Key West is full of history and charm and one of the best ways to explore this charming culture is by wandering its streets. From whimsical to historically significant, these street names offer a glimpse into the island's vibrant past. Let's take a fun and informative journey through some of the most interesting street names in Key West.

1. Duval Street
   This is perhaps the most famous street in Key West, stretching from the Gulf of Mexico to the Atlantic Ocean. Named after William Pope Duval, the first territorial governor of Florida, it's the heart of the city's nightlife, shopping, and dining scenes.

2. Fleming Street
   Named after one of Key West's founders, John Fleming, this street is lined with beautiful Victorian homes and lush gardens. It's a quieter street perfect for a leisurely bike ride or a peaceful walk.

3. Petronia Street
   Petronia Street runs through the historic Bahama Village, an area rich in African-American and Bahamian culture. The name reflects the diverse heritage and vibrant community that still thrives here today.

4. Simonton Street
   This street is named after John Simonton, one of the original purchasers of Key West. Its historic inns, art galleries, and old buildings offer a peek into the past.

5. Caroline Street
   Caroline Street is steeped in history and local lore. It’s a great place to find unique shops, local eateries, and historic architecture that tells the story of old Key West.

6. Whitehead Street
   Walking down Whitehead Street feels like taking a step back in time. Named after John Whitehead, another of the island’s early developers, this street is famous for the Ernest Hemingway Home and Museum. 

7. Eaton Street
   Home to the Key West Historic Seaport, where you can find historic ships and a lively marina, Eaton Street is named after the early settler William Eaton. It is always bustling and full of life.

8. Truman Avenue
   This street honors President Harry S. Truman, who spent considerable time at the Little White House in Key West. It’s part of the route to the historic site, where visitors can learn about Truman’s connection to the island.

9. Bahama Street
   Reflecting Key West’s Bahamian heritage, Bahama Street runs through the culturally rich Bahama Village. It’s a vibrant area known for its colorful houses, lively music, and delicious food.

Exploring Key West's streets on foot or by bike is a fantastic way to immerse yourself in the island's unique ambiance. With bike rentals readily available and pedestrian-friendly paths, you can leisurely discover these historic streets and their hidden gems at your own pace. It's an adventure filled with picturesque views, intriguing stories, and delightful surprises around every corner.

Explore with Us!

Exploring Key West through its street names offers a unique and delightful way to connect with the island’s history and culture. Each street tells a story, reflecting the diverse influences that have shaped this tropical paradise. So next time you’re in Key West, take a stroll down these historic streets with an open heart and a curious mind, embracing the unique and unexpected along the way. Curious about seeing it for yourself?

Get your free travel plan here. Happy exploring!