On the Road With Jason Heyward, Who Wants More Trips to Cabo and Fewer Trips to Cincinnati

Few people on earth travel as often as professional athletes. With On the Road, the GQ Sports Travel Questionnaire, they’re weighing in on everything from room service to flying comfortably to their favorite chain restaurants.

This is Jason Heyward’s 14th year playing Major League Baseball. That’s 14 years of boarding (private) planes basically every three days, constantly checking in and out of hotels, and spending summers shuttling between America’s major cities.

When he was with the Atlanta Braves, he became very familiar with the Southeast. His lone year in St. Louis gave way to seven with the Chicago Cubs, making him an expert on all things Midwest. Now playing his first year with the Los Angeles Dodgers, the 33-year-old is experiencing West Coast life for the first time. That endless jet setting has given Heyward ample time to think about packing strategies and the staples of a good hotel room—and to have witnessed some truly wild airplane behavior.

What are some essential items you have to bring with you when traveling?

I need to have some lotion. I need to have headphones for the music, and outside of that, I always have my iPad in my carry-on. I use that to watch video prepping for games. If it’s a long flight I’ll watch some shows or movies. The iPad is also good for FaceTime when I get to the hotel.

What are you watching right now?

My wife and I just finished Snowfall, which was dope. It was tough to see the ending of that. I just started The Diplomat randomly. What else? Mayor of Kingstown has been pretty good. I’m waiting on Yellowstone and 1923 to come back around, and Succession is a cool one.

Generally speaking, do you overpack or underpack?

Overpack, for sure. My wife always tells me that I got way too much stuff. But I err on the side of: you never know what you’re going to come across. You’re walking around and there’s bad weather, you sweat more than you thought you were going to, whatever. So I definitely have more shoes and shirts than I ever need. You don’t want to have to rely on other people, or rely on the ability to do laundry. I don’t want to figure that out! I’ll bring enough, and we’ll go from there. You have to be comfortable when you’re traveling. That’s what I’ve learned. Have what you need to have.

What makes a good hotel room and what makes a bad hotel room?

A good one just starts with feeling clean. Obviously, there’s some hotels that are older, but as long as they do a good job keeping it clean—sheets, towels, not dusty—then you can go in there and feel like you’re truly at home on the road.

A bad one is when not everything’s working in the room. If you have to go down to the front desk and tell them something doesn’t work—the phone, the TV, the lights, air conditioning—to me you gotta reset and change rooms. At the worst, change hotels completely, but I haven’t had to do that too often.

Do you have control over that? Even when you’re with a full baseball team, you can just dip?

You can still leave! I guess if you’ve played long enough, and know certain cities, you can choose to stay somewhere else, especially if the hotel’s not able to accommodate your people. It’s funny: in 2016 Dexter Fowler and I were staying at a Langham, but we were in villas. He and I both ended up changing rooms because of spiders. He changed hotels completely! It happens sometimes.

One very minor thing that I love in a hotel is when they give you the list of the TV channels so you don’t have to flip through and figure it out on your own, or find that one channel where the guide scrolls through very slowly.

Nah, that is helpful! You can turn the TV on right away and press a minimal amount of buttons. Because you’re only going to watch a certain amount of things, so if they make that easy, that’s great! On top of that, if you know what they do have and what they don’t have, you're not searching for something that doesn’t exist.

What’s your go-to room service order?

If I get breakfast: bacon, scrambled eggs, pancakes. Sometimes French toast. That’s my go-to.

What about chain restaurants? Do you ever just want something familiar?

For a while it was Ruth’s Chris. But fast food? Five Guys, easy. I like that it’s got that chargrilled flavor to it, I love the cajun fries, and obviously they’ve got the milkshakes. That’s everything you’d want in a burger joint. I like the vanilla or Oreo milkshake.

You’ve been to every major league city multiple times at this point. Give me an underrated road city and an overrated road city.

[long, contemplative pause] I feel like as a tourist, it’s hard to say D.C. is underrated. But the areas we used to stay in were, like, Arlington, [Virginia]. Then eventually we started staying near Georgetown. Over time, it went from being kind of a boring stay to, this is actually pretty cool! There’s some restaurants, there’s some classic vibes to it. But when I was starting out, I thought D.C. was kind of boring.

I’m tired of Cincinnati, Cleveland, and Milwaukee. But Milwaukee has Lake Michigan close by and I’ve seen it getting better downtown. Cincinnati and Cleveland are probably the toughest.

That feels like the least surprising answer here.

[laughing] It’s real.

Heyward shows frustration during a 2021 trip to Cincinnati

Chicago Cubs v Cincinnati Reds

Heyward shows frustration during a 2021 trip to Cincinnati
Jamie Sabau/Getty Images

What’s up with that haunted hotel in Milwaukee?

The Pfister? We actually just stayed there. I can’t say I’ve had any experiences with ghosts. The first couple times staying there, you do hear everything. I think it’s more just how the hotel is built. When you go out in the hallway or close a door—you can close it as gently as possible, it still slams. That’s my take on it. But other people have had stories where they felt like someone was pulling their leg, or they put their stuff on one side of the room and they wake up and it’s somewhere different. But I personally have not had any run-ins with ghosts.

Have you ever thought about cities you want the league to expand to?

I have thought about it. I think Nashville would be cool. I think, why not add another team in Texas? Austin. But getting outside of the country, why not go to, like, Cabo? Put a team somewhere tropical. Let’s take this to Brazil. That’s another culture that loves the sport. Obviously, that would suck for teams coming from really far away. But I feel like a lot of people would be really happy to spend a few days down there, experience a new culture, and play some baseball. They have these series in London. Next year the Dodgers are playing in Korea. Why not add something closer? It can break up the season a little bit, just give you something outside the country.

What’s your plane move?

It depends on the length of the flight. I do like to hang out with the guys and move around if it’s a longer flight. There are card games, but I’m not much of a card player. I don’t gamble much. But I do instigate! You have to. I’ll get some music going. Guys are having fun with their poker face. It’s fun to see who’s losing money and who’s gonna try to win their money back by the end of the trip.

You get to see who’s good at bluffing, calling, all that stuff. It’s good camaraderie. Then you get to also do the DJ shit when they’re not spinning it right. It’s something to do with the fellas, because especially on a night game schedule, there’s not as much time to hang out together. So the plane has a good vibe.

I know what you mean about the music. I’ve been in a lot of big league clubhouses when that pop country playlist comes on. It’s horrendous.

[laughing] I respect anyone who’s like, “Hey, I’m gonna change this. This is not it.” But there are days—like if a starting pitcher is going [and he’s controlling the music], we gotta let that ride. At least up to like, 20-30 minutes before game time. Then you can turn on some hip-hop or whatever.

Is there a dress code on the flights?

We wear team jumpsuits! That makes it very easy. We’ve got three jumpsuits we wear: a blue one, a gray one, and a black one. It really helps so much to only have to pack seven outfits for seven game days. On those travel days, we got the jumpsuit. It’s still kind of new to baseball, but I like it. You can still throw on some nice shoes with it or a hat to make it your own. On the road, there’s no true dress code, other than, “If you think you look good, rock it.” And don’t wear shorts.

Any traumatizing plane experiences?

Oh, plenty of those. There’s been some where we landed and thought the wing hit the ground. I swear! It’s traumatizing. We fly over water a lot, too. Chicago, coming back from the east, that’s always a knuckle puck. There’s been flights going into San Francisco where you hear guys yelling, “Pull up! Pull up!” because you’re going over the water and it looks like you won’t make it. Atlanta was probably the worst as far as weather and turbulence. We had to land in Tennessee one time. They’ll tell you when it’s bumpy, but it’s usually bumpier than they say it’s going to be. They don’t want people to freak out.

Where’s your favorite place you’ve vacationed?

Italy, by far. We stayed in Montalcino first, went to Florence for a couple days, then did Rome for like seven days. It was cool to see the different landscapes and three different cities. The food over there is amazing. Organic, real food, whatever you want to call it. Having that consistency on the daily, plus the people and the vibes, it made me appreciate Chicago even more. It’s similar [to Chicago] in the sense of—you can walk around and grab coffee. There’s hole in the wall spots, there’s really nice spots, you can take in the city without spending a lot of money. You can just sit by a river with a sandwich and a coffee. Enjoy a lake. Ride a bike.

Where’s somewhere you want to go but haven’t been yet?

Montenegro. That’s where my wife is from. We’re planning on doing that this offseason. But I would love to go to Africa. I’d love to go to Egypt and check out the pyramids and all that history we’ve read about and seen in the movies. I think that would be pretty cool.

What’s the strangest thing you’ve seen a teammate do on the plane?

This wasn’t a teammate. It was one of our postseason flights in Chicago. We were on a bigger plane because we had family on and it was an off day. There was one executive—I’m not going to say their name—but it was obvious they’d done this before. Newspaper, perfectly folded. On the takeoff, they used the newspaper as a surfboard and went from the front of the plane to the back of the plane, perfect style. Nailed it. You have to have a lot of practice to not fuck that up. That was the coolest, weirdest thing I’ve seen on a plane. It definitely kept the party going, because we were moving on to the next round.

Originally Appeared on GQ