

0:38.0

No, he was so cool. So you're talking about Arnold. Yeah, he was so cool. No, it was his, you know, he has people. Yeah, I don't have people. He's got people. And he's like, well, his people are like, yeah, we're coming out. And he was governor at the time. and I go like, I'd be happy to host them.

0:39.0

No, no, no.

0:37.6

He insists on paying whatever he would would whatever someone would

0:43.9

normally pay to do yeah yeah I'm like okay well he was the governor when he came on the boat yeah

0:48.2

that's a really cool and and um it was him his wife and, and his children, period.

0:55.0

He has security detail.

0:56.7

He didn't want his security detail on the boat, so he put him on another boat.

1:00.8

And they just trail it.

1:02.4

It's like, you wouldn't even know that was his security detail.

1:05.1

Interesting.

1:05.9

Wow.

1:07.0

So.

1:07.1

He just wanted the privacy or be with the family?

1:08.7

Yeah, he just wanted family time.

1:10.3

And he's also the only person who asked me to dock, can I dock the boat? And I said, yeah, okay. Wow. You know, I mean, you wouldn't, you know, the Coast Guard would freak out on me. You let the person dock the boat and then you crash the boat. and that's why, you know, I don't know, I don't know.

1:31.3

You know, he's a, you let the person dock the boat and then you crash the boat and that's why he'll go

1:27.5

I don't know he's a very intimidating guy he's ever did he do it yeah hell yeah

1:36.2

on the wind is presented this season by two old friends of the podcast rutkerson marine a hardware

1:42.3

company in sweden close to home for me, and OPO,

1:46.0

offshore passage opportunities run by our good friend Hank Schmidt, fan of the podcast, friend of

...

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