Key West Conch and Hemingway Self-Guided Walk
Drives & Detours
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.
Departure Point
- Mallory Square can be found on Wall Street. It is the location of the cruise ship docks in Key West.
Return Details
- Sloppy Joe's Bar is on Duval Street, near Mallory Square. It is on the corner of Greene Street.
Duration
2 hours - 2 hours and 30 minutes
Languages Available
- Audio guide - English
- Printed guide - English
- Audio guide - Spanish
- Printed guide - Spanish
Points of Interest
Stop At: Audubon House & Tropical Gardens
205 Whitehead St, , Key West, Florida
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.
Duration: Not Available
Stop At: Conch Train Tour
303 Front Street, Key West, FL 33040
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.
Duration: 5 minutes
Stop At: Duval Street
Key West, Florida
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.
Duration: Not Available
Stop At: The Ernest Hemingway Home and Museum
907 Whitehead Street, Key West, Florida
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.
Duration: 5 minutes
Stop At: Truman Little White House
111 Front St, Naval Air Station , Key West, Florida
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.
Duration: Not Available
Stop At: Key West Cemetery
701 Pauline Street, Key West, Florida
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.
Duration: 5 minutes
Stop At: Mallory Square
400 Wall St, , Key West, Florida
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.
Duration: Not Available
Stop At: The Oldest House Museum & Garden
322 Duval St, Key West, Florida
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.
Duration: 5 minutes
Stop At: Sloppy Joe's
201 Duval Street, Key West, FL 33040
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.
Duration: 5 minutes
Stop At: Southernmost House Key West
1400 Duval Street, Key West, FL 33040
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.
Duration: Not Available
Stop At: The Historic Armory
600 White Street, Key West, FL 33040
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.
Duration: 5 minutes
Stop At: The Studios of Key West
533 Eaton Street, , Key West, Florida
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.
Duration: Not Available
Stop At: Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street, Key West, FL 33040
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.
Duration: 5 minutes
Stop At: Key West Lighthouse and Keeper's Quarters Museum
938 Whitehead St, , Key West, Florida
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.
Duration: 5 minutes
Stop At: Key West Historic Memorial Sculpture Garden
401 Wall St, , Key West, Florida
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.
Duration: 5 minutes
Stop At: Green Parrot Bar
601 Whitehead St, , Key West, Florida
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.
Duration: Not Available
Stop At: Tennessee Williams Museum
513 Truman Ave, Near Duval St, Key West, Florida
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.
Duration: 5 minutes
Stop At: Bahama Village
Key West, FL 33040
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.
Duration: 5 minutes
Stop At: Angela Street
Angela Street, Key West, FL 33040
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.
Duration: 5 minutes
Additional Information
- 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
- Flexible Usage (unlimited access)
- Audio Guide
- App and Tour Download
Exclusions
- Smartphone (bring your own)
Redemption Instructions
IMPORTANT – YOUR ACCESS CODE IS: DHL916 - PLEASE READ STEPS BELOW -
To access your tour, you’ll need the Drives & Detours App. We recommend downloading the tour in advance in case cell service is unreliable.
DOWNLOAD THE APP:
iPhone: https://apps.apple.com/us/app/drives-detours/id6443681888
Android: https://play.google.com/store/apps/details?id=com.mytoursapp.android.app6506
UNLOCK YOUR TOUR:
1. Open app, tap "Walking Tours", then "Key West Conch and Hemingway Self-Guided Walk"
2. Enter Your Access Code (on iPhone tap "Login to Download" then "Login")
3. Tap "Download Tour" and wait until complete (1-2 minutes)
STARTING THE TOUR:
1. Open app, select your tour
2. Go to start location shown
3. Tap “Start Tour”
ADDITIONAL NOTES:
Tour is valid for 180 days, no need to reschedule
Questions? TEXT us at 619.324.9920
Voucher Info
Mobile or paper ticket accepted
The tour identified in this promotion is made available through Viator. Groupon is not affiliated with or sponsored by the Drives & Detours in connection with this deal. Please contact Groupon customer service for all inquiries related to this offer. Inquiries placed to Viator will be directed back to Groupon.
This offer is not eligible for promo codes.
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.
Departure Point
- Mallory Square can be found on Wall Street. It is the location of the cruise ship docks in Key West.
Return Details
- Sloppy Joe's Bar is on Duval Street, near Mallory Square. It is on the corner of Greene Street.
Duration
2 hours - 2 hours and 30 minutes
Languages Available
- Audio guide - English
- Printed guide - English
- Audio guide - Spanish
- Printed guide - Spanish
Points of Interest
Stop At: Audubon House & Tropical Gardens
205 Whitehead St, , Key West, Florida
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.
Duration: Not Available
Stop At: Conch Train Tour
303 Front Street, Key West, FL 33040
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.
Duration: 5 minutes
Stop At: Duval Street
Key West, Florida
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.
Duration: Not Available
Stop At: The Ernest Hemingway Home and Museum
907 Whitehead Street, Key West, Florida
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.
Duration: 5 minutes
Stop At: Truman Little White House
111 Front St, Naval Air Station , Key West, Florida
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.
Duration: Not Available
Stop At: Key West Cemetery
701 Pauline Street, Key West, Florida
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.
Duration: 5 minutes
Stop At: Mallory Square
400 Wall St, , Key West, Florida
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.
Duration: Not Available
Stop At: The Oldest House Museum & Garden
322 Duval St, Key West, Florida
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.
Duration: 5 minutes
Stop At: Sloppy Joe's
201 Duval Street, Key West, FL 33040
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.
Duration: 5 minutes
Stop At: Southernmost House Key West
1400 Duval Street, Key West, FL 33040
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.
Duration: Not Available
Stop At: The Historic Armory
600 White Street, Key West, FL 33040
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.
Duration: 5 minutes
Stop At: The Studios of Key West
533 Eaton Street, , Key West, Florida
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.
Duration: Not Available
Stop At: Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street, Key West, FL 33040
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.
Duration: 5 minutes
Stop At: Key West Lighthouse and Keeper's Quarters Museum
938 Whitehead St, , Key West, Florida
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.
Duration: 5 minutes
Stop At: Key West Historic Memorial Sculpture Garden
401 Wall St, , Key West, Florida
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.
Duration: 5 minutes
Stop At: Green Parrot Bar
601 Whitehead St, , Key West, Florida
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.
Duration: Not Available
Stop At: Tennessee Williams Museum
513 Truman Ave, Near Duval St, Key West, Florida
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.
Duration: 5 minutes
Stop At: Bahama Village
Key West, FL 33040
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.
Duration: 5 minutes
Stop At: Angela Street
Angela Street, Key West, FL 33040
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.
Duration: 5 minutes
Additional Information
- 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
- Flexible Usage (unlimited access)
- Audio Guide
- App and Tour Download
Exclusions
- Smartphone (bring your own)
Redemption Instructions
IMPORTANT – YOUR ACCESS CODE IS: DHL916 - PLEASE READ STEPS BELOW -
To access your tour, you’ll need the Drives & Detours App. We recommend downloading the tour in advance in case cell service is unreliable.
DOWNLOAD THE APP:
iPhone: https://apps.apple.com/us/app/drives-detours/id6443681888
Android: https://play.google.com/store/apps/details?id=com.mytoursapp.android.app6506
UNLOCK YOUR TOUR:
1. Open app, tap "Walking Tours", then "Key West Conch and Hemingway Self-Guided Walk"
2. Enter Your Access Code (on iPhone tap "Login to Download" then "Login")
3. Tap "Download Tour" and wait until complete (1-2 minutes)
STARTING THE TOUR:
1. Open app, select your tour
2. Go to start location shown
3. Tap “Start Tour”
ADDITIONAL NOTES:
Tour is valid for 180 days, no need to reschedule
Questions? TEXT us at 619.324.9920
Voucher Info
Mobile or paper ticket accepted
The tour identified in this promotion is made available through Viator. Groupon is not affiliated with or sponsored by the Drives & Detours in connection with this deal. Please contact Groupon customer service for all inquiries related to this offer. Inquiries placed to Viator will be directed back to Groupon.
This offer is not eligible for promo codes.
Need To Know Info
For a full refund, cancel at least 24 hours in advance of the start date of the experience.
Merchant is solely responsible to purchasers for the care and quality of the advertised goods and services. Offer is not eligible for our promo codes or other discounts. Learn about Strike-Through Pricing and Savings