Key West Conch and Hemingway Self-Guided Walk

Overview

Itinerary

1. 1
   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 Westu2019s refined side and artistic past.

2. 2
   5 min

   This vibrant historic neighborhood reflects the islandu2019s 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.

3. 3
   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.

4. 4
   5 min

   The islandu2019s 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. 5
   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.

6. 6
   5 min

   Once a neighborhood grocery, this laid-back bar evolved into a beloved gathering spot for locals and wandering storytellers. Its unpretentious atmosphere reflects the islandu2019s long tradition of conversation, music, and community.

7. 7
   This modest residence served as President Harry S. Trumanu2019s winter retreat and working office. It stands today as a fascinating link between small-town Key West and world-shaping decisions.

8. 8
   5 min

   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 islandu2019s past.

9. 9
   5 min

   Tucked beside the waterfront, this quiet garden honors writers, pioneers, and leaders connected to the island. Its statues create a reflective space where Key Westu2019s layered history feels close at hand.

10. 10
    Climb to the top of this historic lighthouse for sweeping views over Old Town. Inside, the restored keeperu2019s home reveals the daily life of those who once guided ships through dangerous coastal waters.

11. 11
    5 min

    This famous waterfront plaza is where Key Westu2019s sunset celebration comes alive each evening with performers, artists, and ocean views. By day, itu2019s a relaxed gathering place that captures the islandu2019s playful public spirit.

12. 12
    Built in the early 1800s, this restored Conch-style home offers a rare look at domestic life in Key Westu2019s earliest years. Its tropical gardens and shaded porches preserve the quiet charm of frontier island living.

13. 13
    5 min

    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 Streetu2019s most iconic stops.

14. 14
    5 min

    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.

15. 15
    5 min

    Originally built for military drills and civic events, this sturdy structure speaks to Key Westu2019s strategic coastal role. Today, it stands as a reminder of the islandu2019s mix of defense, community, and adaptation.

16. 16
    This intimate museum celebrates the playwrightu2019s years of work and reflection on the island. Through artifacts and film, it reveals how Key West shaped his creative voice and personal freedom.

17. 17
    5 min

    Housed in the former island armory, this dynamic arts center showcases rotating exhibitions, performances, and workshops. It continues Key Westu2019s long tradition of supporting bold, independent artistic expression.

18. 18
    5 min

    This grand seaside resort opened in 1920 as one of the islandu2019s first luxury destinations. Its sweeping grounds and ocean views mark the moment Key West began redefining itself as a tropical retreat.

19. 19
    5 min

    A quiet, shaded lane named for a local woman of folklore, this street reveals Key Westu2019s softer, more residential charm. Walking here offers a calm contrast to the energy of Duval Street, lined with cottages and island stories.

Good to know

• Public transportation options are available nearby
• Suitable for all physical fitness levels
• Works entirely offline once downloadedu2014no cell service required
• GPS-triggered audio plays automatically based on your location
• Flexible - Buy once, use any day/timeu2014access never expires
• Get the Drives & Detours app download the tour ahead of time

Cancellation policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

• ✓ 100% refund24 hours or more before the start time
• ✕ 0% refundLess than 24 hours before the start time