How I Travel: Chelsea Handler Bought a First Class Flight with Babysitting Money as a Teen

Chelsea Handler taped her new Netflix comedy special Revolution, which premieres December 27, at the Ryman Auditorium in Nashville as part of a tour that had her perform over 100 shows criss-crossing the continent. “There are always the home-run cities, which are New York, Chicago, L.A., and San Francisco. But what's really been fun and surprising is the markets I'd never been to before: Birmingham, Alabama; Louisville, Kentucky; Omaha, Nebraska,” she says. “I thought, what is this going to be like?! But they ended up being some of the most awesome audiences. There is a pocket of my people everywhere, and they love it when you come to serve it up to them.”

In anticipation of Revolution’s release, Handler chatted with Condé Nast Traveler about her laser focus on riding first class, the drink she needs stocked in her hotel room, and her beloved second home of Whistler, Canada. 

What’s in her carry-on bag:

It's overstuffed. I have my iPad, my Bose headphones, my computer because I'm always writing a book or stand up. Then I have all of my makeup things and all of my medications that I can't lose, if for some reason my bag that I check gets lost. 

How she spends her flight time:

If I'm going to the east coast, west coast, or Europe I'll sleep. If it's less than four hours, I prefer to read. My last plane ride I read The Great Alone in one sitting, which was awesome. It's such a good feeling. That was 500 pages, and I had started it, but I read [almost] the entire book on the flight. That is my favorite way to spend a flight. Sometimes I watch movies, but I would prefer to get reading done.

Her go-to plane outfit:

I try to look respectable. I don't go to the airport in sweatpants or leggings, or anything like that. It's usually just a pair of jeans and a sweater [with] a T-shirt because I have a lot of temperature situations when I'm flying. I'm very temperamental. I run hot, so I always have a T-shirt on under everything in case I have to disrobe.

Her approach to vacations now:

I'm into being active on vacations. I'm over lying on the beach for seven days in a row. I can do that for two days, but probably not much longer. When I go to Spain, we bike all day long, we swim, we scuba dive, we hike. Constantly walking, constantly active. I think as you get older, you realize how important it is to be fit and strong. And my other passion vacation is skiing, which is where I am right now, at my place in Whistler, Canada.

How she makes herself at home on tour:

I travel with my assistant and a tour manager. And yes, I have things that I need to make myself happy, which are sparkling water and Diet Canada Dry Ginger Ale, which has to be everywhere I go. That is my favorite thing in the world. I don't know why everybody's not drinking it all the time. I have to have electrolytes all the time, obviously, because I'm constantly on planes. Then I have a grounding mat, so when I meditate, I ground myself. That's helpful with a lot of travel. I've learned over the years to pick up good habits, instead of bad ones. Usually by the end of the tour, it all devolves anyway, but you start out strong!

The first time she ever rode in first class:

I have a great story for that. The first time I ever flew, I was 10 years old. My mom took us from New Jersey to California to visit my grandparents. I had never been on an airplane before, and we walked past the first-class section and I was like, "Whoa, whoa, whoa. What's this? Who are these people?" My mom said, "Never mind that. We have six children. We'll never be able to afford first class. We sit in the back. Come with me." We go to the back of the plane. I'm like, "What? Speak for yourself! I'm definitely flying first."

So we got home from that trip, and I started my own babysitting company. When I was 10, I looked older, so I lied and said I was 15 and ended up babysitting for kids that were older than me. I had a regular 14-year-old client who I was constantly putting in timeouts. I saved up $3,500 with my babysitting empire. The next time I flew on a plane was three years later, when I was 13, and I went to a travel agent who lived on our street and bought myself a first-class ticket. The next time my family and I traveled to California, I stopped at 2A. I was with my two brothers and my mother, and I said, "I'll see you guys at the end of the flight." That was the first time I flew first class, and I've never flown coach since.

The best vacation she’s ever taken:

Bora Bora. I cried the day I left there. I couldn't believe how beautiful that place was. I'm sure it's got to be partly manmade because it was just too ridiculous. I couldn't believe it. Normally, I don't like that [beachy] stuff—I prefer culture and activity—but we were able to be active there. We went snorkeling for hours each day. My girlfriend and I took an edible once and went out snorkeling with this guy on a boat. He said we didn't come up for three hours. We were just so transfixed! And the ocean there, it bifurcates into all these different colors, from purple to lavender to blue. It's just so stunning. It's all volcanic rock. They pick you up from the airport in almost a gondola, a motorized gondola, to take you to the resort. I wrote the end of my last book, Life Will Be the Death of Me, there. We had a glass-bottom suite, and just spent all day in the water, every day. That was a pretty epic vacation.

How she judges a hotel:

The service, service, service. I judge a hotel by how quickly room service comes, and the presentation when room service comes. And not making it a 45-minute affair. That's a nice touch. I like everything professional and succinct.

The destination she could travel to a million times and not be sick of it:

Whistler, Canada. I spend as much time as I can skiing because I just love it. It’s the most satisfying way to spend your day: Ski for a couple of hours, grab a mid-morning margarita, get back out there, then go to après, and then you’re in home in bed by 7:30, 8:00 p.m. I realized during quarantine that I don't have a lot of passions like other people; I have three interests, and it's reading books, smoking weed, and skiing. I like the small-town vibe [of Whistler]. My family and I have spent eight or nine Christmases here; I've spent 9 or 10 birthdays here. I have a lot of friends here now. It's just my home away from home. I live in a little cabin, and I go and around town and do my own errands. It's my little big life.