It seems a fitting first step for Gaston, who knows the time is right for welcoming retirement. He felt forced onto that island more than a decade ago, but things are different now. Gaston is stepping aside as manager of the Blue Jays, and he is doing so on his terms.
That includes, before anything else, a week spent surrounded by palm trees, sunshine and, most importantly, some close friends.
"We've been planning it for a while," said Blue Jays bench coach Nick Leyva, who paused before offering a smirk. "He finally came through with his word."
Leyva paused and quickly took a grateful tone.
"He's such a generous man," Leyva said.
All Gaston has brought to Toronto are a pair of World Series championships and more than 900 victories over two stints as the manager of the ballclub. His reputation has been built around those two titles in 1992-93, but his contributions to the Blue Jays' organization extend beyond those glory years.
His name has become synonymous with Blue Jays baseball, and he has made a home in Toronto for years, often referring to Canada as his second home. Gaston has worked as a coach or manager with the team for parts of 21 seasons, but simply serving as a teacher is something that has brought him much pride.
"The one thing I'll miss in this game is teaching," said the 66-year-old Gaston. "I still like to teach. I like to see guys be successful with what we're trying to teach them."
Gaston made it known before this season that it would be his last as manager of the Blue Jays, choosing to move into an advisory role with the club next year. Under those circumstances, Gaston viewed his role this year primarily as a teacher, helping usher Toronto into a new era in the franchise's history.
Ever the perfectionist, Gaston will not leave the manager's chair entirely satisfied.
"There's still a lot of work to do, but I think we've done OK," Gaston said. "It could be better. But sometimes people have to be receptive to what you're saying, or they have to believe in it. Sometimes it takes more than six months to do that."
That mindset fits Gaston's character.
"He's a winner," Leyva said. "That's one of the biggest things that I've learned from him. He expects to win every single game. No matter who you're playing, no matter who's pitching, he comes to the ballpark with one thing in mind, and that's just to go out and win that ballgame, however he can."
After Gaston took the helm in June 2008, following an 11-year absence from managing, the Blue Jays responded by going 51-37. A year ago, Toronto bolted to a 27-14 record out of the gates, serving as an early-season surprise before fading down the stretch. With 13 games remaining this year, the Jays have already matched the 75 wins they put up in 2009.
"There was an excitement that year," said Blue Jays general manager Alex Anthopoulos, referring to 2008. "There was an excitement at the beginning of last year. From my standpoint, that's probably the most excited and rejuvenated I've seen the fan base, and I think that all tied into Cito's return to the club."
That excitement has continued to increase as fans have watched Anthopoulos put his mark on the organization, trying to reach the heights the club experienced in the early '90s. That makes Anthopoulos' next move -- finding a successor for Gaston -- an intriguing one for Toronto's faithful.
Anthopoulos is already knee-deep in the hunt for a new manager, but he said the process could easily last into November. As for what he is looking for in a new skipper, Anthopolous was not prepared to comment, though finding someone with some level of Major League experience -- as a player, coach or manager -- appears important.
"I don't have a criteria," Anthopoulos said. "There are certain traits I think anybody would agree that everyone looks for in a successful manager. But I'm really not tied down to any style, whether it's a first-time manager or an experienced guy, or it's age or background, I'm really not limiting myself at all. I'm being incredibly open-minded."
That said, replacing an organization icon such as Gaston is no easy task.
"[Gaston's] brought a lot of stability," Anthopoulos said. "There's no question he symbolizes and really personifies the best years that this organization has ever had, but also what the organization wants to represent from an on-field standpoint -- winning championships."
Gaston is softspoken by nature and quick to joke around or weave a tale of his experiences in baseball. At the same time, he is a fierce competitor and operates with the stubbornness and bravado characteristic of his generation. That has led to clashes with others at times, but Gaston is loyal to his friends and family, caring about his players and unwavering in his beliefs.
"Cito has such a great way about him," Anthopoulos said. "We say it all the time: If you can't play for Cito, you can't play for anybody. He's such a good person, a good human being. He always puts family first. But, at the same time, he can be intense."
Leyva smiles at that contrast.
"He has his own way of doing it," Leyva said. "I said to him one day, 'Man, I can't hear you half the time you're talking to me. He said, 'Yeah, you do.' He talks soft, but it makes you listen and makes you pay attention."
Leyva has served on Gaston's current coaching staff since they rejoined the Blue Jays midway through the 2008 season, and he also coached under the manager from 1993-97. Being a part of both eras gives Leyva a unique perspective on Gaston's legacy and accomplishments.
During the World Series years, it was easier to pile up wins, given that Toronto boasted baseball's biggest payroll, along with an All-Star cast of players. Over the past two-and-a-half seasons, Toronto's roster has seen drastic changes, and the club began featuring a youthful pitching staff as it has prepared for the future.
Still, Gaston found ways to post more wins than expected.
"We had some really good teams back then," Leyva said. "When you have the talent that we had, I think his job then was to just make sure that you put them in the right place at the right time. Since we've been back, I actually think he's done ... not a better job, but he's had to manage a little bit more.
"He's had different personnel, he's had different matchups and I think he's had to really look at it. He's had to mix and match, and I think he's done a pretty good job."
Gaston is also willing to give his players a chance to succeed.
One example can be found in Jose Bautista, who was labeled as a utility man when he joined the Jays in August of 2008. He struggled throughout much of the past two years, but Gaston held out faith that Bautista would break through with more playing time. This season, Bautista has blossomed into one of baseball's biggest stories with 49 home runs.
"If he sees talent in you and he believes in you," Bautista said recently, "he's going to try to let you play at some point. He must have seen something in me. I do really appreciate the opportunities he's given me and the confidence that he's given me as well."
"He doesn't say much to us as pitchers," Blue Jays left-hander Ricky Romero said. "But when he does, you listen. He's kept us in check [and] relaxed, and he's just let us go out there and play. To play for a guy who won back-to-back World Series is pretty cool.
"He obviously knows what it takes to win. We just couldn't get it done in the years that he was here. It's been a fun experience having him here."
Gaston, dismissed in 1997 to conclude his first stint as Toronto's manager, was not able to bring any more banners to Rogers Centre in his second tour with the ballclub. He does feel, however, that the Blue Jays are heading in the right direction, as he heads into retirement.
"It's in good shape," Gaston said of the ballclub. "It's just making sure it stays that way and goes forward. We're in a good spot right now."
Gaston will be in a good spot in a few weeks, feet up, drink in hand and the Pacific Ocean in his sights.
Gaston plans on taking Leyva and Gene Tenace, another of his former coaches, on the one-week vacation to Hawaii. After that, Gaston has a check list of other trips he would like to complete with his wife, Lynda, before it is all said and done.
A tour of Europe. A visit to Australia and New Zealand. And a stop in South Africa.
"Then," Gaston said, "I think I'd be done."