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The Chittums Skiffs Story: Adapt, Evolve & Perfect

By Tom Murray

It began as a quest for perfection.

Hal Chittum co-founded Hell’s Bay Boatworks in 1996 because there were no boats in the shallow-water fishing marketplace that came close to satisfying his exacting standards for design and performance.

Just a few years later, more than a thousand Hell’s Bay skiffs were on the water, and the legendary entrepreneur, guide, and boat builder sold the company, as he was justifiably recognized and commended for launching a revolution with a skiff known as the Whipray.

Not one to sit idle, Chittum and renowned captain George Sawley promptly created another company, Chittum Skiffs, and immediately began the task of making Hal’s vision become a reality—a state-of-the-art flats skiff, superior to everything else on the market. And after what Chittum described as nearly a year of “chopping, cutting, adding, removing, de-rigging and re-rigging,” he and his team proudly introduced the Islamorada 18, or as Chittum prefers to call it, “the best damn skiff in the industry.”

Chittum evolution 2024 Jan
Chittum, along with Captain George Sawley, swiftly established Chittum Skiffs to bring Hal’s vision to life—a cutting-edge flats skiff surpassing all others. After nearly a year of intense modifications, they proudly unveiled the Islamorada 18, hailed by Chittum as “the best damn skiff in the industry.”

So while perfection was always the ultimate goal, the success of the Chittum brand is also the result of adapting, evolving, and never being satisfied, while relentlessly striving for constant improvement. That’s consistently been the case during every stage of production in the factory, and now it also applies to the recently invigorated campaign of managing the company through a transition and elevating the exposure of the brand.

This explains the hiring of Stephen Cunningham as CEO of Chittum Skiffs in August 2023. Cunningham has decades of experience as an entrepreneur, launching six start-up companies during his career. However, Cunningham quickly realized that this company and the Chittum brand were different from previous projects he had been involved with. At Chittum, both the reputation of the product and the passion of the personnel for building world-class boats was unlike anything he had experienced.

Chittum Jan2024 Mill and Cunningham
IGFA Trustee Andy Mill, left, engages in discussions with Stephen Cunningham, the CEO of Chittum Skiffs, regarding the specifics of Mill’s upcoming skiff currently in production.

“It is amazing,” Cunningham says, “especially when you consider Chittum has only been around for seven and a half years. Hal and George combined to change the game of boat-building with the first design ever that meets all the needs of the best anglers out there, and the recognition and appreciation are enormous. The inshore angling community has been incredibly supportive of and complimentary about this boat, and it is a privilege to build on that history of innovation.”

Realizing the weight of the brand and the respected clientele using Chittum skiffs, one of the first steps Cunningham took as CEO was the formation of an Advisory Board of captains, which brought together a trio of respected and renowned fly fishing guides—David Mangum, JT Van Zandt, and Dustin Huff. While Chittum had worked closely with respected fishing guides from the start, this official formation solidified the company’s commitment to making the best product possible for the inshore flats aficionado.

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