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The inaugural Kaaboo Cayman festival had the potential to be another Fyre fest. Promised acts included the Chainsmokers, Flo Rida and Salt-N-Pepa; Bryan Adams and Duran Duran; Zedd and Blondie; the comedic stylings of Wanda Sykes and Kevin Nealon; cooking demos by chefs such as Michael Mina and Richard Blais, and food and drinks galore amid a picture-perfect Grand Cayman setting. Guess what? It was incredible! – and there wasn’t a cheese sandwich in sight. We took the opportunity to ask some of the performers – all of whom are frequent fliers – for their best travel tips. Herewith, their answers.


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As an ex-military man, musician Shaggy says 'if you’re on time, you’re late.'Randy Shropshire/Getty Images

The Jamaican musician and former U.S. Marine just wrapped up an extended tour with Sting and is back at it again with solo dates in Canada and Britain. He’s usually on the road 300 days a year.

What’s always in your suitcase? “A set of toiletries built for that suitcase alone: Toothpaste, toothbrush, deodorant, hair products, lotion, my shavers.”

What about bling? “Back in our day it was called bling, but now it’s called drip. My son just taught me that. When I’m on vacation with the family, it’s just a watch, but showbiz is different because I like how the light hits it and it’s part of the show.”

Any hotel preferences? “Boutique hotels are always my favourites. The little one-offs with character. I’m a different beast though because I live on tour, so hotels are my home. I argue over two things: My first-class seat and my room. I don’t stand up for much else, but my first-class seat has to be there or I’m not moving.”

Room service? “I don’t like food in my room. And they always screw it up.”

Are you a spa man? “I check them out at almost every hotel I’m in. I probably go three or four times a week when on tour. I like the spa area experience: Letting the toxins out in the steam room and the pool. I also get a few massages a week – deep-tissue or aromatherapy.”

Do you enjoy a hotel bar? “Every evening during our last tour, Sting and I would go to the hotel bar after the show and have a glass of wine if there wasn’t Monkey 47 gin. Otherwise we’d have a gin and tonic. That was our routine. One gin, or one glass of wine and great conversation.”

Are you usually early or late for a flight? “I’m an ex-military man, so I’m never late and I don’t like people who are. My thing is: If you’re on time, you’re late.”

Best packing tip? “It’ll take me four hours to put my stuff together. I get an itinerary of the tour, how many shows, what countries, and I look online to see what the weather is during those days … it’s a process.”

Kevin Nealon:

The American comedian and actor was a cast member on Saturday Night Live for almost a decade, but more recently has starred in Weeds and is currently in the sitcom Man with a Plan. He also tours regularly for stand-up gigs.

Best part of travel? “Getting there. But I try to make my travel as easy as possible. I join the airline clubs. I have global entry so I can get through TSA quicker. I have a gold car membership so the car is ready for me when I arrive.”

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Actor and comedian Kevin Nealon suggests keeping all your stuff in one area so you don't forget anything.Alberto E. Rodriguez/Getty Images

Best travel tip? “The most luxurious thing I do is there’s a company called the Private Suite at LAX. It’s designed to be paparazzi-proof. We don’t do it all the time, it’s expensive [around $1,500 a trip] and it’s a membership thing. You don’t go in the main terminal, you go to this little place and you have your own suite with food and drinks, a TV and a couch. Whether you’re leaving or coming, they drive you straight to the plane and walk you up to the gate. And they meet you when you come back and there’s a private customs person who checks all of your stuff.”

Mini-bar hacks? “I try not to hit the mini bar because it’s overpriced, and if my wife gets in there – she wasn’t raised like I was, and she has no problem taking out a Diet Coke and drinking it. I don’t do this any more, but I used to go out and buy one to replace it.”

What is always in your suitcase? “I have to decide between three things when I travel [owing to carry-on space restraints]: Bringing my banjo, my computer or my golf clubs. So I usually just bring my computer.”

Beach, ski or cultural vacation? “I like a beach vacation because it’s not a lot of work as opposed to a ski vacation, which is a lot of packing. But it’s a little more exhilarating than lying on the beach. It depends on what I’m in the mood for.”

Best packing tip? “Keep all your stuff in one area in your hotel room so you don’t forget anything.”

Salt (of Salt-N-Pepa):

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Cheryl Renee James, aka Salt of Salt-N-Pepa, says less is more when it comes to packing.Gregg DeGuire/Getty Images

Now 32 years into the biz, the awesome hip-hop duo is currently on tour with the New Kids on the Block, Tiffany, Debbie Gibson and others – for the Mixtape 80s Baby Tour.

Best part of travel? “Fabulous hotels. I like boutique hotels. In Cayman I’m in the Kimpton, and I love Kimptons all over the world. I also really enjoy villas, where you have that home feel and a kitchen and you can buy your own food and have parties with the crew."

What do you want in a hotel room? “It has to be a suite, the bedding has to be incredibly soft and inviting. I like minimalist, simple clean lines. And I love a big shower. Champagne on ice waiting for me is also nice. And the fruit and cheese plate welcoming us. Sometimes I look forward to the cheese more than the Champagne!”

Worst part of travel? “Oh, I can talk a lot about that. The airplanes, the up and down, a double flight, I hate that. Packing and unpacking. I’m a last-minute packer; I just can’t get it together. Packing for 32 years is the worst, most depressing part of the job. I feel like I’m always sitting on the floor in front of the suitcase, either taking something out or putting something back in.”

Best travel tip? “Less is more when you’re packing. You’re not going to wear everything you’ve packed and a lighter bag makes travel a lot easier. And pack the night before, even though I don’t do it.”

Chef Richard Blais:

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Chef Richard Blais says some of the best parts about travel are 'getting to see new ingredients, making new friends and learning about different cultures.'Daniel Zuchnik/Getty Images

Newly buff with a healthier lifestyle, the Food Network star travels market-to-market doing 75 to 100 big-name cooking demos a year. He calls it “Stand-Up Cooking” – somewhere between cooking, comedy and magic.

Favourite travel snacks? “I’m on a weird diet right now where I’m not doing any sugar or flour. It’s a lot of raw fruit and vegetables, natural nut butters and hard-boiled eggs, which is always weird on a plane.”

Mini-bar go-to? “It’s always fun to use your coffee machine with a bouillon cube. You’re always just a step away from hot soup! I also love room-service cheeseburgers.”

How do you pack special equipment? “For this show we probably had 40 per cent of what our equipment usually looks like. I like to travel with a flame-thrower – but we didn’t want to risk it. I’ve had nitrogen tanks confiscated, like the one I just used to make an instant rum granite during a cooking demo, but this one was borrowed from the local Ritz-Carlton.

Window or aisle? “I prefer the window because I love taking photos from the windows on airplanes, which is a running Instagram feed in my stories.”

What is always in your suitcase? “There’s always a weird vintage spoon, some sort of tweezers and an offset spatula. Plus some sort of weird fitness apparatus, like a lacrosse stick or a ball. With lacrosse all you need is a ball.”

Best travel tip? “If you have a morning flight, bring a truffle to shave over your omelette. Then you’re the guy shaving a truffle over your powdered-egg omelette and it’s a good story for whoever is sitting next to you."

Best part of travel? “Getting to see new ingredients, making new friends and learning about different cultures. Food and culture are so connected. So the more people you meet and the more places you go can really bring people together.”

Chef Michelle Bernstein:

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Chef Michelle Bernstein recommends drinking 'a ton' of water not eating a lot of airplane food when flying.Bennett Raglin/Getty Images

The celebrated Miami chef just opened Café La Trova in the city’s Little Havana, a Cuban bar and restaurant with live music, harking back to pre-Castro Cuba (circa 1950s). She also just finished filming Moveable Feast for PBS, travelling in the Caribbean and Mexico, as well as a PBS documentary on the Florida Keys.

Do you research restaurants before you travel? “My restaurants are chosen at least a month before I even book a flight. I ask friends first. I ask chefs I kind of know second. Then I start researching online and I look at cookbooks I either have or borrow, by chefs who have restaurants. I don’t look at Yelp. Recently, what I’ve found useful is googling where chefs like to eat in certain cities. We’re all in articles on where we like to eat in our home towns.”

Travel snacks? “I’m all about fruit. So I always try to bring as much fruit as I can, and if I can’t [because of cross-border fruit issues], I try to make little sandwiches for my young son and husband. Prosciutto and Manchego cheese, which holds up really well, egg salad with a touch of Roquefort cheese, and sandwiches de migo – like Argentinean tea sandwiches.”

Do you pick up food souvenirs? “Always. Right now I have two bottles of Cayman hot sauce in my pocket. There are two souvenirs I always take home: One is a food souvenir and the other is a spoon. I usually ask before I take them – I just love spoons.”

Best packing tip? “Because I work in a kitchen I don’t like to smell like a kitchen. So before I pack I spread all of my clothes out on the bed and I spray them with my orange-blossom perfume [by Marc Jacobs]. You smell like you and you don’t have to pack the perfume.”

No. 1 travel tip? “Drink a ton of water and don’t eat a lot of plane food. You lose 30 per cent of your palate up in the air so there’s a huge amount of sodium – 30 per cent extra – in the food to compensate.”

The writer travelled as a guest of the Cayman Islands Department of Tourism. It did not review or approve this article.

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