While most of their time will be dedicated to practices and games, they will also try to utilize their time away from the rink as best they can.
"You're fairly busy on the road, so sometimes it's nice just to stay at the hotel and hang there, just take it easy," Sidney Crosby said. "Other times, depending on whether you have an off day or not, there's things you want to see. The bigger cities have more to do. We have guys that we played with before that are on different teams or guys that you know from your hometown, things like that, so you see them. There's always stuff to do depending on where you are."
When it's a short trip, guys tend to pack their bags right before they leave the house - or, as Bryan Rust admitted, sometimes he'll forget and have to go back home after practice before heading to the airport.
But when it's a long trip like this, the players dedicate more time and effort into packing than they usually do. The players' must-haves vary, from food to clothes to electronics. For Rust, he has to pack one bag of peanut M&M's for each game that he plays, a tradition that started back in high school when he played for the USNTDP.
"I have one bag every game day," he said.
Meanwhile, everyone knows which bag is Matt Cullen's due to the noises it makes.
"All the guys always laugh because my bag rattles with all the vitamins and stuff in there," he said. "Everywhere I move it rattles."
And of course, they all need to bring their passports along with suits, dress shirts and ties. Fortunately the weather looks to be relatively mild in western Canada, but it did snow in Calgary recently, so players plan on bringing winter coats and hats just in case.
While a lot of the players have been doing this for a while, that doesn't mean they've got packing down to a science. A few of the veterans said they tend to bring a lot more than they need.
"I'm probably guilty of overpacking a lot," Crosby said. "In case I spill something on my shirt, I don't want to be stuck with stains all over my shirt for the road trip. I'd rather have too much than too little."
The Pens will take six different flights on this trip - including two lengthy ones from Toronto to Calgary and then Vancouver to Pittsburgh - so they'll be spending a lot of time on the team plane.
Per the team dress code, the players have to wear their suits when they're heading to the plane. But once they get on, they're allowed to change if they so desire. Carl Hagelin is someone that tends to at least change out of his suit jacket and dress shirt no matter how short the flight is. And if it's a long one, he'll do a full outfit switch.
"Any time I travel it's important to bring a pair of shorts and a really comfy hoodie, so I can wear it on the plane but I can also wear it in my room on the road," he said. "You just try to be comfortable, I guess. That's the key."
This is a relatively recent development in Hagelin's career, starting in 2014 when his New York Rangers played the Los Angeles Kings in the Stanley Cup Final. And now that he's been part of two more Finals that have required a lot of cross-country flights, it's become routine.
"In New York I would never do that, then when we went to the Final and we had to fly for six hours to LA everyone changed," he said. "Ever since that, I was like, I should probably keep doing this. You don't have to change your pants every time, but for me, if it's over two hours you kind of have to do it."
Hagelin is one of the guys that likes to just relax and hang out while the team is flying. That group includes his seatmate Patric Hornqvist along with Crosby, Cullen, Jack Johnson, Matt Murray and Olli Maatta.
Crosby used to play the video game SOCOM on a PSP, but now he prefers to either sleep, watch a show, read a book or just chat.
"I don't even know if they make (SOCOM) anymore," he said. "Some other guys play Mario Kart. I tried, but I'm not very good at it. Sometimes it's just nice to relax, you know? Get that 45-minute nap in or whatever, just to hang out. Sometimes it's nice just to catch up with guys."
Crosby plans to start watching season 2 of Netflix's Ozark on this trip, while Murray and Johnson will also download movies or shows from the streaming service. "Way down in the cellars of Netflix, you can find a diamond in the rough," Murray said. "I just download as many as I can and if I don't like it I'll go to the next one." While they tend to keep it pretty chill, some of their teammates can't say the same.
Right in front of Crosby is the card table, where the loud and raucous games of 13-Up takes place. The foursome of Derick Brassard, Phil Kessel, Kris Letang and Evgeni Malkin play cards on every single flight, keeping score on a sheet of paper underneath their numbers. The deck of cards, paper and pen are set up and ready for them when they board the flight.
The games take forever, so they've come to an agreement that they don't have to end until they land back home in Pittsburgh, which allows them to pick up where they leave off on different flights. Sometimes they'll take breaks to nap, but those are few and far between.
"They're really intense," Letang admitted. "There's some people that play for a lot of money, but we don't even play for a lot of money. We just have fun with the game. We just hate to lose."
Brassard is the quietest of the four, while Malkin is the loudest. He, Letang and Kessel will literally be screaming at each other during games when they think someone's cheating, and sometimes they have to bring in neutral parties like Crosby or Hagelin to help settle disputes. Johnson learned the hard way just how loud that group is on his first road trip with the team.
"I have to make sure I bring headphones (this trip)," Johnson laughed.
The card game takes place towards the back of the plane, while the Mario Kart game takes place towards the front of the plane.
Rust said that former Penguin Derrick Pouliot was the one who first brought a Nintendo Switch on the plane, and it became such a hit that everybody else went out and bought them.
They have a core group that plays Mario Kart every flight: Rust, Brian Dumoulin, Jake Guentzel, Riley Sheahan and Justin Schultz. Conor Sheary was also a regular before he got traded to Buffalo. With him gone and Schultz out for four months following surgery to repair a fracture in his lower left leg, Rust said they're looking for new recruits.
When it comes to characters, Schultz is always Yoshi - "the red one," he said - while the rest of the guys tend to switch it up. Which is surprising, considering how superstitious hockey players are, but Guentzel said it's strategic for when they battle.
When they first started playing Mario Kart, they would just race each other. Then they began playing battle mode every once in a while, and Schultz said it was way more fun. Now they battle pretty much every time. Each driver has three balloons attached to the back of their carts, and if all three get popped, you're out. The last person left driving wins.
"It's pretty intense," Schultz said. "Guys get mad. You can be a little cheap in there. If you shoot one guy, some guys - I know I'm guilty of it - go after him right away again. That causes some mayhem."
Everyone agreed that Rust - who actually dressed as Yoshi for Halloween two years ago complete with three green balloons attached to the back of a scooter - is the best at Mario Kart. After that, it's a toss-up.
"I would say Rusty is the best. But it's crazy though, we'll all win games," Schultz said. "We didn't keep track last year, but I think we're going to this year. There's a way we can do it. You can look on there and see how many points everybody has. We should do it. It's a fresh start here, a new year."
While the games get competitive, Guentzel said they have a rule to keep any conflict from brewing.
"It's a lot of fun just yelling at each other, but our thing is what happens on the plane, we leave on the plane," he said. "Nothing leaves the plane even if you're mad at someone."
There's been talk of adding Mario Party into the rotation, and maybe even Super Smash Brothers. But for now, they're sticking with Mario Kart because they love it so much.
"On the plane it makes the trip go so fast," Guentzel said. "A couple games and you're already there."
Once they land in each destination, the team will take a bus from the airport to the hotel. After they arrive, the players grab their bags off the bus, file into the hotel and line up to get their room keys.
Once they get into their rooms, most of the guys will unpack their suits and dress shirts and hang them up but leave everything else in their bags. Though Hagelin admits that sometimes, he'll unpack just to make sure that he brought everything.
"I'm usually a guy that will forget like one pair of shoes on the road," he said. "I'll forget my phone once, my charger like five times per year."
There's a funny video of Crosby and Johnson from 2005, where the fellow top prospects were rooming together ahead of the NHL Draft and they were asked about the state of the room.
"I line up my shoes when we come in, try to get things organized," Crosby said. "He doesn't like that I lined up my shoes. He thinks it's on his side. So he decides to air out his equipment in the room, wet equipment that stinks. So I tell him no, you're not doing that. Our room's going to smell and I don't want my clothes to smell. He keeps doing it, so I have to take initiative and pack it myself.
"He doesn't like that idea. He starts messing around. He starts fighting me a little bit. Then he throws his gear bag in the closet with my suit that I have to wear to the draft. So I told him I basically might as well wear my half gear up when I get drafted because that's what I'm going to smell like."
Johnson's seen the video, and laughs when it's brought up. He claims that he's changed, and his room is much tidier now when he's on the road.
"I think that was me being a typical 17-year-old kid," Johnson joked. "I'm much more organized now. But I give all that credit to my wife. She's made me more organized."
No credit to Sid? "No," Johnson laughed. "That would be very unlike our relationship. I was organized about certain things but not about packing up my clothes. I had no style, stuff didn't match. I didn't care. I'm much better about it now."
It helps that the majority of players now get their own rooms on the road, something that was stipulated in the most recent Collective Bargaining Agreement. However, players on entry-level contracts still have to share rooms - with Casey DeSmith getting the exception whenever he is starting in goal.
That means Guentzel, despite being Crosby's linemate and a Stanley Cup champion, still has a roommate on the road. On the first road trip of the year to Montreal, Guentzel was paired with Juuso Riikola.
"I don't mind," Guentzel said. "I like it. It's nice to have someone to talk to, at least. I like being around people."
Despite what Guentzel's father Mike said when we visited Minnesota this summer - saying his son constantly leaves five of his six dresser drawers open - Jake claims he's not that messy.
"He was joking," Guentzel said. "I'm clean."
Once guys get into their rooms, some of them like to FaceTime or lie down and nap. Others like to walk around and explore. Cullen is part of the latter group.
"I don't want to just go in the room and just lay on the bed, so I try to get out and find a juice bar, get a juice or a smoothie or something," he said. "Haggy, usually he'll come with. There's a bunch of guys that'll hop in with me. I can give you a juice bar in just about every city. That's my favorite thing. I'll find a good juice bar and then if there's nothing like that I'll find an off-the radar coffee shop. Something just different."
A lot of the guys said they're glad Cullen is back because he's the go-to when it comes to juice bars and coffee shops, while Dumoulin is the expert on restaurants. Food is something Dumoulin has been passionate about for as long as he can remember, and he loves the challenge of locating new places to eat on the road.
"It's something I really enjoy," he said. "I hate when it's a bad meal and I waste my time on it, so I try to find a good meal."
The defenseman does his due diligence when it comes to research. He'll talk to guys that have lived in a city - for example, he'll get input from Kessel and Sheahan in Toronto - and he has two books he likes to reference. But Dumoulin will also go online, and while there's not necessarily one particular website he visits, he keeps an eye out for trends.
"If it pops up on Eater, if it pops up on Yelp, if it pops up on OpenTable, if you're seeing the same restaurant over and over again you know it's probably pretty good," he said. "Whether it be a chef, a restaurant or a good wine list, pretty much you can pinpoint at least one in these major cities that's worth going to, and especially one that you can get into."
When it comes to reservations, Dumoulin will make them in advance when they're traveling to a big city and plans to do so for Toronto and Vancouver. He's excited about what the restaurant scene will be like in Banff, somewhere he's never been before.
Dinners are something every guy looks forward to on the road, as that's when the best team bonding is done. They have a team dinner scheduled for Friday and then will be on their own for the rest of the trip, where the guys usually break up into smaller groups.
"We'll get a group text going with the guys that want to come," said Dumoulin, who was joined by Schultz, Guentzel, Maatta and Chad Ruhwedel for dinner in Montreal. "Some guys will be like nah, I'm going to stay in tonight. With numbers it's tough. That's why for the last couple years it was always me, 'Shears,' Scott Wilson and 'Schultzy' so we could always just book four. Four is a solid number, usually restaurants have it. It's tough to book in advance because you don't know if guys are in or guys are out."
"I think that's the most fun, just sitting with the boys," said Hagelin, who typically dines with Kessel and Hornqvist. "When you're in Pittsburgh, especially when you have a wife and kid you don't go out for dinner much, especially not with the guys on the team. So that's the fun part of being on the road."
After dinner, which usually lasts pretty long, some of the players will come back and play video games before going to bed.
In addition to their Nintendo Switches, the guys will tote their gaming systems in portable cases to use at the hotel. Dumoulin got one for Christmas, and Schultz said the rest of the guys had to buy them once they saw his.
"There's a group of us that have these portable cases that have a screen built into them," Rust said. "All you have to do is plug it in and it's good to go."
"Some guys have Xbox, Dumo and I play Playstation, but you can still play each other," Schultz added. "Like if Rusty has an Xbox and I have a Playstation, we can still play together. It just happened where it's cross-platform, but I think you can only do it for a couple of games."
They'll either go to someone's room and play each other while they're all sitting around, or play from their respective rooms. Dumoulin said they plan on looping Schultz in while he recovers from his surgery back in Pittsburgh.
Playing video games at the hotel is not something they do on every road trip, just long ones like this one.
"If we're going into a city the night before a game I don't bother packing it," Sheahan said of his Xbox. "But if we're going for a little longer where you know you've got some downtime, you bring it."
Brassard will sometimes join in, but other times he opts to just relax.
"Honestly, I like the hotel life," Brassard said. "Go for dinner, come back early and just lay in bed and watch TV. I feel like it's really, really relaxing. And sometimes the hotels will have really nice spas so you can go in the saunas and stuff."
At the end of the day, this is a business trip and the guys have a lot of obligations. They're constantly going from the plane to the bus to the rink to the airport. And all of the travel can be a grind, especially if the team flies out right after a game and doesn't get into their next hotel until 2 or 3 a.m., sometimes even later. They'll do that in Edmonton and Calgary.
"It's tough when you get in late and you play the next day or whatever it may be," Murray said. "You definitely have to learn how to fall asleep pretty much anywhere. I'm pretty good now. Early on I had a hard time. But you learn how to fall asleep basically wherever you are, which is huge, honestly, for our lifestyle. We're always traveling and getting in really late some nights. That's a skill that I think comes in handy."
When it comes to attendance and punctuality, the group is pretty good. It's drilled into these guys from the start of their careers that they can't be late, so they never are. Some guys, like Letang, do push it - which sometimes causes Crosby to worry - but he always comes through.
"Tanger always cuts it close, but he's never late," Crosby said with a laugh. "It's pretty good. Some guys like to nap a little bit longer than others, so the big nappers, you're always trying to make sure they're there because you don't want them to sleep through anything."
"I'm always last minute," Letang admitted. "I'm either really early or really late, there's no in between."
Twelve days is a long time to be on the road, and for a lot of the guys, it's tough to be away from family. But at least they're with their other family.
"It's great," Crosby said. "Your team is basically extended family. You spend just as much time with these guys as you do your family, really. I think you get excited because there's the challenge that comes with playing on the road, and it's just your group, that kind of thing. And especially because it's been a long time. Five months for me since I've been on a road trip with the guys. So I think you get excited for that."