Hotel Announcements
Rosewood Little Dix Bay brings Grand Slam tennis to the BVIs with return of Little Dix Bay Cup
Grand Slam champion Madison Keys and Olympian Jenny Brady headline an intimate three-day tennis weekend, with former ATP star and ESPN broadcaster Christopher Eubanks as emcee.
VIRGIN GORDA, BRITISH VIRGIN ISLANDS | AUGUST 18, 2026 – Rosewood Little Dix Bay will bring world-class tennis to the shores of Virgin Gorda with the return of the Little Dix Bay Cup, an intimate three-day tennis weekend offering guests rare access to some of the sport’s biggest names. Taking place December 4–6, 2026, the second annual event will be headlined by Grand Slam champion Madison Keys, alongside tennis pro and Olympian Jenny Brady, with American tennis star and ESPN broadcaster Christopher Eubanks serving as emcee.
The Cup returns at a moment when sport is taking on an increasingly prominent role in luxury travel, as travelers look beyond coveted seats for more personal ways to experience the games they follow. At Rosewood Little Dix Bay, that access unfolds in an entirely different setting: guests will step onto the court alongside the professionals, share a table with them and spend the weekend immersed in tennis against the natural beauty and peaceful seclusion of Virgin Gorda.
Following the incredible response to our inaugural Little Dix Bay Cup, we are thrilled to welcome guests back for a second year alongside an extraordinary lineup of talent. What makes this weekend so special is its intimacy. Guests have the opportunity to experience the game alongside some of its most accomplished players, while discovering the natural beauty, warmth and relaxed spirit that have defined Little Dix Bay for more than six decades.
Katya Herting, Managing Director, Rosewood Little Dix Bay
The weekend begins with an intimate Welcome Dinner and Meet & Greet, where guests will join Keys, Brady and Eubanks for an evening of conversation off the court. Saturday brings the signature Player Pro-Am, inviting guests to step onto the court and compete alongside the pros, followed by the Little Dix Bay Cup Player Tournament, where Keys and Brady will face off against the backdrop of Virgin Gorda’s lush green hills and Caribbean Sea.
The Cup concludes Sunday with a community tennis experience through Rosewood Impacts, connecting participating players with local youth and aspiring athletes from across the British Virgin Islands. The initiative reflects Rosewood Little Dix Bay’s longstanding commitment to the Virgin Gorda community, building on the resort’s continued support of local youth, education and community programs to create meaningful opportunities for the next generation.
Between matches, the weekend returns to the unhurried rhythm that has long defined Little Dix Bay. Guests can swim the resort’s pristine half-mile crescent beach, discover Virgin Gorda’s secluded coves by sea, restore at the cliffside Sense, A Rosewood Spa, or linger over Caribbean-inspired meals shaped by the surrounding land and ocean. The result is a tennis weekend that feels inseparable from its setting—pairing the energy of world-class sport with the peace, seclusion and connection to nature for which Little Dix Bay has been known for more than six decades.
Racquet sports are a natural extension of the active lifestyle at Rosewood Little Dix Bay, with six tennis courts and dedicated pickleball courts woven throughout the resort’s lush tropical landscape. Year-round, guests can take to the courts through private instruction, clinics and match play, creating opportunities for everyone from first-time players to seasoned enthusiasts to play amid the natural beauty of Virgin Gorda.
To learn more or make a reservation, please visit Rosewood Little Dix Bay’s website.
About the players
Madison Keys
Madison Keys is an American professional tennis player from Rock Island, Illinois, and one of the most accomplished players of her generation. Since turning professional at just 14 years old, she has remained a consistent presence at the highest levels of the sport, building a career defined by longevity, resilience, and success across more than a decade on the WTA Tour.
In 2025, Madison captured her first Grand Slam singles title at the Australian Open, completing a career milestone and reaching a career-high world ranking of No. 5. Throughout her career, she has reached multiple Grand Slam semifinals, finished runner-up at the 2017 US Open, and established herself as one of the game’s most consistent competitors. Madison has won 11 WTA singles titles and has recorded victories over many of the sport’s top-ranked players. Off the court, Madison is also well known for her charitable work and launching her own charity, Kindness Wins in 2020 and is a co-host of The Players Box alongside Jenny Brady, Jessica Pegula, and Desirae Krawczyk, giving fans an entertaining and candid look inside life on tour.
Jenny Brady
Jenny Brady is an accomplished American tennis player known for her powerful game, competitive resilience, and success on the sport’s biggest stages. A former World No. 13, Brady broke through at the highest level with a standout run to the semifinals of the 2020 US Open before reaching her first Grand Slam final at the 2021 Australian Open. She is also a WTA singles champion, capturing her maiden title at the 2020 Lexington Open.
After an extended period away from competition due to injury, Brady’s return to professional tennis has showcased the determination and perseverance that have defined her career. Her journey started as a collegiate tennis at UCLA to becoming one of the top-ranked players in the world. Off the court, she is a co-host of The Players Box alongside Madison Keys, Jessica Pegula, and Desirae Krawczyk, giving fans an entertaining and candid look inside life on tour.
Christopher Eubanks
Christopher Eubanks is an Atlanta native, former professional tennis player, and now a respected tennis commentator and broadcaster. A standout at Georgia Tech, Eubanks was a two-time All-American and two-time ACC Player of the Year before turning professional in 2017.
Eubanks had a breakthrough 2023 season. He captured his first ATP 250 Tour title at the Mallorca Championships, reached the quarterfinals at Wimbledon including a memorable five-set victory over world No. 5 Stefanos Tsitsipas and climbed to a career-high No. 29 in the ATP rankings.
Following his retirement from professional tennis in November 2025, Eubanks has transitioned naturally into broadcasting. His experience as a player, combined with his engaging personality, intelligence, and ability to explain the game from a player’s perspective, has made him a compelling voice in tennis coverage. He has worked as an analyst for ESPN and TNT Sports, while also appearing as a commentator and host for Tennis Channel.
Eubanks brings a unique perspective to the broadcast booth: he has competed against many of the world’s best players and experienced firsthand the highs and challenges of professional tennis. His journey from an under-the-radar junior in Atlanta to Wimbledon quarterfinalist and now broadcaster is one of perseverance, personality, and a lifelong passion for the sport.
About Rosewood
Rosewood is an ever-evolving global collection of hotels, resorts, and residences, born through the discovery of remarkable places. With 42 one-of-a-kind destinations, each property celebrates the culture and community that shapes it, upholding the ideal of hospitality as mutually revitalizing. Every detail is intricately woven to tell the story of the place, offering unexpected moments of discovery and connection. Rosewood Residences extends this spirit, inspiring a life where belonging and curiosity enrich every day.
For more information, please visit rosewoodhotelgroup.com
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About Rosewood Little Dix Bay
Rosewood Little Dix Bay is a secluded Caribbean retreat in complete harmony with nature. Hiding quietly among lush green mountains and pristine blue waters on Virgin Gorda, British Virgin Islands, a stay here invites the utmost peace and privacy. Imagined by renowned design studio Meyer Davis, the escape has 85 beach-facing rooms, suites, houses and villas that blend sleek modernism with simple organic materials. Whether indulging at the four dining destinations or taking a private picnic on white sands, nature is both a muse and source of seasonal cuisine. Think fresh wahoo, mahi and tuna brought by boat, paired with ocean-aged wine. From African ancestral healing traditions at Sense, A Rosewood Spa to educational swims with sea turtles to tennis matches with panoramic views, every experience fosters reconnection with the self and the natural world.
Discover more: rosewoodhotels.com/little-dix-bay-virgin-gorda
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