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.
Old Town Trolley Tours
Unveil the magic of Key West’s diverse neighborhoods aboard the Old Town Trolley (OTT) Tours. Our hop-on, hop-off service allows you to navigate the city at your leisure, revealing hidden treasures, architectural marvels, and rich history. Let our knowledgeable team guide you through an insightful journey across Key West’s unique neighborhoods. With the Key West Neighborhoods guide, you can delve into the vibrant culture, tropical allure, and stunning landscapes that define this paradise. Don’t just visit, truly absorb what Key West has to offer with OTT. Secure your journey with us and permit us to cast a light on the enchanting allure of the utmost southern point of the U.S. for your pleasure.
Old Town History
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.
Things To Do in Old Town
The Hemingway Home & Museum, a Spanish Colonial-style house, is a treasure trove brimming with Hemingway’s life relics. Here, you can admire the writer’s original furnishings, rare photographs, and personal memorabilia that paint an intimate picture of his life. Hemingway’s office, where he penned some of his legendary works, remains untouched, providing a glimpse into his creative world. Don’t forget to play with the 40+ polydactyl (six-toed) cats, the descendants of Hemingway’s own cat, Snow White. A stroll around the museum’s lush gardens is a must, where a tranquil pool, Hemingway’s first in Key West, beckons visitors.
Duval Street is the vibrant heartbeat of Key West, alive with a unique blend of historical charm and modern allure. This lively street is a hub for shopping, dining, and entertainment. Discover a plethora of boutique shops offering unique island treasures, or take a break at one of the many sidewalk cafes perfect for people-watching. As the sun sets, the street transforms into a hot spot of nightlife, fueled by live music and tropical cocktails. Don’t forget to experience the famed “Duval Crawl,” hopping from one lively bar to another. A trip to Key West isn’t complete without a stroll down Duval Street.
Mallory Square is the epicenter of Key West’s vibrant neighborhoods. Every evening, locals and visitors alike gather at this historic waterfront square to witness breathtaking views of the Key West neighborhood. This daily ritual is accompanied by a lively street performance scene, featuring talented artists, musicians, and entertainers. Explore the multitude of unique shops and stalls, or enjoy a meal at the nearby restaurants. Mallory Square is a must-visit destination for anyone seeking the true essence of Key West’s communal spirit and its unparalleled neighborhood views.
The Key West Aquarium offers a captivating aquatic experience for visitors of all ages. As one of Florida’s oldest aquariums, it provides an opportunity to get up close and personal with marine life native to the Florida Keys and the Key West neighborhood. Explore the touch tanks to feel the various sea creatures, including conchs. The aquarium’s knowledgeable staff conducts informative and engaging presentations, making it both fun and educational. Kids and adults alike will enjoy learning about the diverse ecosystems surrounding Key West neighborhoods. It’s a family-friendly attraction that’s both entertaining and enriching.
Embark on a historical journey through the heart of Key West with the Conch Tour Train. This charming and informative tour allows you to explore the island’s most iconic landmarks, rich history, and local legends in the Key West neighborhood. As you ride through the charming streets of Old Town and its neighborhoods, you’ll pass by notable sites like the Hemingway Home, Southernmost Point, and Mallory Square. The entertaining narration by friendly engineers makes this a great way to learn about Key West’s heritage while enjoying a comfortable and leisurely ride.
Bahama Village History
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.
Things To Do in Bahama Village
Immerse yourself in the eclectic charm of Blue Heaven, an iconic restaurant nestled in the heart of Bahama Village. This eatery, known for its succulent lobster benedict and Key lime pie, is a gastronomic delight. Surrounded by lush foliage, the outdoor dining area creates a serene atmosphere for guests. Look for the roaming chickens and cats, a quirky feature adding to the restaurant’s unique character. Art lovers will appreciate the on-site gallery featuring local artists. Just steps away, explore the vibrant Petronia Street, brimming with boutiques and galleries, exhibiting the rich culture of 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.
Explore the vibrant Bahama Village Market, a bustling hub known for its eclectic collection of goods. Wander through stalls overflowing with locally made crafts, vintage treasures, and organic produce, reflecting the island’s cultural diversity. Be sure to try a slice of the legendary Key lime pie, a local favorite. Nearby, explore the unique art galleries exhibiting the works of local artisans. Whether you’re shopping for souvenirs or sampling local delicacies, the Bahama Village Market is a must-visit, offering a genuine slice of Key West’s cultural tapestry.
Historic Seaport History
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.
Things To Do in Historic Seaport
The Yankee Freedom III, a high-speed ferry, offers a mesmerizing journey to the Dry Tortugas National Park, a remote island brimming with stunning coral reefs and diverse marine life. Visitors can explore Fort Jefferson, a 19th-century fortress that is a testament to the region’s rich history. The journey onboard allows you to soak up breathtaking oceanic views. While on the island, you can engage in snorkeling, bird-watching, or simply enjoy lunch. The Yankee Freedom III experience is an essential addition to any Key West itinerary, promising a unique blend of history, nature, and adventure.
Visit Key West’s maritime heritage at the Sails to Rails Museum. Wander through a world of shipwrecks and treasure hunting, learning about Key West’s history as a prosperous trading port. Stand in awe of the intricate model ships and delve into stories of fabled pirates and sea battles. From the Age of Sail to the arrival of the railroad, the Sails to Rails Museum gives visitors an immersive journey through the key historical milestones that shaped Key West.
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.
Fury Water Adventures offers an exciting range of aquatic activities for adventure seekers in Key West neighborhoods. From snorkeling in the pristine waters of the Florida Keys to thrilling parasailing experiences, Fury Water Adventures has something for everyone in Key West neighborhoods. Choose from catamaran cruises, glass-bottom boat tours, jet ski rentals, kayaking excursions, and more. With a professional and friendly staff, top-notch equipment, and a commitment to safety, you can embark on a memorable aquatic adventure while soaking up the natural beauty of Key West.
History of the Casa Marina Area
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.
Things To Do in Casa Marina
The Casa Marina Hotel is the epitome of Key West’s historic charm. Be sure to take a leisurely walk or bike ride along its oceanfront, offering breathtaking views of the sea. A must-see is the meticulously maintained Casa Marina Gardens, a serene haven of lush greenery and blooming flowers. Discover hidden corners of tranquility while enjoying the shade of towering palm trees. The hotel’s architectural grandeur, coupled with its picturesque surroundings, makes it an essential visit on a Key West itinerary, immersing visitors in the rich history and serene beauty of the area.
The Southernmost Point, an iconic landmark in Key West, is a mere 90 miles from Cuba. This brightly painted buoy is a must-visit, marking the continental U.S.’s most southern point. Capture memorable photos at this iconic spot that symbolizes the endearing spirit of Key West. Just a stone’s throw away, enjoy local cuisine at vibrant food stands or explore the nearby Key West Butterfly and Nature Conservatory for a dose of Key West’s natural beauty. No visit to Key West is complete without a stop at the Southernmost Point; it’s a touch of immortality on your tropical journey.
Truman Annex 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.
Things To Do in the Truman Annex
Fort Zachary Taylor State Park Beach is a historic gem nestled in Key West. This state park is renowned for its mid-19th-century fort, a well-preserved piece of masonry architecture. Visitors can explore the fort’s labyrinthine layout, displaying a fascinating mix of turn-of-the-century architecture and military history. In addition to its historical allure, the park offers a pristine beach for sunbathing and picnicking. Its clear waters are perfect for snorkeling, offering a peek into its vibrant marine life. A walk through the park’s nature trails reveals a variety of local flora and fauna, making the Fort Zachary Taylor State Park Beach a must-visit for history buffs and nature lovers alike.
The Truman Little White House, once the winter retreat of President Harry Truman, today stands as a museum, immersing visitors in a rich political past. Here, you can explore rooms preserved in their original 1940s décor, peruse artifacts from Truman’s tenure, and learn about the consequential decisions made within these walls. Don’t miss the botanical garden, a tranquil oasis marked with informative plaques about the house’s history. This site captures an important fragment of American history, making it a must-visit location in Key West.
Truman Waterfront Park, a scenic and expansive green space, offers a tranquil escape in Key West neighborhoods. The park boasts stunning views of the harbor and the Atlantic Ocean, making it an ideal spot for picnicking, leisurely walks, or simply relaxing in the shade of swaying palm trees in Key West neighborhoods. The park also features various recreational amenities such as a playground for kids and fitness stations in Key West neighborhoods. The Truman Waterfront Park is a serene destination where you can unwind and enjoy the peaceful ambiance of Key West neighborhoods.
New Town History
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.
Things To Do in New Town
Smathers Beach, Key West’s largest public beach, is a haven for sun-worshipers and water sports enthusiasts. Its pristine white sands and crystal-clear turquoise waters create an idyllic setting for relaxation. The beach offers plentiful entertainment options, from Jet skiing, and paddleboarding to parasailing. Visitors can also enjoy beach volleyball, or simply unwind under palm trees with a picnic. Nearby vendors supply all the necessary gear for activities and refreshments. With its exquisite natural beauty and vibrant atmosphere, Smathers Beach is a must-visit spot in Key West.
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.
Garrison Bight Marina serves as a hub for boating and water-based activities in Key West neighborhoods. Located just north of Old Town and its neighborhoods, this marina offers a range of services, including boat rentals, fishing charters, and boat slips. Whether you’re an experienced boater or looking to try your hand at fishing in Key West neighborhoods, the marina is your gateway to exploring the crystal-clear waters surrounding the island. The convenient location and the friendly staff make Garrison Bight Marina a must-visit for all water enthusiasts 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.
The Fort East Martello Museum in Key West offers an immersive journey into the area’s history, from Civil War fortifications to local folklore. Visitors can explore the preserved fort, marveling at its 19th-century engineering and architecture. The museum also hosts a collection of local artists’ work, including the notorious Robert the Doll. The lush surroundings offer a serene backdrop, perfect for leisurely strolls. Its unique mix of history, culture, and nature makes the Fort East Martello Museum an essential stop on a Key West itinerary.
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.