Naples Children & Education Foundation Welcomes New Trustees

The Naples Children & Education Foundation (NCEF), founders of the Naples Winter Wine Festival (NWWF), has added Kelley and Jim Bailey and Dena Rae Hancock and P. Robert Caito as Trustees. In this role, they will support NCEF’s vision of making a profound and sustaining difference in the lives of underprivileged and at-risk children in Collier County.

“These new Trustees bring a blend of decades of business, social and civic experience with new and fresh ideas and will be a tremendous asset to our organization moving forward,” said Valerie Boyd, NCEF Chairman of the Board. “Their sincere desire to leave a legacy is not only evident in the volunteer time that they contribute, but also by the generous contributions that they make.”

As co-owners of the beautiful Knights Bridge Winery in Sonoma County, California, Kelley and Jim Bailey share a commitment to excellence and to giving back. Together, they work tirelessly to generously support a wide range of philanthropic endeavors through their foundation.

Kelley and Jim Bailey

Jim had a diverse career, from investment and financial advisor to environmental entrepreneur to vintner. He formed Cambridge Associates in 1973 to provide investment and financial planning services to nonprofit, endowed institutions. His alma mater, Harvard University, was his first client and for almost 50 years since Cambridge Associates has been a leading voice in building institutional-quality portfolios for endowments, foundations, pensions and private clients. Jim also co-founded the Plymouth Rock Co., a New England auto and homeowners’ insurance company.

Combining his passion for wine with farming, Jim and a group of family and friends purchased a 100-acre parcel of land in 2006. Understanding that great wine starts in the vineyard, they adopted new, sustainable vineyard management techniques, replanted portions of the estate and hired a team of seasoned professionals who shared their ambition to produce the best wines possible.

A New York native, Kelley Bailey began her career in wine early on. Her first introduction to the industry started in 1987 at Bridgehampton Winery on Long Island. After a few years, she moved to Northern California with another small winery, and in 1993 Kelley began working with Jackson Family Wines. In 2007, she became Executive Vice President of Marketing, working closely with Jess Jackson and Barbara Banke, spearheading marketing strategy and brand development across the company portfolio. In 2011, she was named President of the Spire Collection, the company’s portfolio of luxury wines. She managed all strategy and development in her role, including brand marketing, national sales, direct-to-consumer, hospitality and culinary.

With more than three decades of wine industry experience, Kelley brings exceptional vision and expertise to help shape the future of Knights Bridge Winery. In 2020, Kelley and Jim embarked on a long-awaited project to build a winery on the estate where they are now making wine and welcoming their first visitors. The winery, designed by world-renowned architects Howard Backen and John Taft of Backen & Gillam, is the second-ever built in Knights Valley and its construction is the culmination of nearly a decade of thoughtful planning and designing.

Dena Rae Hancock & P. Robert Caito

Dena Rae Hancock and P. Robert Caito have made Naples their full-time home since 2017. Dena Rae is Senior Vice President for Wealth Services at The Naples Trust Company. Most of her professional career has been with the philanthropic community with institutions serving children and education missions, most recently as CEO of the Golisano Children’s Museum of Naples. She also served as Vice President of Institutional Advancement at Marian University in Indianapolis, Indiana.

Rob’s career includes 27 years in multiple leadership roles in his family’s fresh-foods distribution company prior to its acquisition in 2016 and eight years managing a fundraising distribution company that he and Dena Rae established before its acquisition in 2008. Rob currently is managing a growing network of private equity firms.

Dena Rae and Rob have been and continue to be involved with many philanthropic organizations both in Naples and their home state of Indiana, including the Children’s Museum of Naples(where they currently are serving as co-chairs of the 2023 Night at the Museum gala) and the Indiana University Foundation Board. They also founded the Hancock Hiltunen Caito Center for Leadership and Life Skills for the Indiana University Athletics’ Circle of Excellence.

About Naples Children & Education Foundation

The Naples Children & Education Foundation, the founding organization of the Naples Winter Wine Festival, is improving the educational, emotional and health outcomes of underprivileged and at-risk children. Through its annual grants and strategic initiatives, NCEF has impacted more than 50 of the most effective nonprofits in the local community, providing more than 275,000 children with the services and resources they need to excel. NCEF’s unique approach, which emphasizes collaboration between organizations and bridges public and private resources, has become a blueprint for how to transform a community, one issue at a time.

About Naples Winter Wine Festival

The Naples Winter Wine Festival, one of the world’s most prestigious charity wine auctions, offers a weekend of unforgettable memories. Guests enjoy world-class food and wine during intimate dinners in private homes and are invited to bid on once-in-a-lifetime travel and wine experiences during an electrifying live auction. Since its inaugural event in 2001, the NWWF has raised nearly $244 million, making a profound difference in the lives of hundreds of thousands of children. The NWWF will return to The Ritz-Carlton Golf Resort, Naples on February 3-5, 2023.

For additional information on the Naples Children & Education Foundation or the Naples Winter Wine Festival, contact Lisa Juliano at or 239-514-2239.


0 replies

Leave a Reply

Want to join the discussion?
Feel free to contribute!

Leave a Reply

Your email address will not be published.