Shining a spotlight on celebrities and athletes who love to travel.
In the latest journey through The Overhead Compartment, we tag along with Sloane Stephens, who somehow manages to juggle pressure, travel, and island vibes like they are all part of her warm-up routine.
Sloane Stephens is embracing this phase of her career with a grounded confidence, shaped by her belief that pressure is a privilege and by the quiet routines that keep her steady — from journaling in the mornings to surrounding herself with people who bring her back to earth. Her 2017 comeback still reminds her to stay present and enjoy every “bonus round,” a mindset she carries with her to Virgin Gorda, a place she says instantly feels like where she’s meant to be.
That’s why she’s especially excited for the upcoming Little Dix Bay Cup, a world-class tennis weekend at Rosewood Little Dix Bay that blends elite competition with the softer, slower island pace she loves. The Overhead Compartment was excited to step out with Stephens and discover the perfect setting for her to connect with fans, share her passion for the sport, and celebrate the community that keeps her grounded on and off the court.
The Overhead Compartment with Sloane Stephens starts now….
OC: You’ve competed on the sport’s biggest stages. How has your approach to pressure and expectation evolved over the years?
SS: Honestly, I’ve learned to make peace with pressure. It used to feel heavy, like something I had to conquer. Now I see it as part of the job and a privilege. Pressure means people believe in you, and you believe in yourself. I just try to enjoy the ride a little more these days.
OC: Tennis demands so much mental strength. What practices or routines help you stay grounded through the highs and lows?
SS: Quiet mornings. A little journaling. A lot of deep breaths. And my people, I’m big on surrounding myself with folks who bring me back down to earth. If I can walk my dog, eat something good, and call my mom, I’m good.
OC: When you look back over your career, what moments stand out as turning points?
SS: Coming back from injury in 2017 changed everything for me. When you sit out for almost a year, you appreciate the sport differently. Every match felt like a bonus round. It reminded me that I truly love competing, even the messy parts.
OC: Your 2017 US Open win was iconic. What lessons from that still guide you today?
SS: Don’t overthink. Don’t get ahead of yourself. Trust your game and stay present. That whole run taught me that you don’t have to feel perfect to play great, sometimes belief is the magic ingredient.
OC: What’s one thing about your training that might surprise people?
SS: I take recovery VERY seriously. Like, Olympic-level commitment to stretching, massaging, icing, all of it. And I’m a big notes girl: I track everything. I’m basically a scientist with my body at this point.
OC: What advice do you give younger players?
SS: Play YOUR path, not someone else’s timeline. Protect your peace, ask questions, and remember that nobody figures this out alone. And have fun. It’s supposed to be fun!
OC: You’ve traveled everywhere. What makes Virgin Gorda and Rosewood Little Dix Bay special?
SS: It’s simply vibes. The views are insane, the water is unreal, and everything moves at a slower, softer pace. The minute I arrive, I take a deep breath like, “Yep… this is where I’m meant to be.” Community is connection. It’s the people who support you, push you, laugh with you, and show up when life gets chaotic. On tour, it’s the team and friends who keep me sane. Off court, it’s the kids and families we serve through my foundation. Community is everything.
OC: When you’re officially on island time, what’s your perfect day in paradise?
SS: Wake up slow. Big breakfast. Beach walk. Maybe some snorkeling because why not? Then a nap, a serious nap and a sunset dinner with something delicious and local. Perfect.
OC: First thing you do when you walk into a hotel room?
SS: Check the view. Always the view. Then I light a candle and move in like it’s my apartment.
OC: Complete the sentence: I never leave home without:
SS: My journal, my AirPods, and at least one Doc & Glo product. Usually the Deo, she goes everywhere with me.
Sloane Stephens, please use care upon departure as items may have shifted in The Overhead Compartment during our journey. Thanks for choosing us for your travel tips! Have a wonderful day!
