Top Destin Walking Tours

Monticello’s homes and historic streets tell the story of a small Southern town’s journey from an optimistic frontier settlement to the Civil War. On this self-guided walking tour, you’ll follow the true story of Mary Adeline Walker and her husband William (central characters in the Palmetto Pioneers book series) through Monticello’s remarkably preserved historic district. The tour begins at the Jefferson County Courthouse Circle, the political and social heart of 1840s Monticello, where citizens first learned Florida had achieved statehood in 1845. As you walk, you’ll discover how Jefferson County became one of Florida’s political centers and how its position as one of the state’s largest slave-holding counties influenced its swift support for secession. Throughout the journey, you’ll learn how Monticello’s early settlers, nicknamed “Palmetto Pioneers“ for their South Carolina origins, transformed a Florida frontier outpost into a thriving cotton-shipping town.