Key West- From an Insider’s Perspective


Tyler Knight grew up in Key West. Now at 24-years old, he could be considered an expert. Though he’s
not sure how much longer he’ll stay (“It’s hard to meet girls here”), for now he’s straight from Central
Casting with his surfer looks and demeanor.

Tyler, who also served in the Coast Guard, works for the top beach rental company on Key West,
“Barefoot Billy’s,” which offers about a dozen options on the water and land. We met Tyler during a
sunset cruise of 16 people on a pontoon boat full of drinks and expensive food. Our friends said it was
the best of the three Key West sunset cruises they’ve experienced.

The next morning, it was coincidentally Tyler again who was our tour guide on a guided jet ski loop of
the key. He knew all the nooks and crannies.

Ray and Tyler Knight

Ray: Is this what you pictured yourself doing when you grew up here?

Tyler: I’ve always been working on the water. I taught people how to swim at a young age, I was a
competitive swimmer all around Florida, so being on the water all day is second nature.

Ray: What do you like most about your job?

Tyler: Meeting all the people that come around. Meeting new cultures, new people—it’s very diverse.
Ray: What’s the biggest mistake you see vacationers make in your city?

Tyler: They party too hard. “Come on vacation, leave on probation.” Not good.

Ray: You’re out in the sun all day, every day. Have you ever been to a dermatologist?

Tyler: (Laughs.) I have not yet. I’m trying to save up money for that. I know my skin is pretty fair.

Sometimes I’m tan, other times I’m fried and I can’t sleep.

Ray: What are the best kept secrets of Key West?

Tyler: Night-time kayaking.

Ray and Erin

Ray: How about socially?

Tyler: I’d say check out places beyond Duval Street. (200 bars in one mile.) There’s Whitehead Street
and other roads that run parallel that people don’t see. Those backroads have great bars as well.
People tend to focus on Duval—you know, Sloppy Joe’s and Irish Kevin’s, but some of the best finds
are away from the area’s closest to the center of town.

Ray: Did you see the Netflix series set in the Keys called “Bloodlines”?

Tyler: Yes. My buddy was an extra in that. I saw Vince Vaughn here last year filming (an upcoming
streaming series called) “Bad Monkey.” I was 6 feet away from him. He was in the zone, pacing back
and forth.

Ray: Have you ever seen Jimmy Buffet walking around here?

Tyler: Yeah, you see him walking around. He keeps incognito. I’ve seen Kenny Chesney. He has a
place here.

Ray: In closing do you like how Key West has evolved since you were a kid here?

Jimmy Buffet’s Recording Studio

Tyler: I’ve seen a lot of change…a lot of things come and go. No need to rush around town, that’s the
whole point of it. Island time.

For more information on renting anything from jeeps to bikes to boats to jet skis, go to