Key West, Florida is a vibrant and exciting destination, offering something for every traveler, whether you’re drawn to its rich history, stunning natural beauty, or lively atmosphere. While the island is known for its popular attractions, there are many hidden gems that most tourists miss. In this guide, we’ll highlight the must-see fun and historical attractions and a few off-the-beaten-path destinations that make Key West truly unforgettable.
Choosing the Best of Key West: Where to Start
When planning your trip to Key West, the sheer number of attractions can be overwhelming. Do you focus on the area’s fascinating history and culture? Do you indulge in its buzzing nightlife? Or do you want to get out on the water and enjoy snorkeling or diving? The options are endless, and balancing the popular and lesser-known spots can be challenging.
Ultimately, the key to a memorable Key West experience lies in exploring the iconic attractions and hidden treasures that aren’t on the usual tourist radar. By mixing well-known destinations with those less traveled, you will create a truly one-of-a-kind vacation.
Sunset Celebration at Mallory Square: A Must-See Event
One experience you absolutely cannot miss in Key West is the iconic Sunset Celebration at Mallory Square. As the sun sets over the water, the sky fills with vibrant hues of pink and orange and everyone is in awe. This nightly event is filled with music, street performers, and local artists, all contributing to the electric atmosphere. Locals and tourists gather together to witness the breathtaking view, creating a sense of community that captures the heart of Key West.
The Mallory Square celebration is more than just a beautiful sunset; it’s an immersive experience, offering entertainment, local culture, and a glimpse into the laid-back yet lively spirit of the island. It’s the perfect way to wind down after a day of exploration.
Discovering Hidden Tranquility: Duval Street Pocket Park
While Mallory Square and the famous landmarks in Old Town can be bustling with visitors, there’s also a quieter, more serene side to Key West. One such spot is the Duval Street Pocket Park, a hidden gem tucked away from the typical tourist route. This peaceful park features lush landscaping, tranquil seating areas, and a relaxing atmosphere—perfect for unwinding after a busy day of sightseeing.
For those who like a bit of adventure, head out to the end of the park’s dock at sunrise. It’s a great spot to watch the daybreak, offering an incredible view of the island in the early morning light. If you’re lucky, you might catch this magical moment just as we did, turning an ordinary morning into an extraordinary experience.
Iconic Landmarks: Southernmost Point and Hemingway’s Home
Southernmost Point Buoy
Key West is home to several iconic landmarks, starting with the Southernmost Point Buoy. Marking the southernmost point in the continental U.S., this landmark is a must-see for anyone visiting the island. The buoy is located near the popular Southernmost Point attraction, where you’ll find a long line of people eager to snap a photo. To avoid the crowds, try getting there early in the morning. Link this up with your trip to the Duval Street Pocket Park, nearby, to catch the sunrise.
Overseas Highway – Mile Marker 0
The Overseas Highway, with its mile marker 0 located in Key West, Florida, is a historic and iconic roadway that stretches over 100 miles through the Florida Keys. Originally built as a railroad in the early 20th century, it was later converted into a highway due to damage caused by a hurricane. The highway offers stunning views of the crystal-clear waters of the Gulf of Mexico and the Atlantic Ocean, making it a popular route for tourists seeking a scenic drive. Mile marker 0 serves as a landmark for travelers looking to explore Key West’s vibrant culture and attractions, including its bustling nightlife, world-renowned sunsets at Mallory Square, and historical sites like the Ernest Hemingway Home and Museum. Another perfect location for a picture.
Cuban Queen Coffee
Cuban Queen Coffee in Key West is a hidden gem for coffee lovers looking for a unique and authentic experience. This cozy little spot offers a selection of Cuban-style coffee drinks that are rich, bold, and full of flavor. As soon as you walk in, you are greeted by the warm aroma of freshly brewed coffee and the friendly faces of the staff. The decor is charming with its vibrant colors and Cuban-inspired artwork adorning the walls. With its relaxed atmosphere and unbeatable coffee, Cuban Queen Coffee is a must-visit spot for anyone craving a taste of Cuba right in the heart of Key West and to get a perfect selfie as well..
Ernest Hemingway’s Home and Museum
Another essential stop for history lovers is Ernest Hemingway’s Home and Museum. The property, which dates back to the early 1850s, was once the residence of the famed author. It is beautifully preserved, with many of Hemingway’s personal items still on display, offering an intimate look at the writer’s life. One of the most interesting features of the house is the infamous “six-toed cats,” descendants of Hemingway’s original pets, who still roam the grounds.
The Conch Republic Mural
Did you know that Key West, Florida once pretended to break away from the United States? It was called the Conch Republic and it happened in 1982. The people of Key West were upset about a border patrol blockade that was causing problems on the island. So, they declared themselves independent and even threw stale Cuban bread at the U.S. to show they meant business. But don’t worry, it was all in good fun! The name “Conch Republic” comes from the nickname for Key West residents and all the conch shells you can find there.
Food, Fun Nightlife, and People Watching on Duval Street and Around
Duval Street in Key West is a historic and vibrant hub of activity, offering visitors a variety of attractions and experiences. Lined with quaint shops, colorful boutiques, lively bars, and delicious restaurants, this bustling thoroughfare captures the essence of the island’s laid-back yet energetic atmosphere.
Duval Street provides an insight into Key West’s rich culture and history. Visitors can wander along the palm-lined street, sampling fresh seafood, sipping cocktails at world-famous bars like Sloppy Joe’s, or taking in live music performances on bustling patios. Whether you’re looking for a taste of authentic Key West charm or simply wish to soak up the tropical ambiance, Duval Street promises an unforgettable experience for all who visit.
It’s hard to tell from the picture but the girl in the black dress is trying to throw a quarter up into the fish’s mouth. I don’t know what they can win but it was entertaining to watch them try.
Key West’s Fascinating History and Unique Attractions
President Harry S. Truman’s Little White House
Beyond its lively culture and beautiful beaches, Key West is steeped in fascinating history. One of the most significant historical sites is the Harry S. Truman Little White House. This residence served as the Winter White House for President Truman during his presidency and is now a museum honoring his legacy. From this location, Truman made crucial decisions, including the Marshall Plan and the formation of NATO.
Key West Lighthouse
For those interested in maritime history, a visit to the Key West Lighthouse is a must. Built in 1825 and standing at 86 feet tall, the lighthouse provides sweeping views of the island and its surrounding waters. Visitors can climb to the top and learn about the lighthouse’s vital role in guiding ships through the treacherous waters around Key West. The attached museum offers a deeper look into the island’s seafaring past and the lighthouse’s role in ensuring safe passage for sailors.
Dry Tortugas National Park
The Dry Tortugas National Park excursion is a unique and remote experience that offers visitors the chance to explore a remote historical and beautiful location. Located about 70 miles west of Key West, Florida, this national park is only accessible by boat or seaplane, making it a secluded and peaceful destination for nature enthusiasts.
The park is home to Fort Jefferson, a historic military fortress surrounded by crystal clear waters and vibrant coral reefs. With opportunities for snorkeling, birdwatching, and beachcombing, visitors can immerse themselves in the natural beauty of the area. The excursion also provides educational opportunities with ranger-led tours and exhibits about the park’s history and ecology. Overall, the Dry Tortugas National Park excursion offers a memorable and enriching experience for those seeking adventure and exploration in a stunning natural setting.
Ghost Tours: Explore Key West’s Paranormal Side
Key West Ghost Tour
Key West is not only rich in history but also in mystery. The island has a long history of paranormal activity, with numerous haunted buildings and ghostly tales that date back centuries. Ghost tours are a popular way to explore this spooky side of Key West, and for those willing to venture into the night, they provide a fascinating glimpse into the island’s eerie past.
Haunted Locations
One of the more famous haunted spots on the tour is Robert the Doll, a cursed object that terrorized its young owner. Visitors also explore St. Paul’s Episcopal Church, where ghostly children are said to play near a statue of an angel, and the Marrero Mansion, known for its chilling stories. The tour includes stops at several iconic locations like Hemingway’s House, the Oldest House Museum, and the African Cemetery at Higgs Beach, each with its own eerie history and tales of the supernatural.
For anyone intrigued by Key West’s ghostly legends, this tour is a must-do. Whether you’re a skeptic or a believer, the stories and sites you’ll encounter are sure to leave a lasting impression.
Key West Cemetery: A Reflection of the Island’s Rich History
The Key West Cemetery, established in 1847, offers another look into the island’s rich cultural and historical legacy. Known for its unique above-ground tombs, the cemetery is the final resting place of notable figures, including author Tennessee Williams and former mayor Sloppy Joe Russell. The cemetery’s colorful memorials and quirky epitaphs make it a popular tourist attraction, offering a glimpse into Key West’s diverse history.
African Cemetery at Higgs Beach
The African Cemetery at Higgs Beach is a sacred and most poignant memorial to 294 African men, women, and children who perished in Key West in 1860. These individuals was being brought to the U.S. illegally as slaves, only to be rescued by the U.S. Navy. Though many died shortly after their arrival, the survivors were later relocated to Liberia, where they helped establish a new country for freed slaves. A beautiful monument stands in their honor, offering a powerful reminder of Key West’s history and its role in the abolition of the slave trade.
Exploring Key West’s Historic Churches and Iconic Homes
Key West is a place where history and culture seamlessly blend into the present, and one of the best examples of this is the Basilica of St. Mary Star of the Sea. Located in the heart of the island, this historic church offers more than just a religious experience—it’s a remarkable piece of architecture with a rich history dating back to 1905. As one of the oldest Catholic churches in Florida, the Basilica stands as a testament to the island’s vibrant past and its enduring role in the community.
The Basilica of St. Mary Star of the Sea
The Basilica’s stunning features, including its intricate stained glass windows and detailed marble altars, are captivating to visitors. These features not only add to the church’s beauty but also showcase the craftsmanship of a bygone era. For those interested in both religious history and architectural beauty, the church is a must-see destination. Visitors are welcome to attend Mass or simply enjoy the peaceful surroundings of the grounds.
The church’s bell tower, which rises above the surrounding buildings, provides a perfect opportunity for reflection or for admiring the architecture from a distance. Whether you’re religious or just appreciate cultural landmarks, a visit to the Basilica of St. Mary Star of the Sea is an essential part of experiencing the charm and history of Key West.
A Stroll Through Key West’s Historic Homes
Key West’s history is also vividly displayed through its historic homes, many of which reflect the island’s 19th-century charm. As the video highlights, there are many beautiful historical homes and buildings scattered across the island, each with its own story to tell.
The Oldest House Museum
The Oldest House Museum in Key West is a historical gem that offers visitors a glimpse into the island’s past. Built in 1829 by Captain Francis Watlington, this charming house is an excellent example of architecture from the early 19th century. The museum showcases the life of Key West’s early inhabitants through exhibits featuring period furnishings, artifacts, and photographs. The Oldest House Museum is a must-visit destination for those looking to deepen their understanding of Key West’s fascinating past.
Tennessee Williams Museum
Tennessee Williams’ connection to Key West, Florida is deeply ingrained in both the literary and cultural history of the island. Williams first visited Key West in the 1940s and eventually made it his full-time home in 1949, finding solace and inspiration in its serene beauty and vibrant artistic community. Williams’ impact on Key West can still be felt today through sites like the Tennessee Williams Exhibit at the Key West Museum of Art & History, which showcases memorabilia from his time spent on the island. His legacy continues to draw visitors and artists alike to Key West, cementing its place as a haven for creative expression and honoring one of America’s most revered playwrights.
The Oldest Schoolhouse
The oldest schoolhouse in Key West was constructed in 1847 and operated as a learning institution until 1972. The “Conch School”, located on Whitehead Street, stands as a testament to the educational history of Key West. The architecture of the building reflects the traditional one-room schoolhouse design, with intricate woodwork and a prominent bell tower. The schoolhouse has been meticulously preserved over the years, with original furnishings and artifacts displayed throughout to provide visitors with a glimpse into what schooling was like in the mid-19th century.
The Famous Kapok Tree
The Kapok Tree in Key West, is a majestic specimen located on the grounds of the Monroe County Courthouse. It holds great significance both botanically and culturally. This towering tree, native to Central and South America, is a symbol of tropical abundance and resilience in the heart of Key West.
Great Food
Old Town Mexican Cafe
While walking down Duval Street, we made a stop by the Old Town Mexican Cafe. It is their take on Southwest and authentic Mexican cuisine. The Cafe started their restaurant in 1999 and is still going strong. We highly recommend this cafe as the food was delicious.
Duffy’s Steak and Lobster House
We took the all-day excursion out to Dry Tortugas National Park. We asked the Excursion Manager what was his favorite place to eat. His reply was “Duffy’s Steak and Lobster House”. We took his advice and I sure am glad we stopped at Duffy’s for some great food.
The building that currently houses Duffy’s can be traced back to 1892 when the original Simonton Street – Truman Avenue corner structure was used as a “tinwares and stove store”. It went through a few more owners until 1948 when the original Duffy’s opened its doors. It changed hands a few times again with different restaurants until its current owners bought the building in 1987. In the summer of 1991, Duffy’s Steak and Lobster House opened its doors.
Conclusion
Key West is a city rich with history, from its iconic church to its storied homes and cultural landmarks. Whether you’re taking in the breathtaking architecture of the Basilica of St. Mary Star of the Sea, exploring the Oldest House Museum, or admiring the old-world charm of homes dating back to the 1800s, there’s no shortage of historical treasures to discover. For those planning to visit, Key West offers an unforgettable journey through time, where the past and present come together in perfect harmony.
If you like discovering Key West, you will want to check out all the other Florida Keys and Key West attractions including the Key West Ghost Tour, Dry Tortugas National Park, Pigeon Key and the Old 7-Mile Bridge, Feeding Tarpon at Robbie’s in Islamorada, and Shark Valley in the Everglades.
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Thank you for joining us on this tour of Key West’s attractions.. If you enjoyed this journey, be sure to check out our other posts featuring the Steamboat Natchez cruise, the Texas Hill Country, Key West and the Florida Keys, Arizona, Las Vegas and Nevada, and many more destinations. Don’t forget to subscribe to our channel for more cultural explorations and travel adventures.
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