Miami-Dade County Expeditions

Five Centuries in the Making

Just as removing the modern façade from many structures in downtown Miami will reveal the original architecture from earlier decades hidden beneath, our walking tour of downtown Miami uncovers a riveting past that is often masked by the more modern aspects of this flourishing city. Stroll with us along the pedestrian-friendly sidewalks of this bustling, thriving, many-times-restored urban area.

Step back in time and hear the story of the region’s first inhabitants – the Tequesta Indians – as we begin our walk at the famed and mysterious Miami Circle that overlooks the current Port of Miami on the Miami River. See landmark structures such as the Alfred I DuPont and the Seybold Building. Hear the true and intriguing stories that accompany these sites, such as how over 60 prisoners escaped from the top floors of the Miami Courthouse and how Maurice Gusman saved the majestic Olympia Theater from being demolished. Follow the personal tales of the many different types of people who have moved to Miami chasing fortune or running from hardship.

Although now physically surrounded by a humming commercial center, these stories help us envision how downtown Miami once looked. Occasional Mediterranean-revival and art deco buildings jostling for space with brand-new, high rise luxury condominiums help create the mental picture of an ever-changing Miami. Our adventure through five centuries of Miami’s past draws to an end as we approach the Freedom Tower, Miami’s own Statue of Liberty. History may not be the first thing that comes to mind when exploring the busy streets of one of the most modern cities in the US, but this walking tour leaves guests with a new and surprising perspective of the Magic City.


• All entrance fees and taxes.
• Tour interpretation by guide starts and ends at the hotel.
• Guide to guest ratio does not exceed 1:20.
• Our guides are certified and trained. Inside tour of the atmospheric Olympia Theater at the Gusman Center for the Performing Arts (based on availability).
• A portion of the profits of this tour goesdirectly to support the preservation efforts of the Olympia Theater at the Gusman Center for the Performing Arts.
• Walking tour begins at the Miami Circle and ends near Bayfront Park.
• One non-alcoholic beverage per guest.


• Moderate intensity level.
• A portion of this tour’s profits goes to support the Olympia Theater.
• We recommend this tour for weekdays only.

Contact us

Read more

    • Minimum:
    • 15px
    • Maximum:
    • In one group: 20px
    • Approx._duration:
    • 3-3.5 hours (not including transferfromand tohotel).
    • Time_of_day:
    • Morning or afternoon
    • Meals_included:
    • None (meals can be added for an additional cost).
    • Transportation:
    • To be provided by client or by Dragonfly Expeditions at additional cost.
    • Special notations: