In this episode of Icons of Naples, Kristen Weardon welcomes Jacob Winge, a local historian and civic leader whose family roots in Southwest Florida stretch back nearly a century. Jacob provides a vivid look at the evolution of Collier County, from its days as a vast wilderness of 5,000 residents to the interconnected international destination it is today.

Jacob shares the history of his family’s local businesses, including George W. Shepard & Son and his grandfather's specialized fish taxidermy, offering a unique perspective on the industries that first built this community. The conversation explores the distinct identities of Naples' many neighborhoods and serves as a passionate call for long-term vision and community involvement to preserve the "mosaic" of Florida's west coast.

“We want to keep those individual identities...you get a mosaic when every community has its own little color on the board.” — Jacob Winge.

Thank you to our location sponsor, Feel Amazing Spine and Joint Institute, for allowing us to record in their space.

Thank you to our technology sponsor, Robert of Philadelphia, for making this podcast possible.

In this episode of Icons of Naples, Kristen Weardon sits down with Don Hunter, a former Collier County Sheriff, whose leadership helped guide Naples through decades of growth, change, and challenge.

From arriving in Naples as a young boy in the early 1960s to serving over 20 years as Sheriff, Don Hunter shares firsthand stories of how this once small coastal town evolved into one of Florida’s most sought-after communities. This conversation goes beyond history—it’s about leadership, community, public service, and the people who built Naples from the ground up.

What you’ll learn in this episode:

“The Naples proper built upon the good aspects of a social grouping: academics, social awareness, and want to do better.” — Don Hunter.

Thank you to our location sponsor, Feel Amazing Spine and Joint Institute, for allowing us to record in their space.

Thank you to our technology sponsor, Robert of Philadelphia, for making this podcast possible.

Thank you to 239 Live Productions for their editing services.

In this episode of Icons of Naples, Kristen sits down with Dr. Lois Bolin, the woman widely known as the "Old Naples Historian." For nearly 5 decades, Dr. Bolin has dedicated herself to preserving the cultural landscape of Naples, ensuring the community’s heritage isn't lost to the rapid tides of development. From her early days as a competitive tennis player to founding Naples Backyard History, Lois has been at the forefront of how Naples remembers itself.

Lois shares a treasure trove of local "family stories," offering a unique look at the business districts, the philanthropic giants who saved the Naples Pier, and the deep-rooted military history of Southwest Florida. This conversation is an essential guide for anyone who wants to understand the soul of the community beyond the modern skylines.

“History is nothing more than family stories...stories about families that did stuff they ought not to do and family stories about families that did what they were supposed to.” — Dr Lois Bolin.

Thank you to our location sponsor, Ferrari of Naples, for allowing us to record in their space.

Thank you to our technology sponsor, Robert of Philadelphia, for making this podcast possible.

In this episode of Icons of Naples, Kristen Weardon sits down with Garrett Anthony, the spokesperson for one of the city's most respected pioneering families. Arriving in Naples from Alabama in 1953, the Anthony family was among the first Black families to settle in what was then a sleepy fishing village. Garrett shares the powerful story of his great-grandparents, LC ("Big Daddy") and Daisy May ("Big Mom"), who moved south to trade sharecropping for a life defined by honest wages, community service, and - above all - education.

From the establishment of River Park to the naming of Anthony Court and the solemn legacy of Charlie C. Anthony Park, this conversation explores how a close-knit family built a foundation of integrity that has touched nearly every corner of Naples—from our schools and fire departments to our golf courses and neighborhoods.

“Just do right for other people.” — Garrett Anthony.

Thank you to our location sponsor, Ferrari of Naples, for allowing us to record in their space.

Thank you to our technology sponsor, Robert of Philadelphia, for making this podcast possible.

In the conclusion of this special 2-part conversation, Kristen Weardon continues her exploration of Naples with acclaimed artist Paul Arsenault. Having lived a block from the Naples pier for decades, Paul provides an intimate look at the "genteel appreciation" of the town’s early days and the influential figures - from philanthropic giants to "old characters" - who helped shape its history.

Paul reflects on the importance of environmental stewardship, the evolution of local landmarks like Everglades City and Corkscrew Swamp, and his personal mission to preserve the last remaining architectural gems of Old Naples. This episode serves as a powerful call to action to honor the community’s roots while navigating the inevitable tides of development and change.

“If this could be saved, this would be special for the community and for generations.” — Paul Arsenault.

Learn more at ArsenaultGallery.com and check out An Artful History of Naples at ArtfulHistoryOfNaples.com

Thank you to our technology sponsor, Robert of Philadelphia, for making this podcast possible.

In this episode of Icons of Naples, Kristen Weardon sits down with acclaimed artist and preservationist Paul Arsenault. Since arriving in Naples in the 1970s, Paul has dedicated his career to capturing the soul of the community on canvas. From his early days as a deckhand on a research vessel to becoming one of the most recognizable names in the Florida art scene, Paul shares the "primal surge" that drew him to the corkscrew swamp and anchored his life in Naples.

Paul discusses his unique approach to landscape painting, the transition from New England light to tropical color, and his decade-long tradition of capturing Naples' architectural landmarks through his beloved annual calendars. This conversation is a journey through a changing landscape, documented by a man who believes every painting should come with a story.

“If you come back with a painting and a story, it's a real successful day.” — Paul Arsenault.

Learn more at ArsenaultGallery.com and check out An Artful History of Naples at ArtfulHistoryOfNaples.com

Thank you to our technology sponsor, Robert of Philadelphia, for making this podcast possible.

In this episode of Icons of Naples, Kristen Weardon sits down with Kristen Coury, the visionary Founder, CEO, and Producing Artistic Director of the Gulf Shore Playhouse. Arriving in Naples in 2004 from the high-stakes theater worlds of London and New York City, Kristen saw an opportunity to bring professional, Broadway-caliber theater to this arts-loving community.

What began as a one-woman operation with a $0 budget and no employees has blossomed over 20 years into a powerhouse cultural institution. Kristen shares the raw, behind-the-scenes journey of building the Playhouse—from "bootstrapping" productions with $40 outfits from Marshalls to opening a state-of-the-art, multimillion-dollar theater complex. This is a story of manifestation, ruthless passion, and the transformative power of the arts on a city’s economy and soul.

“I do what I do so that the audience can have a life-changing experience...The moment that I quit would be the moment right before there was success.” — Kristen Coury.

Connect with Gulf Shore Playhouse:

For tickets & information, visit GulfshorePlayhouse.org to view upcoming shows and events.

Follow online by connecting with Kristen Coury and the Playhouse on social media for behind-the-scenes content and updates on world premieres.

Thank you to our location sponsor, Gulfshore Playhouse, for allowing us to record in their Founder's Lounge.

Thank you to our technology sponsor, Robert of Philadelphia, for making this podcast possible.

In this episode of Icons of Naples, Kristen sits down with Paul "Butch" Manley, a cornerstone of the Collier County educational system for decades. Known to generations as the first principal of Barron Collier High School, Mr. Manley shares his journey from an Indianapolis teacher to a foundational leader in Naples education, starting in 1967.

The conversation delves into the "frontier" days of local schooling—from teaching biology and coaching track at Naples High to managing the explosive growth that led to double sessions and the opening of multiple new campuses. Mr. Manley reflects on his enduring philosophy that every student is capable of success if their unique needs are understood and supported.

“If you can find out what the problem is, that student can learn. You got to believe that or you shouldn't be a teacher.” — Paul "Butch" Manley.

Thank you to our location sponsor, Ferrari of Naples, for allowing us to record in their space.

Thank you to our technology sponsor, Robert of Philadelphia, for making this podcast possible.

In this episode of Icons of Naples, Kristen Weardon sits down with Tony Ridgway, a pioneering chef and restaurateur who has been a cornerstone of the Naples dining scene since 1971. Tony shares his journey from arriving in a quiet 1962 Naples to becoming a key architect of the city's culinary identity.

Tony reflects on the evolution of "Old Naples," the shift from food-centric to relationship-driven service, and the grit required to navigate decades of growth and change. From the early days of The Chef's Garden to the enduring legacy of Ridgway Bar & Grill, Tony’s story is a testament to the passion and community spirit that defines the Naples experience.

“I recognize that food comes in second. Service and the relationships that we develop with the people is everything.” — Tony Ridgway.

Check out Ridgway Bar & Grill at RidgwayBarAndGrill.com

Thank you to our location sponsor, Feel Amazing Spine and Joint Institute Naples, for allowing us to record in their space.

Thank you to our technology sponsor, Robert of Philadelphia, for making this podcast possible.

In this episode of Icons of Naples, Kristen Weardon welcomes Eileen Arsenault, a dedicated champion of historic preservation, cultural awareness, and environmental conservation. From her early days navigating the quaint, quiet streets of Naples in the 1980s to her deep involvement with the historical society and environmental boards, Eileen shares how she became a steward of the community’s unique character.

Eileen discusses the power of visual history, specifically through her new book, which uses art to anchor the rich narratives of Collier County. She provides a fascinating look at the early pioneers, the importance of preserving natural habitats like mangroves and coral reefs, and the "spirit" of the historic homes that anchor Old Naples today.

“Whatever resonates in their heart about things that should be preserved... I hope they will work towards preserving it.” — Eileen Arsenault.

Check out An Artful History of Naples at ArtfulHistoryOfNaples.com

Thank you to our technology sponsor, Robert of Philadelphia, for making this podcast possible.