Each holiday season, as dusk settles over Biscayne Bay, a line of sailboats—glowing with twinkling lights and holiday spirit—pushes off from the dock at the Coconut Grove Sailing Club (CGSC). What unfolds is not just a parade, but a living tradition rooted in camaraderie, volunteerism, and the simple joy of being on the water together.

The CGSC Holiday Boat Parade officially began in 2009, as an idea sparked by Past Commodore Janice Pruett, who was serving as Cruising Chair at the time—back when the club had roughly 300 members.

“We were looking for ways to attract more people into the club, get more members involved, and introduce some fun community events,” Pruett recalled. “Yes, we wanted to attract new members—but we also wanted to open the doors of the club to non-members.”

That spirit of inclusion helped shape not only the Holiday Boat Parade, but a series of popular social events that followed, including Oktoberfest, a chili cook-off, the Haunted Mooring Field, and the Race Committee’s annual potluck party held each year on the first Tuesday of December.

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The First Parade: Small, Scrappy—and Unforgettable

The inaugural parade took place in December 2009, led by then-Commodore Dr. Nick Marten, on his own craft. He was followed in line by Janice, her husband and then-Vice Cruising Chair Alyn Pruett, and a small handful of other adventurous members.

That first year, fewer than six boats participated. “No one really knew the depth of the harbor or which route was best,” Pruett said with a laugh. “Only one boat ran aground that year—and that was Mooring Chair and Past Commodore Billy Beavers.”

Rules were few, but memorable. One was non-negotiable: the parade would go on rain or shine. Another quickly became legendary—if you didn’t have a boat, you had to bring a dish for the potluck party that followed. That rule practically guaranteed you’d be invited aboard one of the parade boats—especially if you showed up dressed in festive holiday attire.

A Parade That Grew—But Never Lost Its Soul

The Holiday Boat Parade has been held every year since its launch, with the exception of the pandemic years. Over time, participation grew, though the event has remained intentionally low-key and lightly publicized.

“It’s really about the people on the boats,” Pruett said. “It’s about enjoying a fun, relaxed time together out on the water—singing carols, laughing, and celebrating the season.”

Club tradition encourages captains to light up their boats using as many onboard lights as possible. And every year, Pruett arrives prepared—donning festive apparel while carrying spare holiday outfits to loan to fellow participants and extra lights for those who want to add a little more flair.

This year’s parade, held on December 14, 2025, featured more than 13 boats and was coordinated by current Cruising Chair Tom Cobin, with Commodore Priska Urban leading the procession.

How the Parade Works

The parade traditionally “steps off” at dusk on the third Sunday in December and wraps up following the onshore party by around 8 p.m. The route depends heavily on weather conditions.

If conditions are poor, the potluck celebration moves undercover at the club. When weather permits, captains gather their festive crews, ensure everyone is wearing a personal flotation device (PFD), and follow the Commodore off the dock.

From there, the illuminated fleet heads down the main channel, turns to parade past Dinner Key Marina piers 7 through 1, and circles the basin near Miami City Hall, Regatta Grove, Monty’s, and Coral Reef Yacht Club. In favorable conditions, the route may be extended through Brennan’s Channel and through the city’s live-aboard mooring field.

On shore, dozens of members, friends, and community residents gather on the club’s second-floor balcony and along the grounds to watch the glowing procession push off and later return.

More Than a Parade

The Holiday Boat Parade has become a meaningful part of a larger seasonal rhythm at CGSC. The Race Committee’s potluck party earlier in December—followed by youth sailors returning to the water for Orange Bowl Regatta training just days after Christmas—keeps the club buzzing throughout the holidays. Members then ring in the New Year together on December 31 with a more formal, dress-up celebration, enjoying fireworks launched just across Dinner Key at Regatta Grove.

Ultimately, the parade reflects Coconut Grove’s identity as one of Miami’s oldest waterfront neighborhoods and underscores CGSC’s enduring role as a steward of Biscayne Bay.

What began as a modest idea to bring people together has grown into a cherished tradition—one that lights up the Bay, honors maritime heritage, and reminds the community that sometimes, the best celebrations are the ones created simply for the joy of sharing the water.

“We wanted something fun, welcoming, and genuine,” Pruett added. “And that’s exactly what it’s become.”

With Art Basel having wrapped, The Grove Academy proved that local commitment to the arts doesn’t end when the galleries pack up. The school’s second annual student art showcase and auction brought families, community partners, and art enthusiasts together for an evening where the youngest voices in Coconut Grove’s creative community got their moment in the spotlight, and the bidding paddles were out in full swing.

The event took over the school’s newly expanded third floor, where student artwork lined the space on easels and display tables. The venue itself features permanent installations by local artist Rosie Ruiz Del Porto and her late father, Cuban figurative abstract artist Francisco Ruiz Del Porto, creating an inspiring backdrop where established and emerging artists shared the same walls.

Young artists across all grade levels selected their best work from the fall semester for display, presenting a varied collection that reflected the kids’ creative exploration throughout the school year thus far.

Going Once, Going Twice…

In a twist that brought real-world experience into the classroom, the school’s Student President and Student Government Association (SGA) officer took on auctioneer duties for both the live and silent bidding portions of the evening. The young leaders called out enthusiastic bids with the confidence of seasoned professionals.

“Everything we do ties back to real-world experience,” explained Betty Riera, founder of The Grove Academy. “Having our students serve as auctioneers gives them a valuable new experience and builds confidence in public speaking and leadership.”

When the Bidding Gets Competitive

Two students earned special recognition at the event. Seventh-grader Nathalie Avila and sixth-grader Skye Costa both showcased work that had recently earned them local honors from the Key Biscayne Lions Club, allowing them each to display two pieces.

Nathalie’s work was so well-received by the audience, it sparked an intense bidding. Two families went head-to-head for her piece, with the winning bid reaching $500, a big achievement for any artist.

But here’s where the story gets better: the winning family returned to the school the following day to give the artwork back to Nathalie, accompanied by an inspiring message encouraging her to never give up on her artistic dreams.

“You could see the excitement on the students’ faces when their pieces sold,” Riera noted. “For Nathalie especially, having that piece come back to her with such an encouraging message was truly special.”

Learning from the Pros

The Grove Academy has forged collaborative partnerships with Miami’s creative community including Abrakadooble Miami for art instruction, while students also trained under the direct mentorship of Rosie Ruiz Del Porto, whose minimalist and abstract approach has resonated strongly with students.

“Our students are very inspired by Rosie’s work,” Riera said. “Having them create under the guidance of a working local artist gives them insight into the professional art world and connects them to Miami’s vibrant creative community.”

That community connection extends throughout The Grove Academy’s curriculum, from cooking to music, movement to urban architectural design. Because why should creativity be confined to the classroom?

Beyond Pretty Pictures

The auction serves as one of the school’s primary annual fundraisers, channeling proceeds directly into enrichment programs. Entry remained accessible at $25 per person, with fundraising concentrated on the bidding for student artwork. Attendees also contributed direct donations.

“We’re trying to offer so many different entry points for students to discover their passions,” Riera explained. “The goal is to spark something in every child, and the support we receive from contributors goes a long way.”

A Tradition in the Making

As the event just finished its second year, it’s establishing itself as an annual celebration that connects young learners to Miami’s broader cultural landscape. The strategic timing alongside Art Basel sends a clear message to students: you’re participating in the same creative conversation happening throughout the city.

Drawing community partners, families, and local artists together, the evening reflected the collaborative spirit that defines both The Grove Academy and Coconut Grove itself. As the school continues to grow, the annual art showcase is shaping up to become a signature event, proof that some of Miami’s most exciting artistic voices are just getting started.

About The Grove Academy

The Grove Academy is an independent, community-driven school located in the heart of Coconut Grove. Through a personalized approach to learning, innovative curriculum, and strong community partnerships, the school fosters creativity, curiosity, and confidence in students from elementary through high school.

The Grove Academy is located at 3121 Commodore Plaza, Suite 200, Coconut Grove, FL 33133. For information contact The Grove Academy via email, call 305-796-5711, or visit The Grove Academy online.