Lanai’s Singing Cowboy – Jesse Taylor – Video

categories: USA Travel
Jesse Taylor - Cowboy and Future Country Western Music Star

Jesse Taylor – Cowboy and Future Country Western Music Star

During my stay at the Lana’i Four Seasons at Koele Lodge I had the opportunity to go for a horseback ride. I enjoyed the ride, my first, but had the bonus of meeting my guide Jesse Taylor.

As we rode along I learned that Jesse came from a town called Arlington in western Washington where his father was active in the rodeo circuit. Jesse can teach you to ride or even to rope. One guest was having problems trying to rope a practice cow. Jesse told him the trick was to trow the rope as you would throw a baseball. The laughter he received in response was because the guest was an MLB baseball player.

Lanai seems like an odd place to find a cowboy but this area has a ranching tradition that goes back more than 100 years. But for Jesse this is not just an unlikely place to meet his girlfriend from Buffalo, NY but also a stop along the way to his goal of country music stardom. At least until that dream pulls him back to the mainland, many days you can hear Jesse serenading the guests on the porch of the Lodge.

You can learn more about this “quintessential singing cowboy” and his music at Jesse was kind enough to give me permission to video one of his original songs:

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Chris Christensen

by Chris Christensen

Chris Christensen is the creator of the Amateur Traveler blog and podcast. He has been a travel creator since 2005 and has won awards including being named the "Best Independent Travel Journalist" by Travel+Leisure Magazine.

2 Responses to “Lanai’s Singing Cowboy – Jesse Taylor – Video”

Roxanne Darling


So, where was that MLB player you wrote about? This is yet another reason my sister Nancy really should visit. Her son (12th grade) is a rockstar baseball player in California and he would love to rub elbows I am sure.

Jesse has a nice voice – seems a bit too cheerful for those lyrics though!



I think the baseball player was the 1st baseman for the Cardinals but I am not positive. I suspect he is back home playing ball.

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