Creativity & the Art of History on Captiva

On Wednesday, January 14, the Captiva Island Historical Society presented Creativity & the Art of History, a unique program held at the Captiva Civic Association. The evening offered attendees an intimate look at the historical context and work-behind-the-works of Captiva resident—artist and author—Ilie Ruby.

Paintings from Ms. Ruby’s latest exhibition were inspired by images drawn from Captiva’s colorful past, many sourced from the CIHS online archives. These archival photographs were transformed by Ms. Ruby into her narrative-driven contemporary style that bridges history with imagination.

CIHS board directors Betty Anholt, Brian Holaway, and Tom Libonate each selected paintings from the exhibition and shared the historical context behind the original images that inspired them. Ms. Ruby then reflected on how history, imagery, and narrative are woven into her creative process.

One painting, She’s a Lady, drew special attention from guest and island icon Ralph Woodring. The work honors his mother, Esperanza Woodring, and her place in the colorful fishing history of both Sanibel and Captiva Islands.

"She's a Lady" - the painting featuring
Esperanza Woodring   

 The painting reflects a story shared by Captain Brian Holaway, who spoke of interviewing fishing guides over the years. Often, after listing the names of men in the profession, they would add, “There’s one more… and she’s a lady.”

That lady was Esperanza Woodring—a respected guide whose skill and presence left a lasting impression.

CIHS board and artist Ilie Ruby with the painting the CIHS purchased to gift to Ralph Woodring  (from the left: Tom Libonate, Brian Holoway, Ms. Ruby, Mary Jane Vinson, Mike Boris)

In a moving moment, the Captiva Island Historical Society surprised Ralph Woodring by acquiring and presenting the painting to him, in recognition of the Woodring family’s deep roots in island history. Ralph then offered a gift of his own to the audience, sharing personal memories of his mother that provided a poignant and colorful glimpse into her life, her work on the water, and the example she set.

The CIHS presents the painting featuring his mother to Ralph Woodring

His remarks, combined with the historic inspiration behind Ilie Ruby’s exhibition, demonstrated how art can bring history to life—creating space for reflection and connecting generations through shared stories.

The gathering underscored the meaningful role the Captiva Island Historical Society plays in celebrating local history through art, conversation, and storytelling that keeps history alive in memorable ways.

Ralph Woodring delights the audience with his colorful personal memories
of his mother and his life on Woodring Point

The CIHS again extends gratitude to Florida Trust Wealth Management, originally The Sanibel Captiva Trust Company, for their support as the season presenting sponsor.

Photos coutesy of Sanibel Star LLC. and CIHS board members

For information and tickets for the full season of CIHS events.

CLICK HERE