Ask anyone what Grey Oaks is built on and the answer arrives fast: three championship courses, 54 holes, a Pine Course that architect Andrew Green rebuilt hole by hole in 2023. That's the version of the club that shows up on plaques and in golf magazine rankings. It's also not where the club's energy is actually pointed this season.
The clearer signal sits on a set of courts most members walk past on their way to the first tee. Grey Oaks brought back its Pickleball Open this year for a second edition, and the way the club built that event says more about where its programming is headed than another year of course maintenance ever could.
A Title Sponsor, Not Just a Bracket
The Grey Oaks Pickleball Open isn't a members-only round robin squeezed between tee times. It's a branded tournament with an outside title sponsor, Aviance Capital Partners, and a fee structure that mirrors a competitive circuit stop rather than a club mixer: $75 per player plus $20 per division, with a player entering both the women's and mixed divisions paying $115 total. Matches run as round robins to 15, win by one, with the top four teams in each bracket advancing to gold and bronze matches played win by two.
That level of structure matters because of what happened the first time around. The inaugural event drew 125 registered players over its run in May 2025, a real number for a private club tournament that had never existed before. A second edition, with a returning sponsor and an established format, means the club is treating this as a fixture, not an experiment.
Compare that to golf. Grey Oaks has never staged a similarly branded, sponsor-backed open for members on any of its three courses. The Pine, Palm, and Estuary courses get renovations, ranking mentions, and quiet appreciation from the membership that already plays them. Pickleball got a name, a sponsor, and a bracket.
Every Club Has Courts. Few Have Staged an Open
Naples has earned its reputation as one of the country's most active pickleball markets, with well over a hundred dedicated courts spread across public parks and private clubs. Grey Oaks sits in a list of Naples country clubs that offer the sport, alongside Mediterra, Quail West, Fiddler's Creek, Lely Resort, Tiburón, and the Vineyards. Court access on its own isn't the differentiator. What separates a genuine program from a checked amenity box is whether a club turns access into an event people travel for.
That's the distinction worth sitting with. A club can install eight courts and call it done. Building a title-sponsored open with a scoring format, a bracket structure, and a returning field of competitors requires staff, planning, and a decision that the sport is worth promoting beyond the resident base. Grey Oaks made that decision twice now.
The Person Running the Program Just Became the State's Top Official
The clearest evidence that Grey Oaks is investing in racquets as a growth category rather than a maintenance line item sits in a personnel note that's easy to miss. Mike Curran, the club's Director of Racquets, served as USPTA Florida President for the 2024-2025 term. That's not an honorary title handed out for showing up. It meant the person who built Grey Oaks' daily programming, lesson structure, and league play was also the individual Florida's tennis teaching professionals chose to represent them statewide.
For members, that history still shapes the courts today: the instruction and organized play at Grey Oaks carries the judgment of someone whose standing in the sport reached well outside the gates. The club's golf side has its own strong bench, including Director of Golf Instruction Bob Usher, PGA. But it's the racquets program that put a Grey Oaks staff member in a statewide leadership seat.
Ten Courts, One Umbrella, Two Sports Sharing the Spotlight
None of this displaces tennis, which has been part of Grey Oaks since the club opened in 1993. The current program runs on ten Har-Tru courts, supporting everything from casual matches to club championship play. What's changed is that tennis no longer stands alone as the racquets identity. Pickleball now sits under the same programming umbrella, with its own tournament, its own sponsor, and its own growing field of competitors, while tennis continues to run its established leagues and clinics alongside it.
That's a meaningfully different picture from a club simply adding pickleball lines to existing tennis courts and calling it an upgrade. Grey Oaks built two active racquet sports, each with its own event calendar, under one director who now has statewide credibility behind his name.
What Happens After the Match
The other half of this season's story plays out at the table. Grey Oaks runs its wine and dining program under sommelier Victor Valdivia, a member of the Court of Master Sommeliers and the Chaîne des Rôtisseurs, who has built a cellar of more than 600 selections along with a rotating list of 25 wines available by the glass. Valdivia's approach to the job, as he described it in a Gulfshore Life profile of his work at the club, comes down to reading the moment rather than pushing a bottle.
"Anyone can sell wine, but a sommelier is creating a dining experience."
That experience runs alongside a kitchen led by Executive Chef Derin Moore, an ACF Certified Master Chef whose mentoring work was recently featured as a cover story in Golf Kitchen magazine. The kitchen sources from local purveyors and artisans, pulling in ingredients that range from Florida watermelon to wild gulf grouper depending on the season, which means the menu shifts with what's actually available in Southwest Florida rather than running a fixed rotation year round.
Put the two pieces together and the pattern becomes obvious. A member plays a pickleball match in the morning, catches a tennis clinic in the afternoon, and closes the day with a chef-driven dinner and a wine pairing chosen by a Master Sommelier level professional. That full loop, sport to table, is what the club's programming has been quietly built around this season.
A Season Written on the Courts, Not Just the Greens
None of this makes the golf side irrelevant. The Pine Course renovation still stands as one of the more significant course investments in Naples private club history, and the club's three-course, 54-hole footprint remains a real draw for members who came to Grey Oaks for the golf first. But golf's story this year is stability. Racquets and dining are where the club is actively building something new, event by event and hire by hire.
For anyone living inside the gates, that distinction changes where the calendar actually points this fall and winter. The tournament dates, the clinic schedule, and the dinner reservations built around match nights are where Grey Oaks is putting its effort right now. The golf courses will still be there in perfect condition. The energy has moved next door.
If you're weighing what a season at a club like Grey Oaks actually looks like day to day, or you're comparing it against other Naples country club communities before making a move of your own, Chiodo Group can walk you through what membership, lifestyle, and property options look like across Collier County's private clubs. Reach out for a conversation grounded in what these communities are actually doing this year, not just what their brochures say.
