Isaac Knight — Highwaymen Seascape, Original Oil on Canvas-Board, Sailboat at Sunset, Signed

A luminous and evocative Florida Highwaymen seascape by Isaac Knight (American, 1941–2022) — one of the original members of the celebrated Fort Pierce Highwaymen, the group of self-taught African American landscape painters who in the 1950s and 1960s created a distinctive and now-iconic body of work depicting the Florida landscape. Traveling the highways of the Sunshine State selling their paintings door-to-door and from car trunks, the Highwaymen produced some of the most joyful, vibrant, and genuinely American landscape paintings of the 20th century — and today are recognized as an essential chapter in both Florida art history and American folk and outsider art.

This painting captures the scene Knight returned to again and again throughout his career: a sailboat silhouetted against a blazing orange sunset, with a graceful palm tree arching in the foreground and three birds in flight against the sky. It is the quintessential Highwaymen composition — immediate, optimistic, and painted with the confident, rapid brushwork (and in Knight's case, the distinctive paint knife signature) that defines the movement. Signed with paint knife in the lower right foreground.

Isaac Knight is among the more sought-after of the 26 original Highwaymen painters. His work is held in private collections throughout Florida and has been exhibited in institutional surveys of the movement. Highwaymen paintings have appreciated significantly since the group's rediscovery in the 1990s and their 2004 induction into the Florida Artists Hall of Fame.

• Artist: Isaac Knight (American, 1941–2022)
• Group: Fort Pierce Highwaymen
• Medium: Oil on canvas-board
• Subject: Sailboat in front of bright orange sunset; palm tree in foreground; three birds in flight
• Signature: Signed with paint knife, lower right foreground
• Source: Winter Associates, Inc., Plainville, CT — April 20, 2026 — Lot 217
• Condition: Please review all photographs carefully.

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