He won't make the same mistake twice when he brings the Cup home again on July 15-16.
"I was pretty happy with what I did in those few days [in 2009], to be honest with you. I couldn't believe I squeezed that much in two days," Crosby said with a smile. "I didn't know there was enough time to get that much in. If anything, I went to bed pretty early the first night because I got the Cup early and had a really early morning, starting out the next day, and I told myself I'm not going to go to bed that early next time. I'm going to find a way to get through those two days with as little sleep as possible. I'm going to enjoy it.
"Going back to '09, we thought it was going to be an annual thing, so this time I appreciate it a little more and I'll make sure I spend every second I possibly can with it."
Bringing the Cup back here to celebrate with the community that helped mold him into a two-time Stanley Cup champion and Conn Smythe winner was a no-brainer.
"It just feels right," Crosby said.
He's spending the first part of his week running his second annual hockey camp. There are 160 kids from all around the world attending the camp, and Crosby's hands-on when it comes to all activities, both on and off the ice, Monday through Friday. It will conclude with a Stanley Cup parade.
"We've got a lot of things planned," Crosby said with a smile. "I don't know if I want to necessarily going into details, but we have a lot of things planned. The biggest thing is you want to enjoy it, it goes by quick. You try to get it to as many people as possible, let as many people enjoy it because, for me, that's one of the best parts just seeing the reaction on peoples' faces. A lot of times people who don't necessarily expect to see it and sometimes that's the best part of it. It'll be a busy schedule, but there's lots on it."
Crosby acknowledged the parade will be a bit shorter than it was in 2009, but other than that, he expects it to be similar.
"I'm hoping it's a great turnout," he said. "I know last time it was. I know people are excited from the people I've talked to, so it's pretty special to be bringing it all the way through here and down to the rink. It's really nice and I'm expecting it to be a lot of fun."
The parade kicks off at 10:30 a.m., but locals begin to camp out as early as 6 a.m. to get a glimpse of their hometown boy with the Stanley Cup.
The Penguins defeated the San Jose Sharks in six games to hoist hockey's sacred chalice on June 12. It was the second title for Crosby and his third trip (2008) to the finals.
"You appreciate it more," Crosby said. "Having gone seasons where you fall up short, and there are high expectations, this year is kind of different season, the way it went -- a story of two teams, really. Having gone through those things in the past, I probably appreciate it more."
Along with running his hockey camp, preparing for a two-day celebration, Crosby also said he started working out again in preparation for the 2016-17 season this week.
"It's a pretty short summer, and that's the challenge for going deep into the playoffs," Crosby said. "You've got to find a way to manage the work and rest at the same time. With the World Cup being right around the corner, it'll be a busy summer, but I feel like a big part of why I come home is you get that feel of being relaxed even though you're training and you're around friends and family, you get away from things a little bit, and that's definitely important."
As far as a return trip to the Stanley Cup finals in 2017, Crosby hopes that's the case, but he also understands how difficult it is to reach that point of the season, let alone win back-to-back championships. In fact, the Detroit Red Wings were the last team to accomplish the feat in 1996-97 and 1997-98.
"Yeah, I'd love to be back," he said. "It's not too easy. You don't see too many teams do it. We were able to [return in back-to-back seasons] in '08-09 and it's really a tough road, especially when you're talking about World Cup right around the corner and a lot of hockey to be played. It's going to be a challenge, but you do understand it's tough to get there and it's something you try to take in as much as you can when you win it."