Record fundraising marks Naples’ bustling gala season

When it comes to hoisting auction paddles to support local nonprofits, Naples gala patrons were on a record-setting roll during the 2024-25 season. And while it was far from alone, the Naples Winter Wine Festival led the charge. In 2025, the marquee event raised more than $34 million for the Naples Children Foundation, formerly the Naples Children and Education Foundation, benefiting nearly 50 area organizations.

For perspective, the Met Gala — the hyper-glam New York fundraiser that supports the Costume Institute at the Metropolitan Museum of Art each May, backed by global celebrities, fashion icons and former Vogue editor-in-chief Anna Wintour — raised $31 million in 2025.

Here in Naples, during what Gulfshore Business has dubbed “paddle season” — a season within a season, filled with galas galore — generosity flowed freely. 

Many nonprofits also set new records, with more than $47.5 million raised across 30 events, held between November 2024 and March 2025 (see pg. 60). While not exhaustive, this list focuses on galas featuring auctions or fund-a-need paddle raises, with a few exceptions. Together, they reflect a banner year for nonprofits supporting causes from the arts and education to health, social services, seniors and the environment.

A look at what makes Naples galas tick shows that local nonprofits have big-event fundraising down to both an art and a science. Yet with shifting economic and political currents, some are wondering whether paddle season will look different this year.

The magic behind the millions

What’s behind the money-raising magic that might make Wintour — still in charge of the Met Gala even after stepping down as chief editor of American Vogue — and her deputies wonder what’s going on down here in Naples?

How do local nonprofits bring their missions to life in ways that keep donors dressing up, showing up and putting up those paddles again and again?

Maria Jimenez-Lara, CEO of Naples Children Foundation, said Naples philanthropists support the organization through the Naples Winter Wine Festival, which marked its 25th anniversary in 2025, because they see the mission in action.

“I think they embrace our mission because they see the profound and lasting impact their support creates,” Jimenez-Lara says. “Many donors call Naples home, and they care deeply about children, regardless of circumstance, and understand the need for resources so kids can succeed.”

She adds that accountability is key: “They know that when they give through NCF, their contribution is thoughtfully tracked; it’s measured.”

The heart of the matter

For the American Heart Association, the focus in 2025 was education — teaching the community how to perform CPR and use an automated external defibrillator. Donors rallied.

“What we’re trying to do is build the chain of survival in Southwest Florida when it comes to cardiac arrest,” says Jessaca Rodriguez, the association’s Southwest Florida executive director. “Currently, nine out of 10 cardiac arrests occur outside a hospital. In 90% of those cases, the victim dies because CPR isn’t performed adequately or in time.”

The message hit home at the Heart Ball, where 550 guests heard the story of 7-year-old Oscar Stuebe of Palm Beach. After being struck in the chest by a baseball, his mother, Sarah, saved his life by calling 911 and performing CPR.

The Heart Ball raised a record $850,000. And when Oscar and his family took the stage, there was hardly a dry eye in the house.

A Starry Night for youth

At Youth Haven’s Starry Night Gala, which raised a record $2.5 million, more than 500 guests heard from an alumna of Rob’s Cottage, the organization’s homeless teen program.

The young woman, who turned 20 the night of the gala, shared how Youth Haven changed her path, helping her attend college and thrive.

“For our supporters, it’s a chance to see the difference they make,” says Youth Haven CEO Linda Goldfield.

She also invited all the Rob’s Cottage teens to attend. “It’s a 90% success [program], ensuring that homeless teens in this community don’t become homeless adults,” Goldfield says. “Hearing those stories firsthand makes a difference.”

Curtain call at Gulfshore Playhouse

In the arts arena, Gulfshore Playhouse dazzled 455 guests at its Once Upon a Dream Gala at The Ritz-Carlton Naples, Tiburón. The event celebrated the new $72 million Baker Theater and Education Center with show-stopping performances.

This gala brought laughter and applause rather than tears, showcasing the theater’s mission to create world-class productions and unique education opportunities in Naples.

“Our gala is like the ‘anti-gala’ — it’s 95% entertaining and 5% fundraising,” says Kristen Coury, founder, CEO and producing artistic director. “We don’t have a live auction or a silent auction. We entertain while making the case for why this organization matters.”

The 2025 event raised nearly $2.6 million. More importantly, Coury said, it was a celebration of completion. “We could finally say, ‘Hey, we did that all together, and thank you for your support.’”

Looking ahead

Will political and economic uncertainties — including a sustained drop in Canadian visitors during 2025 — affect giving in the 2025-26 season?

“There’s a lot happening economically, so I don’t have a real prediction in terms of how much we’re going to raise [at NWWF],” Jimenez-Lara says. “It’s the 26th year, and after anniversary years, there can be shifts. But we’re adjusting our strategy and staying ahead of any change.”

Still, she remains optimistic: “We’ll continue to see generosity. And if we need to, we’ll pivot and partner to ensure the needs are funded.”

Coury agrees. “When tariff plans rolled out [earlier in 2025], there was concern we were headed toward recession. But lately, the stock market seems to close at record highs every night.”

After two hurricanes and a pandemic in the past decade, Gulfshore Playhouse has learned to adapt. “If something serious comes along, we’ll pivot,” Coury says.

At Youth Haven, Goldfield remains confident in Naples’ philanthropic strength. “Ninety percent of our budget comes from community support,” she says. “We live in one of the most generous communities anywhere. If any place is insulated from uncertainty, I believe it’s ours — for the children we serve.” 

NCH puts paddles away

While traditional galas with lavish production values remain the norm for most area nonprofits, one of Naples’ leading organizations is stepping away from the paddle-raising model — at least for this season.

As Naples Comprehensive Health, the largest health care system in Collier County, prepares to celebrate its 70th anniversary in 2026, the organization is shaking things up with a series of intimate fundraising dinners spread throughout the season.

Mara Hammond, chief impact officer at NCH, said the system wants to “reimagine” its fundraising approach after hearing from gala attendees and longtime donors who were “open to an alternate method.”

“In prior years, we would have large-scale, 300-plus-person events,” Hammond says. “We’re moving away from that model to create a series of more intimate, higher-impact gatherings. These experiences are intended to bring the right people together at the right time and create space for deeper conversation and stronger connections — the kind that are hard to achieve in a big room with a lot of people in a short timeframe.”

Between five and seven dinners, each with 20 to 50 guests, began in November and will continue through March. Hosted by “change makers and influencers and friends of the organization,” the events are designed to connect existing donors while also introducing new supporters to NCH.

The series will culminate in a scaled-back NCH Ball in April — the 67th annual event. This, the organization said, makes it the longest-running annual event in Naples. The 2025 Ball drew 480 guests and raised $3.1 million.

This year’s Ball, Hammond said, will be “more about celebration and not a high fundraising target.”

In addition to marking the 70th anniversary, the event will highlight progress on two major projects launched under President and CEO Paul Hiltz: the R.M. Schulze Family Heart and Stroke Critical Care Center, and the Hospital for Special Surgery at NCH orthopedic surgical center.

“This year really is a turning point for NCH in so many ways, with the major investments that have been activated since Paul’s arrival (in 2019),” Hammond says. “We’re in the final stages of closing the funding gaps for those projects, and we’re about to launch the next phase. To achieve those priorities responsibly, we want to make sure we’re putting our dollars where they can make the most impact.”

Paddle Season Totals 2025 Events

ARTS

Artis—Naples

Friends of Artis—Naples Springtime Harmonies March 16

Guests: 275 | $1.8 million*

Gulfshore Playhouse

Once Upon a Dream Gala 

March 3

Guests: 455 | $2,581,100

Naples Art Institute

Scene to be Seen 

Feb. 8

Guests: 300 | $422,584

Opera Naples

An Evening in Paris Gala 

Dec. 5

Guests: 250 | $482,819

The Naples Players

Front & Center Gala 

Feb. 11

Guests: 220 | $2.5 million*

Total: $7,786,503

CHILDREN & EDUCATION 

SENIORS

SOCIAL SERVICES

Baker Senior Center 

of Naples

An Evening for Better Tomorrows 

Jan. 11

Guests: 250 | $1.1 million

Better Together

Night of a Million Dreams 

Feb. 18

Guests: 225 | $621,050*

Champions for Learning

Night for Champions 

Feb. 15

Guests: 340 | $1.1 million*

C’MON (Golisano Children’s Museum of Naples)

Night at the Museum: 

The Color Factory 

Feb. 8

Guests: 400 | $1.5 million

Community School 

of Naples

Flight of Fashion 

March 15

Guests: 450 | $1.16 million

Fostering Success

Candy Dreams Gala 

March 1

Guests: 300+ | $700,000*

Fun Time Early 

Childhood Academy

Once Upon a Time: 

A Storybook Gala 

Feb. 20

Guests: 246 | $810,306

Grace Place

Celebration of Grace: A Night in Emerald City 

Dec. 7

Guests: 378 | $1,802,156*

Guadalupe Center

Elevate the Dream 

Signature Gala 

Jan. 10

Guests: 315 | $2 million*

Naples Children Foundation

Naples Winter Wine Festival

Jan. 24-26

Guests: 686 | $34 million*

The Village School of Naples

The Knight Gala 

March 29

Guests: 235 | $1 million*

The Shelter for Abused Women & Children

Mending Broken Hearts 

with Hope 

Feb. 18

Guests: 800 | $1,457,793

Women’s Foundation of Collier County

Women Rock Philanthropy Nov. 22

Guests: 600 | $700,000*

Youth Haven

Starry Nights Gala 

March 22

Guests: 500 | $2.5 million*

Total: $50,451,305

ENVIRONMENT ANIMALS 

NATURE

Patty Baker Humane Society Naples

Best in Show Gala 

March 21

Guests: 325 | $1.1 million*

Conservancy of 

Southwest Florida

Magic Under the Mangroves March 6

Guests: 450 | $1.7 million

Naples Botanical Garden

21st Annual Hats in the Garden 

March 28

Guests: 700 | $4.5 million*

Naples Zoo

Zoo Gala 

Nov. 21

Guests: 225 | $1.5 million

Total: $8,800,000

HEALTH

COMMUNITY

American Cancer Society

Bucket List Bash 

Feb. 22

Guests: 310 | $1.5 million*

American Heart Association

Southwest Florida Heart Ball 

March 21

Guests: 550 | $850,000*

Breakthrough T1D 

(formerly JDRF)

An Evening at the Palm Royale 

Jan. 31

Guests: 340 | $1.2 million

David Lawrence Centers 

for Behavioral Health

DLC Sound Minds Signature Event featuring Dennis Quaid 

March 20

Guests: 550 | $1.6 million*

Naples Comprehensive Health

NCH Ball 

March 8

Guests: 480 | $3.1 million*

Neighborhood Health Clinic

Celebration of Hope and Healing Feb. 28

Guests: 165 | $1.7 million*

Planned Parenthood of Southwest and Central Florida

Naples Dinner: 

Care. No Matter What. 

Feb. 13

Guests: 525 | $1,315,678*

STARability Foundation

STAR Gala: Illuminating Abilities 

Feb. 1

Guests: 580 | $3.2 million*

Total: $14,465,678

Grand Total: 

$81,503,486