Join us for the Rosewood Little Dix Bay Cup, where you'll have the rare opportunity to connect with tennis legends. Set against the stunning backdrop of our resort’s courts, this exclusive tournament, taking place December 4-6, 2026, promises an unforgettable blend of world-class competition and luxury hospitality.

The weekend begins with an intimate Welcome Dinner and Meet & Greet, where guests will join Keys, Brady and Chris 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.