One Distinguished Dude

Handel Whittaker’s whiskers, and his bar, are both well-known on Grand Cayman Island.

October 2, 2017
Handel Whittaker
One thing Handel Whittaker loves about owning his bar is getting to meet and converse with all kinds of people. Zach Stovall

“Can you handel this?” the T-shirt reads. Below is a photo of Handel Whittaker in his full-mustached glory. Whittaker is the owner of Calico Jack’s Bar and Grill on Grand Cayman’s Seven Mile Beach. And the shirt? His staff’s tribute to their beloved boss.

Handel Whittaker, Calico Jack's, Grand Cayman
We can’t imagine a better birthday surprise than this awesome T-shirt. Jon Whittle

Handel’s beach bar is a hot spot for locals, cruising enthusiasts and celebrities alike.“The island has approximately 65,000 to 69,000 people, and everyone knows about Calico Jack’s,” Handel says. People cruise in for the jerk chicken, Cay Brew and a rustic beach-bar atmosphere. Calico Jack’s might be most popular for its monthly full-moon beach parties. Handel, however, is most popular for his snazzy ’stache. “Here in Cayman,” he says, “if people don’t know my name, they always say ‘the guy with the big mustache.’”

What are some things you enjoy about your home?
Everything. The water, the people. They are honest, hard-working people — friendly. [And] the fish life: You have hundreds of fish with 200 feet of visibility. The fish life, the coral, it’s absolutely incredible.


Do people really come to see you for your mustache?
Every single day I get, you know, probably 10 [to] 15 people that [ask], “Can I take a picture with you? Can I take a picture with you?”

Why did you get into the restaurant/bar business?
I like to make people happy. I find the ­hospitality business so rewarding. I’ve met so many great ­people — doctors, senators, lawyers. I met the president, you know. I met Bill Clinton.

What would you say is special about Calico Jack’s?
You can sit on the upper deck and you are 40 feet from the ocean. You can take a dip. Leave your beer on the bar, go take a dip, walk up … and pick your beer back up.


What do you enjoy about owning a bar on Grand Cayman?
There are very few people who come in to work in the morning and look out and see that blue Caribbean Sea. You know, it is just incredible.

Calico Jack’s once hosted a Sports Illustrated photo shoot. One bartender claimed part of the bar as a memento.

Shallow sandbars in Grand Cayman’s North Sound bay house about 50 stingrays that guests can play with.


Swim with green sea turtles at the Cayman Turtle Centre. And view the predator tank, full of sharks and more.


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