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 here.
