Tim Stockwell, a former global executive who once managed teams and facilities in 65 countries, has found a new calling in Key West. After a career of extensive international travel, Stockwell and his wife Kathleen moved to a houseboat in Key West in July 2019.

An Unexpected Contest

Stockwell's Key West adventure took an unexpected turn when he was mistaken for a participant in Sloppy Joe's annual “Papa” Hemingway Look-Alike Contest. Unaware of the event saluting Ernest Hemingway, Stockwell was intrigued and decided to enter. He competed for several years, enjoying the camaraderie among the contestants.

“The Hemingway Look-Alike Society has been an absolute dream, because it’s got such great camaraderie and family focus,” Stockwell told the Keys Weekly. “You make friends. I think the real magical part is the camaraderie around two causes: honoring the name and image of Ernest Hemingway, and the ability to be incredibly generous with a town that is like no other.”

In 2025, Stockwell achieved a significant milestone by winning the contest, becoming the first Key West resident to hold the title since 1999.

Giving Back to the Community

Beyond the contest, Stockwell has become deeply involved in the Hemingway Look-Alike Society. This organization focuses on raising scholarship funds for students attending the College of the Florida Keys. To date, the society has awarded over $350,000 in scholarships. The group also supports local Florida Keys nonprofits, a Cuban youth baseball league inspired by Hemingway, and other individuals in need.

Stockwell's commitment to community extends further. He serves as an ambassador for the College of the Florida Keys and holds the position of vice-president on the board of the Sloppy Joe’s Foundation. This foundation directs its support towards local nonprofits in the arts and community sectors.

Embracing Houseboat Living and Key West's Charm

Stockwell described his houseboat living experience as incredible, highlighting his location on a floating dock with unobstructed views of the water and sunsets. He plans to eventually return to family and executive business coaching but currently cherishes sharing experiences with his wife, Kathleen, and their family.

His enjoyment of the Keys includes diving, biking around Key West, and appreciating the simplicity and beauty of his current lifestyle. Stockwell finds Key West's atmosphere particularly appealing, noting its laid-back nature and the acceptance of its residents.

“What’s fascinating to me about Key West is that nobody cares who you are, what you have or don’t have, or what you’re running from or running to,” Stockwell shared. “If you’re here and you want to have a good time, that’s what it’s all about; just be kind to people. It’s still one of the most laid-back places in the U.S. I love that atmosphere — and, of course, the characters.”

Stockwell, now a prominent figure as the reigning look-alike winner, acknowledges his own role as one of Key West's unique characters.

For more information on local news and real estate, visit Keys Weekly.