"Spend all our time together all year then go to the same place": Maldives becomes holiday destination of choice as Pegula, Brady, Keys, Krawczyk debate why

Thursday, 27 November 2025 at 09:11

Jessica Pegula on court at the WTA Finals.

In a lively episode of The Players Box podcast, Madison Keys, Jessica Pegula, Jennifer Brady, and Desirae Krawczyk gave fans a candid look into the lives of professional tennis players off the court. From dream vacations to personal milestones and reflections on their peers’ retirements, the conversation revealed the personalities behind the rankings.

The Maldives: Tennis’ most popular vacation

The discussion opened with the perennial topic of the Maldives, a destination seemingly loved by every European tennis player.

“We’ve never been to the Maldives,” Keys admitted. “It seems like every other tennis player vacations there. We spend all our time together all year, and then all of us go to the same place and hang out. I don’t know if there are multiple resorts, but it’s quite literally everyone.”

The players began listing the stars who made the trip: Mertens, Sabalenka, Potapova, Ostapenko, Bencic, Vekic.“Every year, everyone goes except for us,” Keys said.

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They speculated whether players are drawn there for the scenery, winter escapes, or maybe special perks. “I’m sure they get some sort of perk, maybe a discounted rate or a couple of rooms for free,” Krawczyk added.

Brady and Pegula chimed in with observations about the logistics. “It’s such a trek. Two days to get there!” said Brady. Krawczyk noted that even some Americans, like Taylor Fritz, occasionally make the journey.

The four joked about a future visit: “Maybe we all four can go,” Keys said. “Players Box podcast goes to the Maldives! We can have so many guests.”

Desirae Krawczyk’s Egg-Freezing Journey

The conversation became more personal as Pegula asked Krawczyk about her recent egg-freezing procedure.

“I’m done with my shots, and I’m really happy I did it,” Krawczyk shared. “I didn’t have a specific number of eggs I wanted—just hoping for as many as possible, and it worked out. The procedure was quick, under twilight anesthesia, and I was out an hour later.”

Krawczyk detailed the injections, which required careful timing, even while attending a bachelorette party. “Jenny was helping me stay focused, making sure I didn’t get distracted. After a few days, I felt better than I expected. No regrets—it was worth it,” she said.

She also emphasized the importance of open discussion around egg freezing. “Talking about it helps other women feel more comfortable exploring their options. If you have the funds and it’s an insurance policy, why not?”

Christopher Eubanks in happier times at Wimbledon.

Christopher Eubanks saw his career end recently.

Reflections on retirement

The conversation turned to the recent retirements of Chris Eubanks and Lauren Davis. Keys reflected on their careers with admiration:

“Fans often equate success with winning Grand Slams, but you can have an incredible career without that. Chris and Lauren did everything they wanted and are moving on happily. That’s inspiring.”

Brady added, “It’s about having no regrets. As long as you can look back and say you did what you wanted, that’s a successful career.”

The players discussed the skewed perceptions of success in tennis, noting that the dominance of Novak Djokovic, Rafa Nadal, Roger Federer, and Serena Williams has raised expectations unrealistically. “Winning one Grand Slam is huge,” Keys said. “We shouldn’t discount everything else players achieve.”

They also discussed insights from other pros. “Andy Murray said he wished he enjoyed his career more instead of chasing goals,” Krawczyk said. “Chris and Lauren, they have no regrets—they did everything they wanted and then moved on.”

The players agreed that happiness and fulfillment in one’s career are ultimately more important than rankings or titles.

Ostapenko’s Instagram Marketplace

The conversation lightened with a shout-out to Jelena Ostapenko, who has created a private Instagram marketplace selling items from vacuum cleaners to clothes and perfumes.

“It’s private, she controls it, and kudos to her,” Pegula said. “Keep selling your stuff!”

Keys joked that maybe Ostapenko’s side hustle “paid for the Maldives vacation.” The group teased potential collaborations, even imagining Ostapenko selling their items for a commission. “I’d totally give it to her and get a kickback,” Krawczyk said.

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Samuel GillEditor-in-Chief

Samuel Gill is the Chief Content Officer (CCO) of TennisUpToDate.com, a role he has held since 2020. He is responsible for editorial governance across the platform, including setting content standards, overseeing accuracy and consistency, and guiding long-term editorial strategy. Since joining, he has contributed more than 10,000 articles and editorial pieces across the TennisUpToDate network, playing a central role in the daily operation and development of the site.

Based in Leicester, Samuel has a broad background in tennis media. In his current role, he works closely with editors and writers to ensure coverage meets clear journalistic standards, with particular attention to verification, consistency, and timely updates when new information becomes available.

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