Creative Tailgating at the Windsor Charity Polo Cup

In 1990, the classic film Pretty Woman mainstreamed Julia Roberts, flying escargot, and the cherished polo tradition of the “stomping of the divots.” Moviegoers were instantly smitten with the character of Vivian Ward, who stomped divots while wearing a chic hat with a brown-and-white polka-dotted dress. Suddenly, polo and its glamorous tailgating customs were the talk of the town.

This chatter finds a home again in 2026, as tailgaters for the biennial Windsor Charity Polo Cup plan their tents around this year’s theme of “Love Is All Around Us.” Inspired by Love Actually, another romantic comedy, this year’s theme honors the February 14 Polo Cup date as well as polo’s innate spectator involvement and engaging atmosphere.

Held every two years since 2012, the Polo Cup has raised funds for various local nonprofits. According to Windsor’s marketing director, Jane Smalley, the event was born from the desire to use polo to support the community. “Windsor was founded by equestrians who love to play polo in the winter,” she explains. “When our founders came across land that was abandoned after the citrus freeze, the first thing they built was the polo field. This Charity Polo Cup harkens back to the beginning; it is part of the heritage of Windsor.”

Multiple charities benefit each time; this year’s focus is on three Vero Beach organizations that support underprivileged children: Childcare Resources of Indian River, the Environmental Learning Center, and Crossover Mission. To ensure maximum fundraising potential, the Polo Cup team tapped into polo’s most honored tradition of tailgating to offer its spectators multiple ways to enjoy the event.

Tailgating at a polo match puts its spectators almost directly into the action. Most tailgaters sit within 3 feet of the playing field, which allows an almost visceral interaction with the players. Pounding hooves and the player’s frustrations and elations can all be felt from this short distance. While some may worry that the proximity can be a distraction, Max Secunda, Windsor’s director of equestrian operations and match director, assures, “If you have a young horse, he or she may be affected the first time or two, but they get used to it. Large crowds are an asset, because when the tailgaters are asked to stomp the divots, they can reestablish the field. The field may be destroyed, but the conditions can be totally renewed.”

This welcoming atmosphere that encourages spectators to literally become part of the game is indicative of the event itself. In the Polo Cup match, the teams of four consist of three professionals and one amateur, and all play gratis. Sometimes, the teams are not formed until the day before the event due to the players’ tournament schedule, but coed teams with players such as Nacho Figueras and Hope Arellano delight fans each time.

Spectators cheer on these teams in two different ways. One side of the field is dominated by an elegant tent serving a catered luncheon to approximately 650 sponsors and observers. The other side of the field offers the more relaxed tailgating option, which involves individualized tents, a competition, and prizes.

A family or group of friends that opts for one of the 85 tailgating spaces is allotted a 10-by-20 tent for six people; they decorate it to match the event’s theme, to whatever degree they choose. Some purchase two tents to join together and form a larger group. Food, drink, costumes, and decorations abound in great variety, and the energy is palpable, as tailgating participants know their tents will be judged for the competition.

Windsor member Stacey Lewis oversees the tailgating competition. “The tailgating started in the backs of people’s cars,” she explains, “but we wanted it to become as exciting as sitting under the glamorous tents on the side of the field.” This option allowed multiple generations of families to come together for an afternoon of fun.

Part of Lewis’ role is to reach out to each group to help bring their ideas to life and to ensure no two tents are exactly the same. While many will opt to bring this year’s “Love Is All Around Us” theme to life, others will take a more relaxed approach. For example, since this theme celebrates love on the big and small screen as well as romantic locations, Lewis says, “You don’t have to do the theme; you could just come nicely dressed and put an Eiffel tower on the table.”

Many tailgaters will embrace the theme wholeheartedly, however, such as Barb Kaytes and Sally Griffin, who won third place in the 2024 competition with their families.
While both families had always attended the Polo Cup luncheon and enjoyed the fine food and hospitality, they met some fellow members who introduced them to the tailgating tents during the stomping of the divots.

Griffin explains, “From the tent side, we would often run into friends who were from the tailgate side and were often invited over to their individual tents. This is where we first saw the level of enthusiasm expressed in both costume and creativity. On the tailgate side everyone was having a sort of themed block party. It was just so much fun!”

According to Griffin, Kaytes convinced the families, including the children and grandchildren, to try tailgating, and their first tent had a Greek forum theme. Griffin says, “Our tent featured Greek columns, frescoes, and a scenic background, along with Greek statues and traditional Greek food.” While their first foray involved embellishing the tent with a sea of foam-board cutouts, incorporating perfectly matched costumes, and serving complimentary food, Kaytes reflects, “It doesn’t have to be a ton of work. You just need to think about how to involve all the five senses. Have a strong, clean, distinctive theme.” She also encourages finger foods and portable drinks to encourage others to visit the tent.

For serious competitors, the event promises creative-minded, unbiased judges and elaborate prizes that are often donated for the cause. This year, the competition is judged by Xaque Gruber, an artist, writer, and filmmaker who teaches at the Vero Beach Museum of Art. Past prizes have been a fine arts package from the VBMA and a Hinckley boating tour. Smalley excitedly shares that this year, “one of our beneficiaries, the Environmental Learning Center, donated a private sunset cruise on their pontoon boat for up to 16 people. Windsor will be catering it. This will be given to the first-place tailgate.”

The idea of a beneficiary giving back to the event as a gesture of thanks is a full-circle moment the Windsor Charity Polo Cup celebrates. Organizers and sponsors know that as the popularity of this event grows, so does support for the charities. Everyone from the tailgaters to the players who donate their time knows that while this event brings festivity and fun, it also has the power to uplift those in need. There is no greater honor for supporters of a sport than to take part in the goodwill it promotes with community outreach.

Derek Gores

There is perhaps no better artistic match for the Windsor Charity Polo Cup than Derek Gores. While polo encourages interaction with its spectators, Gores believes people should interact with art. His gallery in Eau Gallie shares space with an indoor miniature golf course where each hole was created by a local artist. This conscious choice came from his realization that while people were happy to walk by and look at art, they really liked being entertained by it.

This understanding may come from Gores’ affinity for the collage medium. “Collages keep the creativity flowing, and the medium is so raw,” he says. Collages allow him to control an image but also let him take his viewers down new rabbit holes every time they look at a piece.

Commissioned to create a collage to be auctioned at this year’s Windsor Charity Polo Cup, he knew he wanted it to commemorate the event and the majestic animal at its core; but upon closer inspection, he wants viewers to see fragments of Windsor life and past polo events. He will create these layers with donated items from the event’s organizers, such as photos, programs, drink recipes, menus, and raffle tickets—all items that are used in the day-to-day life of the event but wouldn’t necessarily be considered “art.”

This is the same course of action he followed while creating his Kentucky Derby and Kentucky Oaks collages as the official artist of these events. After all, as he knows, “Old objects have energy and tell a story.”