Having spent countless weekends exploring Key West over the past few years, I’m often asked what makes this quirky island town so special. It’s a fair question, but one that’s surprisingly tough to answer – Key West is one of those places that feels different to everyone who visits.
“Key West has this way of making you forget about the mainland,” says Maria Rodriguez, a local tour guide who’s been showing visitors around for over two decades. “Some folks come for the history and Hemingway’s house, others for the sunset celebrations at Mallory Square, and plenty just want to kick back with a slice of key lime pie and watch the world go by.”
While you could easily spend weeks getting to know every corner of this southernmost slice of paradise, most visitors only have a few days to take it all in. So, I’ve put together a list of 21 places that’ll help you make the most of your time in Key West, whether you’re here for the history, the food, or just that laid-back island vibe.
Duval Street
Of all the streets I’ve walked in Key West, none captures the spirit of the island quite like Duval Street. This mile-long stretch runs from the Gulf of Mexico to the Atlantic Ocean, acting as the beating heart of Key West’s entertainment scene. It’s where tourists and locals alike wander between colorful old buildings housing quirky shops, open-air bars, and seafood restaurants that spill out onto the sidewalks. During the day, you’ll find people ducking into art galleries and boutiques, while at night the street transforms into a lively celebration with live music pouring out of every doorway. It’s not just a street – it’s Key West’s version of Bourbon Street, and walking its length gives you a real taste of what makes this island so special.
Mallory Square
Locals and tourists alike have been gathering at Mallory Square since the 1960s for its famous sunset celebration, a tradition that’s become synonymous with Key West culture. Located at the western edge of the historic waterfront, this lively plaza comes alive two hours before dusk as street performers, food vendors, and artists set up shop along the brick pathway. The square itself dates back to the 1800s when it served as the heart of Key West’s maritime commerce. Today, visitors can still spot fishing boats and cruise ships gliding past while enjoying fresh conch fritters or watching sword swallowers and jugglers perform their acts. The nightly sunset here is more than just a natural phenomenon – it’s a community celebration where everyone pauses to watch the sun melt into the Gulf of Mexico, often with live music playing in the background and the sound of applause marking the day’s end.
Fort Zachary Taylor Historic State Park
Fort Zachary Taylor State Park first caught my eye during a summer road trip to the Florida Keys in 2019. Located at the southern tip of Key West, this historic Civil War-era fort sits on 54 acres of pristine coastal land where the Gulf of Mexico meets the Atlantic Ocean. The park’s white sand beach wraps around crystal-clear waters that are perfect for snorkeling, while shaded picnic areas nestle beneath rustling Australian pines. The fort itself, built in the mid-1800s, offers fascinating guided tours through its brick corridors and gun rooms, telling tales of its role in both the Civil War and Spanish-American War. The observation deck provides unmatched views across the water, where cruise ships glide by and the sky melts into endless shades of blue and gold at sunset.
Ernest Hemingway Home and Museum
Literature fans flock to the Ernest Hemingway Home and Museum in Key West to explore the Spanish Colonial mansion where the famous author lived and wrote for over a decade. The property serves as both a time capsule of 1930s Florida Keys life and a sanctuary for around 60 six-toed cats, many descended from Hemingway’s own beloved pet Snow White. Visitors can wander through the rooms where “Papa” penned some of his most celebrated works, including “For Whom the Bell Tolls,” or stroll through the lush gardens surrounding the house. The museum offers guided tours throughout the day, providing fascinating insights into Hemingway’s colorful life in Key West, but many guests find themselves equally entertained by the resident felines who lounge freely throughout the property.
Southernmost Point Buoy
Stand at the edge of the continental United States at the Southernmost Point Buoy, one of Key West’s most photographed landmarks. This colorful concrete monument marks the southernmost spot in the continental U.S., sitting just 90 miles from Cuba. Stop by early in the morning to avoid the long lines of visitors waiting to snap their picture with this iconic marker. While you’re there, take a stroll through the charming neighborhood and grab a Cuban coffee from one of the nearby cafes to make your visit even more memorable.
Key West Butterfly and Nature Conservatory
If you’re searching for a little magic in Key West, the Butterfly and Nature Conservatory should be at the top of your list. This glass-enclosed wonderland houses hundreds of butterflies that float freely through the air, often landing right on visitors as they walk through the tropical garden setting. It’s like stepping into another world – the temperature stays at a perfect 85 degrees, and the winding paths take you past flowering plants, small waterfalls, and even a pair of pink flamingos named Rhett and Scarlett. While the sight of colorful butterflies might be the main draw, I’ve found the real joy comes from watching kids’ faces light up when a butterfly decides to perch on their shoulder.
Dry Tortugas National Park
Ever wondered what it’s like to snorkel around a Civil War-era fort? About 70 miles west of Key West lies Dry Tortugas National Park, where crystal-clear waters meet historic Fort Jefferson – a massive 19th-century fortress on a tiny coral island. This remote paradise is only accessible by boat or seaplane, making it one of Florida’s best-kept secrets. You can explore the fort’s brick walls and moat, spot sea turtles gliding through the shallow waters, or dive among colorful coral reefs teeming with tropical fish. The park’s seven small islands also offer excellent bird watching, with species like frigate birds and sooty terns calling these sandy shores home.
Smathers Beach
If you’re looking for the best beach experience in Key West, Smathers Beach is where you’ll want to be. This 2-mile stretch along the southern shore is the largest public beach on the island, offering plenty of room to spread out your towel and soak up the Florida sun. The calm, shallow waters make it perfect for families with kids, while active types can try their hand at volleyball, parasailing, or kayaking along the shore. It’s not the secluded paradise you might find in the Caribbean – the nearby road can get busy – but the rows of swaying palm trees and clear blue waters more than make up for it. Plus, the beach’s location just minutes from downtown means you can easily combine your beach day with other Key West adventures.
Sunset Pier
I always recommend watching the sunset at Sunset Pier to anyone visiting Key West. Located at the end of Duval Street at Ocean Key Resort, this lively waterfront spot combines everything that makes Key West special – live music, fresh seafood, and some of the best views of the sun dipping into the Gulf of Mexico. The open-air bar and restaurant lets you sip tropical drinks while pelicans dive for fish and sailboats glide by in the golden light.
Harry S. Truman Little White House
Ever wondered where U.S. presidents go to escape the pressures of Washington? The Harry S. Truman Little White House in Key West served as President Truman’s winter retreat during his time in office. This historic home, built in 1890 as naval officer housing, later became a sanctuary where Truman spent 175 days of his presidency working and relaxing in the Florida sunshine.
Key West Lighthouse and Keeper’s Quarters Museum
Step back in time at the Key West Lighthouse Museum, a maritime beacon that’s been watching over the island since 1848. Climb the 88 iron steps to reach the observation deck, where you’ll get a bird’s-eye view of the entire island and the endless blue waters beyond. Inside the keeper’s quarters, you can explore exhibits about the lighthouse keepers who once called this place home, including the story of Barbara Mabrity – one of Florida’s first female lighthouse keepers. It’s an ideal spot for history buffs and anyone looking to snap some great photos of Key West from above.
Audubon House & Tropical Gardens
If you want to step back in time to 19th-century Key West, head to the Audubon House. This elegant home showcases the work of famous naturalist John James Audubon, who visited the Florida Keys in 1832. Inside, you’ll find original Audubon prints, period furniture, and a peek into the lives of Key West’s wealthy maritime merchants. The surrounding tropical gardens feature the same plants that attracted the colorful birds Audubon painted.
Fort East Martello Museum
Fort East Martello Museum stands as a Civil War-era fortress on the southern edge of Key West. Like many historic sites in the Florida Keys, this brick stronghold tells tales of military history, but unlike others, it houses an unexpectedly peculiar collection of local artifacts and folk art. You’ll find everything from salvaged shipwreck pieces to the infamous Robert the Doll, a supposedly haunted toy that draws paranormal enthusiasts from across the country. Because of the fort’s rich connection to both Civil War history and Key West’s maritime past, it became a cultural center in 1950, and you’ll discover rooms filled with military memorabilia, local artwork, and curious objects that paint a picture of the island’s unique heritage.
Higgs Beach
Looking for a local beach that feels like old-school Key West? Higgs Beach offers exactly that laid-back island vibe, complete with swaying palm trees and historic charm. This peaceful stretch of sand is where you’ll find the only African refugee cemetery in the United States, dating back to 1860, alongside one of the island’s oldest wooden piers. The beach park comes with all the essentials – tennis courts, a playground for the kids, and even a dog park where four-legged friends can run free. When hunger strikes, grab a Cuban coffee and sandwich at the beachfront café, or set up your own picnic while watching sailboats drift by in the crystal-clear waters.
Key West Aquarium
Step back in time at the Key West Aquarium, one of Florida’s oldest aquariums built in the 1930s. You can get up close with local marine life in the touch tanks, where friendly stingrays glide past your fingers, or watch as sharks swim overhead in the Atlantic Shore exhibit. For a special treat, time your visit with one of the daily shark feedings, where you’ll learn about these misunderstood creatures from marine experts. Kids especially love the guided tours, where they can hold horseshoe crabs and learn about sea turtle rescue efforts that the aquarium supports.
Mel Fisher Maritime Museum
Step back in time at the Mel Fisher Maritime Museum, where real-life treasure hunting comes to life. This fascinating museum houses artifacts recovered from shipwrecks dating back to the 1600s, including an impressive $450 million worth of gold and silver found on the Nuestra Señora de Atocha. You can explore detailed exhibits about maritime history, see authentic pieces of eight, and learn about Fisher’s 16-year quest to find the sunken Spanish galleon. For an extra special experience, join one of the behind-the-scenes conservation tours where you can watch experts preserve newly discovered treasures.
Key West Cemetery
Many travelers come to Key West Cemetery seeking a unique glimpse into the island’s history, but this 19-acre site offers more than just a final resting place. Located in the heart of Old Town, the cemetery houses over 100,000 graves – nearly three times the current population of Key West. The unusual above-ground vaults and sometimes humorous epitaphs (like “I told you I was sick”) tell stories of the city’s past residents, from Cuban cigar makers to victims of the 1892 fever epidemic. While some might find it odd to visit a cemetery during vacation, this peaceful spot provides a fascinating look at Key West’s cultural heritage and serves as a quiet escape from the busy streets of downtown.
Interesting Fact:
Established in 1847 after a hurricane washed away the old cemetery, the Key West Cemetery is famous for its quirky headstones with humorous epitaphs like “I told you I was sick” and “At least I know where he’s sleeping tonight.” The 19-acre cemetery in the heart of Old Town holds around 100,000 people – more than three times the current population of Key West – and includes separate sections for Cuban revolution veterans, sailors who died in the explosion of the USS Maine, and victims of the 1878 yellow fever epidemic.
West Martello Tower
Looking for a peaceful escape in Key West? The West Martello Tower is where you’ll find it. This former Civil War-era fort has been transformed into a beautiful garden sanctuary run by the Key West Garden Club. What makes it special is how nature has taken over the old military structure – vines climb up brick walls while tropical plants fill every corner of the grounds. The garden offers a perfect mix of history and natural beauty, with shaded paths winding through orchids, native plants, and a charming butterfly garden.
The Key West Shipwreck Museum
Maritime history buffs flock to the Key West Shipwreck Museum to learn about the island’s fascinating shipwrecking industry, but visitors quickly discover it’s also an interactive journey through time. The museum occupies a replica of a 19th-century warehouse and tells the story of the “wreckers” who made their fortune salvaging cargo from ships that ran aground on nearby reefs. Through actor-led presentations, artifacts from actual shipwrecks, and a 65-foot lookout tower with views across the water, guests can experience what life was like during Key West’s maritime golden age. You can climb the tower, lift a silver bar recovered from the ocean floor, and watch films about the dangerous yet profitable world of shipwreck salvage that helped make Key West one of the richest cities in America during the 1800s.
Sloppy Joe’s Bar
Located at the corner of Duval and Greene Streets since 1937, Sloppy Joe’s Bar stands as one of Key West’s most legendary watering holes. Ernest Hemingway made this spot his second home during his time on the island, drinking and writing while surrounded by the salty characters who gave Key West its soul. The bar’s worn wooden floors and walls lined with decades of memorabilia tell stories of wild nights and colorful patrons who’ve passed through its doors. Live music fills the air every day from noon until late, while bartenders serve up their famous Sloppy Joe sandwiches and rum runners to a mix of locals and tourists. The annual Hemingway Look-Alike Contest, held here each July, draws hundreds of white-bearded men hoping to be crowned Papa’s closest doppelganger, turning the already lively bar into an unforgettable spectacle of Key West culture.