Akin to traveling salesmen pushing knife sets or caffeine pumped truck drivers, skateboarders spend a lot of time in the air and on the road. It’s one of the beauties of the job, but it’s not always sunshine and roses.

Because there’s so much to know, I brought some of my burning questions up to skateboarding’s most traveled characters. Will Miles, Nestor Judkins, Patrik Wallner, Evan Smith and Anthony Claravell have spent more time traveling than 76.21% of skateboarding, so without further ado, here’s some tips, tricks and insane stories to keep in mind next time you’re stamping up that passport.

What’s one thing you should always AVOID doing when in a new city?
Don’t get involved in the weed finding mission on the first night, let them work it out themselves.

What’s one thing you should always DO when in a new city?
Find the local pool hall/shit bar that you’ll use for the one drink before bed or when it’s wet out.

How many pairs of underwear is necessary to bring on a five day trip? What about socks?
Even though I did shit myself in an airport I still would only bring 5 pairs of underwear. 10 pairs of socks though because you gotta change out of the skate socks when you’re done with the day.

“I managed to stop myself from puking, but in doing so I shit myself.”

What’s your wildest airport security story?
I was traveling to Mexico from LA and had gotten food poisoning from a burrito the day before. After being up all night throwing my guts up I went to the airport with nothing left in me thinking it might be safe. This was around the end of Covid so you had to wear a mask. I felt alright up until putting my bag through the security scanner. I was waiting for it on the other side and realized I was gonna puke into my mask. Luckily I managed to stop myself from puking, but in doing so I shit myself.

Give me three travel essentials and why each one is important to you?
Crocs. Once you start flying with crocs you can never go back. Noise Canceling headphones. They let you shut out everything, no crying kids, no airplane noise. I get more sleep on flights than at home. Spare shorts in your bag. Nothing better than changing into shorts mid-flight or on the layover. Feels like you’ve had a shower you definitely haven’t had.

Have you ever had a brush with death while traveling, and what happened?
I got in a taxi with a few of the guys in Cape Town to go for dinner and the guy driving was driving like a nutter, could barely make it over the top of some of the hills we were going up, fully rolling backward and stuff. He asked if any of us had any weed and when we said no he pulled a joint out of nowhere and told us to spark it up. He would sit still in traffic and let a massive gap open up between us and the car in front and then put his foot down as hard as he could and break suddenly when he caught up with the car.

He asked what we were doing that night and we said going for dinner and asked what he was gonna do, he replied “Probably smoke some crack and find someone to fuck in the back of the car” at which point everyone took a look at the joint they’d just smoked from him and got pretty worried. He took us through the longest route and I was pretty sure he actually ended up dropping us at the complete wrong place. When we got out I had to ask him for a receipt and whilst writing it he looked me dead in the eye and said “If you tell anyone about this I’ll fucking kill you.”

Three travel essentials?
Cameras and a notebook. Just two, I don’t have a third essential. Also memories to always remember and partake in where you are and who you are with.

Is there a strategy to having a good flight?
No, they always suck. Try to be exhausted but not hungover. Iron tablets help with restless legs. Aisle seat for me so I’m not trapped. Always change your clock to your destination right when you get on board. I actually really like long flights because as long as you’re on time, nothing is asked or expected of you but to just sit and watch movies and be quiet. It’s kinda liberating. Watch a cheesy movie and cry in a tin can 30,000 feet above the ground as we are all alone together.

What’s your wildest airport story?
I was in Madagascar with Patrik Wallner and the pilot of our flight came up to us hyped because his son skates. The country had so few skaters that he knew who we were. He invited us all up to the cockpit to hang out while he was flying. It was an old propeller plane and pretty rad old school travel experience that would never happen anywhere else anymore.

“Watch a cheesy movie and cry in a tin can 30,000 feet above the ground as we are all alone together.”

Have you ever been injured while far from home? What happened and what did you learn from the experience?
I spent five days in a hospital in London for an emergency lacerated / almost kidney removal. I learned that shit happens, that I strangely like to be forced to sit and rest when you have no other options and to succumb to the inevitable as long as it’s not permanent (kinda like I enjoy a long flight where there’s nothing expected of you but to just sit still). Also, always listen to your gut. I thought it was just a stomach ache as I was internally bleeding trying to eat Indian food during a team dinner before I decided to go to the hospital.

One thing to always AVOID when traveling?
“Chilling in the hotel”

What’s one thing you should always DO when in a new city?
Get on public transportation. Get on the metro, learn and explore. Go out and stay out as much as possible.

How many pairs of underwear is necessary to bring on a five day trip? What about socks?
Funny you ask about socks. I would say the more the merrier, since those low lying hotel beds can be a vortex or a dark hole for socks. While filming a skatumentary in Central Asia, I ran really low on socks and the crew was starting to complain.

I promised everyone once we reach the Gateway of Hell in Turkmenistan, I will dispose of my socks respectfully. However on that trip, we all got black listed to enter one of the last countries ruled by a strict authoritarian dictatorship since we were filming a documentary. But years later, on a solo trip using my Hungarian passport, I threw my socks into this pit of fire which has been burning for almost fifty years.

The last video I ever uploaded on my YouTube account before switching to Vimeo (terrible idea looking back at it now) was of this final promise to the crew. I forgot the password and my recovery email was an AOL account, so I never was able to delete this video haha.

Have you ever been injured while far from home? What happened and what did you learn from the experience?
I dislocated my right shoulder in Turkey badly. A friend popped it back and I was saved. A couple years later, when I was passing my heavy camera bag back to Jaakko Ojanen in a taxi in India because the driver couldn’t see his rear side mirror. It dislocated the same shoulder again but in a way in which it didn’t want to go back into place. It was 1AM in Bangalore on the side of a highway outside the airport laying on a sarong, while I was screaming in pain as Rob Wootton, Gaston Francisco and others tried to put my shoulder back in place. Had to go to the ER and wait for an hour for the specialist to arrive in pajamas.

“We kept writing notes to each other and ended up on a date the next day. Skateboarders will love this. I first took her to Flushing Meadows Park.”

Have you ever had an airport love connection?
Over a decade ago, I was flying with ANA (All Nippon Airways) back to New York and received a piece of chocolate from the stewardess. I was puzzled since no one else was getting a treat. I wrote her a note saying something like ‘Thank you and what’s your plans in the big apple?’ which I slipped into her hands when she came to collect the trash.

We kept writing notes to each other and ended up on a date the next day. Skateboarders will love this, since I first took her to Flushing Meadows Park to show her the globe, then we took the 7 train back to the city and showed her Tompkins Square park where we sat on the bench for ages and got harassed by a Russian speaking homeless man.

What’s one thing you wish you knew before traveling abroad?
It’s better to not act like an American who knows everything. Take the back seat approach and let life come to you sometimes. You might get robbed and kicked out of bars if your actions and words are speaking too loud. Fly low and slow under the radar. Save it for the session.

What’s one thing you should always AVOID doing when in a new city?
Keep your wallet in your front pocket. Watch your surroundings. Stay alert and safe. Don’t get to fucked up. This is applied while traveling alone. If you’re with a crew, watch out for each other. Remember people can be less fortunate than you at a certain point in their life. Stay humble. They might need what you have to survive.

“It’s better to not act like an American who knows everything. Take the back seat approach and let life come to you.”

What’s one thing you should always DO when in a new city?
When you’re in a new city, always get out there and experience the culture. Obviously be respectful, see the sites, skate-rat the plazas, make sure to reach out to locals and introduce yourself. Let them know where you come from and what you’re about. Take lots of pictures. Those memories are worth more than anything in this world.

Is there a strategy to having a good flight?
The key to having a good flight is to never check the time. You’ll get there when you get there. I like to have a couple airport beers before I get on the flight and relax into it. International flights usually have TVs. I wait to put the TV on until the first round of drinks comes around. Make sure to drink water when you get up to 30,000 feet. I never check a bag. It’s a waste of time. You should have all your essentials in one backpack and duct tape your extra boards to your board. Take your trucks off. Keep them in your backpack. This will get you around the planet.

Airport bars: avoid or indulge?
I would indulge in airport bars, but keep it tight. If you’re too drunk, they won’t let you on your flight. That goes back to the don’t say too much. Keep everything to yourself and fly under the radar. Also make sure you bring a hoodie, zip up is the best.

Have you ever been injured while far from home? What happened and what did you learn from the experience?
I have knocked myself out many times, this one was the worst. I was in Costa Rica doing a demo. I was with Cole Mathews and I woke up holding his hand in the van over and over and over my brain was reeling. I could become conscious for maybe 10 seconds and then it would go away, I was freaking out crying. I did not know what was happening. Eventually, my cognitive response had rebooted, and I had realized that I hit my head. What I learned from this experience is that life is extremely fleeting and in a second it can be washed away. Don’t take life for granted, I’m super grateful to even be telling these stories. And hopefully whoever is reading this can gain some sort of knowledge. Knowledge is power.

Give me three travel essentials and why each one is important to you?
Flip flops and swim trunks, you never know when you might be at a beach or pool or end up at a sketchy motel where you won’t want to be walking barefoot. Packable rain jacket, hoodie & beanie, lightweight and warm for either a sudden downpour or a freezing plane cabin. Battery packs, both a small one to charge your phone and a bigger one that could power a laptop or charge a camera.

What’s the best meal to eat pre-flight?
There is no science to it but McDonalds before a flight has happened many times across many continents. Ando Caulfield went from avoiding McDonalds for over a decade to indulging with me every time he flies out of Barcelona.

“Healthcare can be really cheap and accessible outside the United States. An emergency root canal cost me 20% in Spain of what it would be at home.”

Have you ever had a brush with death while traveling, and what happened?
No real brush with death, though I did get robbed at gunpoint with Frank Gerwer, Brian Uyeda, and Cairo Foster. Left the south of Taiwan one day before a major earthquake. No Final Destination type scenarios though, thank you very much!

Have you ever been injured while far from home? What happened and what did you learn from the experience?
Too many times to count. I’ve learned that healthcare can be really cheap and accessible outside the United States, something like getting stitches in Thailand, at a legit hospital with a course of antibiotics cost me $150 where it would be a grand in America. Same for a visit to the dentist and an emergency root canal cost me 20% in Spain of what it would be at home.

Have you ever had an airport love connection?
Not as many times as you would think, I do believe in minding your business on flights and I rarely initiate random conversations but one time I was flying from Poland to New York and sat next to two beautiful Polish women who were coming to the US for the first time on a work/study program. We had a great conversation the whole flight and I was going to get their info when we landed but then they got pulled into secondary and I never saw them again [laughs].

Interviews by: Ben Komins
Illustrations by: Jessi Knox
Share this with a vagabond Facebook
Report this as jetlagged Instagram and Twitter