Welcome to the vibrant neighborhoods of Key West, a paradise tucked away at the southernmost tip of the U.S. Our guide will take you through the unique character and charm of each neighborhood, immersing you in the rich culture, stunning architecture, and lush tropical allure that make Key West an unforgettable destination. Discover hidden gems, iconic landmarks, and local favorites as we embark on this journey through the enchanting neighborhoods of Key West.
The best way to see Key West is with Old Town Trolley Tours. You can hop on and off their guided tour, which covers more than 100 points of interest in unique areas like Old Town and Bahama Village. It’s the most flexible and complete way to sightsee, making it the top choice for any visitor.
Old Town Trolley Tours is expertly routed to provide access to every major attraction and neighborhood.
The history of Old Town is as rich and colorful as the district itself. Awash with turn-of-the-century architecture, Old Town is a living history book where every corner tells a story. Named for its historic significance, its streets are lined with notable structures such as the impressive Fort Zachary Taylor and the charming home of Ernest Hemingway, where the author penned some of his most memorable works. It is this authentic fusion of history, culture, and architecture that makes Old Town the best neighborhood for visitors to immerse themselves in on a Key West vacation. Every nook and cranny resonates with tales of the past, offering a unique and unforgettable journey through time.





Bahama Village, with its rich and vibrant history, is an essential part of Key West’s multicultural heritage. In the 19th century, many Bahamians moved to Key West seeking new opportunities, making Bahama Village a symbol of Bahamian influence on the island. The Bahamian immigrants brought with them their unique architectural style, which can be seen in the “shotgun” houses scattered across the neighborhood. Painted in hues of white, Caribbean blue, and canary yellow, these houses are a reflection of the Bahamian spirit and a nod to the area’s Caribbean roots. The Frederick Douglass School, an emblem of the community’s commitment to education and social development, stands proud in this neighborhood, showcasing the community’s resilience and aspiration for progress. For visitors, Bahama Village offers an authentic and immersive experience of Bahamian culture, making it a must-visit neighborhood in Key West. From exploring the colorful “shotgun” houses to visiting the historic Frederick Douglass School, a trip to Bahama Village will leave you with an appreciation for its rich cultural heritage and the enduring Bahamian influence in Key West.

Santiago’s Bodega is a culinary gem that beckons food enthusiasts with its delectable tapas in Key West neighborhoods. Located in the heart of Key West, this restaurant offers a diverse menu featuring an array of small plates, each bursting with unique flavors. From savory bruschettas to succulent seafood and gourmet cheese selections, there’s something to tantalize every palate. The cozy and welcoming atmosphere, coupled with a superb wine and cocktail list, makes Santiago’s Bodega an ideal choice for a memorable dining experience in the Key West neighborhood.
La Creperie French Cafe is a delightful culinary hideaway that brings the flavors of France to Key West neighborhoods. Nestled in Old Town and its neighborhoods, this charming café specializes in crafting delectable crepes that are both sweet and savory. Whether you’re craving a Nutella-filled dessert crepe or a savory crepe with ham and cheese, La Creperie has a wide range of options. Pair your crepe with a café au lait or a glass of French wine for an authentic and cozy French dining experience right in the heart of Key West neighborhoods.

The Historic Seaport has been the lifeblood of Key West’s boating and fishing economy since the 1800s, playing a foundational role in the development of the town. Its allure began to magnetize visitors in the 1940s, stirring interest with its flourishing marine activities and charming seaside appeal. The Seaport underwent notable redevelopment in 1992, transforming it into a vibrant hub that successfully marries its rich past with modern conveniences. Today, it serves as an essential neighborhood for visitors to immerse themselves in the coastal livelihood of Key West. Here, one can witness the daily hustle of fishers, marvel at the grandeur of majestic sailing vessels, and partake in waterfront dining experiences. The Historic Seaport, with its unique blend of tradition and contemporary charm, is an unmissable destination on any Key West vacation itinerary.

Sails to Rails is temporarily closed as we prepare to journey to an exciting new location.

The Turtle Cannery Museum is a testament to Key West’s unique history in the sea turtle industry. Located on the site of an old turtle cannery in Key West neighborhoods, this museum offers visitors a glimpse into the island’s role in processing sea turtles for their meat, shells, and eggs. With informative exhibits and artifacts, you’ll gain insight into this once-thriving but controversial industry and its impact on local wildlife in Key West neighborhoods. The museum serves as a reminder of Key West’s evolving relationship with the environment and conservation efforts in the region.

The Casa Marina area, named after the illustrious Casa Marina Hotel, is a cornerstone of Key West’s historic charm. The prestigious Casa Marina Hotel, constructed in 1920 by American industrialist Henry Flagler, was envisioned as a luxurious retreat for his railroad patrons. The hotel’s illustrious past includes hosting notable guests such as American author Ernest Hemingway and President Harry Truman. During World War II the hotel served as a military base and later played a crucial role during the Cuban Missile Crisis. Today, this residential neighborhood echoes the grandeur of the past, with tree-lined streets and elegant homes. The Casa Marina area’s rich history, coupled with its tranquil ambiance, makes it a must-visit neighborhood for those seeking a glimpse into Key West’s illustrious past. The timeless elegance of the Casa Marina Hotel, coupled with the area’s historical significance, offers visitors a unique opportunity to walk through the pages of Key West’s vibrant history.


The Truman Annex, a distinguished neighborhood with a compelling past, played critical roles throughout history. During World War I, it served as a strategic base, attracting pirates due to its prime location. However, its historical significance doesn’t stop there. From 1945 to 1953, it took on the role of the Winter White House for President Harry S. Truman, marking an important period in American presidential history. Today, the Truman Annex stands as an enduring monument to the past, offering visitors an opportunity to delve into a rich narrative through the Harry S. Truman Little White House Museum. The blend of its historical architecture, tropical ambiance, and compelling past makes the Truman Annex a favorite among visitors, truly encapsulating the essence of a Key West vacation experience.



New Town, a neighborhood in Key West, emerged in the mid-20th century to accommodate the island’s expanding population, making it the residential hub for the majority of Key West’s residents. The development was a strategic move to address the upsurge in residential needs driven by the increasing popularity of Key West as a vacation destination. Characterized by its modern architecture, shopping centers, and residential complexes, New Town offers a contrasting perspective to Key West’s historic charm. It presents visitors with an authentic local experience, highlighting day-to-day life on the island. From bustling restaurants and nightlife to serene parks and recreational facilities, New Town provides a comprehensive Key West experience. Its blend of residential life and vibrant energy makes it an appealing destination for tourists, offering a diverse and enriching vacation experience.

Little Hamaca Park is a charming neighborhood park offering a welcoming and relaxed environment in Key West neighborhoods. Its name, “hamaca,” is Spanish for “hammock,” reflecting the leisurely vibe of this park in Key West neighborhoods. With well-maintained grassy areas, a playground for children, and shaded spots ideal for a family picnic in Key West neighborhoods, Little Hamaca Park is a perfect place for families to spend quality time together and enjoy the outdoors in Key West neighborhoods.

The Key West Golf Club is a golfer’s paradise situated on Stock Island, just minutes away from Key West’s historic district and its neighborhoods. This 18-hole championship course designed by golf legend Rees Jones offers a challenging and picturesque golfing experience in Key West neighborhoods. Surrounded by lush vegetation, lakes, and mangroves in Key West neighborhoods, the course provides a serene and beautiful setting. After your game, relax at the clubhouse, which features a restaurant and bar, or visit the pro shop for golf gear and souvenirs in Key West neighborhoods. Whether you’re a seasoned golfer or a novice, a round of golf at the Key West Golf Club is a fantastic way to enjoy the island’s natural beauty while testing your skills on the links in Key West neighborhoods.

Key West’s neighborhoods, ranging from charming Old Town to vibrant New Town, embody a captivating fusion of history and modernity. This enchanting island destination, with its rich heritage, architectural wonders, and breathtaking landscapes, is an absolute must-visit. Every corner of this paradise promises a truly enriching and unforgettable experience.
Each neighborhood in Key West is a testament to the island’s rich history and diverse culture, and their vibrant energy makes it an unforgettable vacation destination:
Old Town Key West is a historic district boasting quaint architecture, museums, and landmarks that narrate the island’s rich past. In contrast, New Town, developed to accommodate the growing population, is characterized by modern residences, shopping centers, and recreational facilities, offering a glimpse into the local contemporary life of Key West.
The main street in downtown Key West is Duval Street. This bustling strip is renowned for its vibrant nightlife, unique shops, art galleries, and eclectic dining options, encapsulating the true essence of Key West.
Selecting the perfect Key West neighborhood for your stay is a matter of personal preference. Whether you’re seeking vibrant nightlife, historical immersion, or a tranquil escape, Key West has the perfect neighborhood for your stay. Choosing the best area mainly depends on your interests and the Key West experience you desire:
The best way to see all of Key West is by taking the Old Town Trolley Tour. This hop-on, hop-off tour covers major neighborhoods and attractions, providing the flexibility to explore at your own pace.