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Monticello Self-Guided Walking Tour

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  • Destin
  • Updated November 2, 2026

Explore Monticello’s historic district on a self-guided audio walk through the town’s frontier roots, statehood, and Civil War-era history.

About this tour

Walk through Monticello’s preserved historic district and follow the story of a Florida frontier town as it grew into a thriving cotton-shipping center. This self-guided Monticello Walking Tour begins at Courthouse Circle, the town’s political and social heart in the 1840s, where residents learned Florida had become a state in 1845.

As you explore at your own pace, hear the story of Mary Adeline Walker and her husband William, central figures in the Palmetto Pioneers book series. Discover how settlers known as Palmetto Pioneers, many with roots in South Carolina, shaped the community. The tour also examines Jefferson County’s political influence and how its large enslaved population contributed to its support for secession.

Use the app’s audio, maps, and geodata, with offline access available. Install the app and enter the code on your confirmation ticket before you arrive; directions guide you to the starting point, and the tour begins when you reach it. Set out to uncover the stories behind Monticello’s historic streets on this flexible Monticello Walking Tour.

Highlights

  • Trace Monticello’s transformation from frontier settlement to cotton-shipping town
  • Follow the story of Mary Adeline Walker and William
  • Explore the preserved historic district and Courthouse Circle
  • Learn how Florida statehood and secession shaped Jefferson County

What's included

Included

  • Lifetime access to the English tour before and after your booking date
  • Offline access to audio, maps, and geodata
  • Android and iOS app
  • Self-guided GPS tour with flexible pacing
  • Directions to the starting point and automatic tour start

Not included

  • Smartphone
  • Headphones

Ratings on each provider

The ratings and review counts each booking site shows for this tour.

Important information

  • Install the mobile app and enter the code from your confirmation ticket before arrival
  • Starting point: parking lot at the corner of E Washington and Courthouse Circle
  • Detailed starting point instructions are available in the app
  • Public transportation options are available nearby
  • Suitable for all physical fitness levels

How this score is calculated

This tour has no TourTruth score yet: Viator doesn't show a usable rating for it. It gets a score as soon as a provider lists one.

How the score works
  • Each provider rating is turned into a percentile: the share of that provider's ratings it beats, weighted by review counts.
  • Listings on different providers are combined in proportion to their review counts.
  • Tours with few reviews are pulled toward the average until more reviews come in, so a handful of perfect reviews can't top the list.
  • The result is shown from 0 to 10. Tours without a usable provider rating are not scored.

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