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Offered languages
- English
- English
Explore the vibrant spirit of the Florida Keys with the Key West Conch and Hemingway Walk.
This self-guided adventure immerses you in the rich tapestry of island life where writers like Ernest Hemingway and Tennessee Williams found their muse.
Navigate through charming streets, lively bars, and historic neighborhoods that showcase the unique blend of Caribbean, Cuban, and Conch cultures.
As you stroll at your own pace, engaging audio narratives reveal tales of resilience, creativity, and community that define this iconic island.
Discover the essence of Key West, where every corner invites you to pause, reflect, and connect with its storied past.
What's Included
Meeting and pickup
Mallory Square can be found on Wall Street. It is the location of the cruise ship docks in Key West.
Sloppy Joe's Bar is on Duval Street, near Mallory Square. It is on the corner of Greene Street.
Itinerary
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(Pass by)
Step into a graceful 19th-century home filled with period furnishings and surrounded by lush tropical gardens alive with native birds and careful landscaping. This peaceful oasis offers a glimpse into Key West’s refined side and artistic past.
Admission ticket free -
1
This vibrant historic neighborhood reflects the island’s deep Bahamian roots through colorful homes, Caribbean influences, and a strong sense of community. Walking here reveals a side of Key West shaped by working families, faith, and culture.
5 minutes • Admission ticket free -
(Pass by)
A classic Key West sight, this open-air train has carried visitors through the Old Town for decades. Its cheerful presence is a reminder of how the island transformed local storytelling into a shared visitor experience.
Admission ticket free -
2
The island’s most famous thoroughfare buzzes with music, colorful storefronts, historic bars, and shaded corners. Stretching from the Gulf to the Atlantic, it captures the lively rhythm that defines Key West life.
5 minutes • Admission ticket free -
(Pass by)
Set behind a high coral wall, this elegant Spanish Colonial home is where Ernest Hemingway wrote some of his most famous works. The peaceful gardens and legendary six-toed cats make this a stop full of quiet inspiration and literary history.
Admission ticket free -
3
Once a neighborhood grocery, this laid-back bar evolved into a beloved gathering spot for locals and wandering storytellers. Its unpretentious atmosphere reflects the island’s long tradition of conversation, music, and community.
5 minutes • Admission ticket free -
(Pass by)
This modest residence served as President Harry S. Truman’s winter retreat and working office. It stands today as a fascinating link between small-town Key West and world-shaping decisions.
Admission ticket free -
4
Resting above sea level, this historic cemetery tells the story of storms, shipwrecks, epidemics, and colorful island lives. Humorous and heartfelt epitaphs offer a surprisingly personal window into the island’s past.
5 minutes • Admission ticket free -
5
Tucked beside the waterfront, this quiet garden honors writers, pioneers, and leaders connected to the island. Its statues create a reflective space where Key West’s layered history feels close at hand.
5 minutes • Admission ticket free -
(Pass by)
Climb to the top of this historic lighthouse for sweeping views over Old Town. Inside, the restored keeper’s home reveals the daily life of those who once guided ships through dangerous coastal waters.
Admission ticket free -
6
This famous waterfront plaza is where Key West’s sunset celebration comes alive each evening with performers, artists, and ocean views. By day, it’s a relaxed gathering place that captures the island’s playful public spirit.
5 minutes • Admission ticket free -
(Pass by)
Built in the early 1800s, this restored Conch-style home offers a rare look at domestic life in Key West’s earliest years. Its tropical gardens and shaded porches preserve the quiet charm of frontier island living.
Admission ticket free -
7
Made famous by Ernest Hemingway, this legendary bar has been a lively crossroads for sailors, writers, and travelers for nearly a century. Its bustling energy and historic character make it one of Duval Street’s most iconic stops.
5 minutes • Admission ticket free -
8
With its distinctive coral-pink exterior, this grand 19th-century mansion stands just steps from the Atlantic. It reflects the wealth and ambition that once flowed through Key West during its maritime heyday.
5 minutes • Admission ticket free -
9
Originally built for military drills and civic events, this sturdy structure speaks to Key West’s strategic coastal role. Today, it stands as a reminder of the island’s mix of defense, community, and adaptation.
5 minutes • Admission ticket free -
(Pass by)
This intimate museum celebrates the playwright’s years of work and reflection on the island. Through artifacts and film, it reveals how Key West shaped his creative voice and personal freedom.
Admission ticket free -
10
Housed in the former island armory, this dynamic arts center showcases rotating exhibitions, performances, and workshops. It continues Key West’s long tradition of supporting bold, independent artistic expression.
5 minutes • Admission ticket free -
11
This grand seaside resort opened in 1920 as one of the island’s first luxury destinations. Its sweeping grounds and ocean views mark the moment Key West began redefining itself as a tropical retreat.
5 minutes • Admission ticket free -
12
A quiet, shaded lane named for a local woman of folklore, this street reveals Key West’s softer, more residential charm. Walking here offers a calm contrast to the energy of Duval Street, lined with cottages and island stories.
5 minutes • Admission ticket free
Additional info
- Public transportation options are available nearby
- Suitable for all physical fitness levels
- Works entirely offline once downloaded—no cell service required
- GPS-triggered audio plays automatically based on your location
- Flexible - Buy once, use any day/time—access never expires
- Get the Drives & Detours app download the tour ahead of time
Tags
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
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Cancellation Policy
- For a full refund, you must cancel at least 24 hours before the experience’s start time.
- If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
- Any changes made less than 24 hours before the experience’s start time will not be accepted.
You can cancel up to 24 hours in advance of the experience for a full refund.
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