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Where History, Nature, and Craftsmanship Meet

From Roots to Roads celebrates the living history of Key West, guiding guests through hidden gardens, historic streets, and the island’s craftsmanship.

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Discover Hidden Gardens & Historic Streets

Tropical Roots Walk

Explore lush gardens and native plant life while uncovering the island’s botanical story.

  • July 20, 10:00 AM
  • 90 min
  • 10 people

Historic Streets Discovery

Walk through iconic streets and discover the architecture, culture, and hidden details of Key West.

  • July 20, 10:00 AM
  • 90 min
  • 10 people

Private Tour Experience

Wander through shaded pathways, discover tucked-away spaces, and connect more deeply with the island’s roots, craftsmanship, and evolving story. This is Key West experienced in a more personal, relaxed, and immersive way.

  • July 20, 10:00 AM
  • 2 hr
  • 10 people

What Makes Our Walks Unique

Features

Local Expertise

Led by a local guide sharing the island’s hidden botanical and historic gems.

Small, Relaxed Groups

Enjoy an intimate walk designed for conversation and discovery.

Nature & Storytelling

Experience vegetation, architecture, and culture woven into one journey.

Gentle Scenic Routes

Easy-paced strolls through shaded streets and lush gardens.

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Keywest Florida

But I must explain to you how all this mistaken idea of denouncing pleasure and praising pain was born and I will give you a complete account of the system, and expound the actual teachings

Meet-Up Location

Conveniently located in the heart of Old Town Duval St & Fleming St · Key West

What Our Guests Say

“Keila was an incredible guide—her knowledge of the island’s history, culture, and natural surroundings brought everything to life. It felt very personal, intentional, and deeply connected to the spirit of Key West. One of the most meaningful experiences of our trip.”

“Exploring with Keila felt effortless. She created such a welcoming, relaxed atmosphere while sharing stories that made us see the island in a completely different way. You can feel her passion in every detail—it’s more than a walk, it’s a perspective shift.”

“Keila has a way of making you slow down and really take in your surroundings. Her knowledge, her energy, and the way she guides you through the island make the experience feel unique and memorable. It’s something I’d recommend to anyone wanting to truly connect with Key West.”

Ready to Explore?

Reserve your walk today and experience Key West like never before.

Public Cultural Walking Tour

$55 per person 90 minutes

Explore the heart and history of Key West through a guided walking experience filled with local culture, hidden gems, and storytelling. Perfect for first-time visitors looking to connect with the island.

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Private Tour Experience

$120 per person · 2hrs 2-person minimum

Enjoy a more personal and relaxed version of our signature tour. With a slower pace, deeper storytelling, and time for photos and questions, this experience is designed for those who want a more intimate connection to Key West.

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Custom Roots Experience

$140 per person · 2hrs 2-person minimum

A fully personalized experience built around your interests. From hidden local spots to cultural highlights and photo-worthy moments, this tour is tailored to your pace and preferences for a truly one-of-a-kind experience.

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