Round Hill's ocean-view courts are set to host a tennis gathering that blends serious competition with Caribbean hospitality, unfolding across three nights and four days of masterclasses, exhibitions and open tournament play. The event draws together recreational players and former touring professionals on the same courts, a format that has quietly become one of the more distinctive stops on the resort tennis calendar.
This year's lineup features three names well known to followers of the men's and women's tours. Nicolás Almagro, a former World No. 9 and 13-time ATP Tour singles champion, built his reputation on clay with a one-handed backhand that troubled some of the best players of his generation; he was also part of Spain's Davis Cup-winning squad in 2008. Guillermo Cañas, a former World No. 8 and seven-time ATP Tour titlist who reached the French Open quarterfinals three times and won the 2002 Canada Masters, now runs his own academy in Miami and brings a coach's eye to the clinics. Joining them is Anett Kontaveit, who reached as high as World No. 2 and gives the weekend a strong women's tennis presence. Guests following the event online or planning travel around it can find further details through playinex, which has tracked similar tennis-and-lifestyle crossovers in the region. playinex
A Format Built for Access, Not Just Spectacle
What separates this weekend from a standard exhibition is its structure. Mornings are built around masterclass clinics with the featured professionals, followed by exhibition matches that let guests watch the pros compete at pace, and a pro-am tournament that puts amateur players directly into competitive doubles alongside them. It is a format designed to be participatory rather than purely spectator-driven, and that intent shapes the pricing as well. Full Event Registration, at $995 plus taxes per guest, covers every Cup event, tournament play, evening receptions and the Pro-Am. A separate Masterclass Pass, priced at $250 plus taxes per session, grants entry to one Morning Masterclass Clinic with a featured pro but does not carry Pro-Am eligibility, a distinction worth noting for guests deciding how deep they want their involvement to go.
Deliberately Small, Deliberately Personal
Organizers have kept spots limited by design, a decision that keeps instruction personal and ensures meaningful court time with each pro rather than a crowded rotation. It is a trade-off between scale and quality, and one that past editions suggest has paid off in guest experience if not in raw attendance numbers.
A Track Record With Grand Slam Names
This is not Round Hill's first run at elite tennis programming. Previous editions have brought in former World No. 5 Kevin Anderson, a two-time Grand Slam finalist at the US Open and Wimbledon; 2019 US Open champion Bianca Andrescu; former World No. 1 doubles player Marcelo Arévalo; and former World No. 5 Tommy Robredo. That roster places this year's edition within an established pattern rather than a one-off novelty, reinforcing the resort's position as a recurring stop for touring-level talent in an off-circuit setting.
The closing evening is pitched as the weekend's centerpiece, pairing competitive tennis with the kind of island hospitality Round Hill is known for. Guests interested in reserving a place are directed to contact the resort's concierge team at [email protected] with preferred dates and player numbers, as capacity constraints mean early inquiries are likely to matter.
