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 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 only 16 people on a big pontoon boat full of drinks and expensive food.  Our friends said it was the best of the three cruises they had been on.

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—and rightfully so: He also served for the U.S. Coast Guard in Key West as well.

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: 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.

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?

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?

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.

Photos from Ray Collins

For more information on renting anything from jeeps to bikes to jet skis, go to Barefoot Billys.

Ray Collins says he’s helped his dermatologist put a new deck on his house.  Ray has been a travel writer since 2009.  www.raycollinsmedia.com/articles  He’s also an award-winning Realtor, media consultant, elected official and recovering TV newscaster.