Key West isn’t just a destination—it’s an experience. Stepping off the cruise ship puts you in a colorful world of swaying palms, Victorian architecture, and sunlit streets with a quirky buzz you’ll not find in other ports. And the good news? Key West’s breathtaking scenery is packed into just over a mile of walkable magic.
A self-guided walking tour of Key West gives you a chance to visit iconic landmarks like Ernest Hemingway’s old haunts, Southernmost Point, and shipwreck museums. Also, the vibrancy of Mallory Square and Duval Street is something hard to find in other ports. As you wander past pastel homes, you feel the tropical warmth on your skin. End your day with a slice of classic Key lime pie and a frozen margarita for the perfect Key West experience.
So lace up your walking shoes, grab your sunscreen, and let’s hit the streets. This isn’t just a tour—it’s your gateway to uncovering the hidden gems of one of the most captivating stops on your cruise.
Self-Guided Walking Tour of Key West for a Cruise Day
Strolling the streets of Key West is an unforgettable taste of the Caribbean without leaving the United States. The most popular cruise lines like Carnival, Holland America, Celebrity, and the smaller Royal Caribbean ships include the port in many cruise sailings to the Caribbean or Mexico.
Many cruisers rate it as one of the best stops on a Caribbean cruise. One commented that the vibe, seafood, and quirky historical places like Hemingway’s six-toed cats in the “Conch Republic” are well worth seeing. Another traveler shared, “Key West is a blast with so much history and things to enjoy on a cruise day.”
Arriving at Key West Cruise Port
Most cruise ships dock at Mallory Square or the Truman Annex on the island’s western side. Other ships may dock at Navy Mole (Outer Mole Pier) on the town’s outskirts. It’s only a few steps from disembarking the ship to start exploring the sites and attractions of this beautiful island city.
Stop 1: Mallory Square
Mallory Square at the cruise ship docks is the lively starting point where the walking tour begins. You’ll find musicians, jugglers, conch-fritter vendors, artisans, and various entertainers filling the square. Many cruise passengers say that the vibe sets the scene for exploring Key West.
Must-see attractions in Mallory Square include Wreckers’ Monument—a celebration of the city’s fascinating salvaging history and Sponge Market. Here, you get a fascinating glimpse into maritime history as it comes alive amid displays of salvaged sponges and unique trinkets. One visitor loved “the chance to pick up something authentic, not the usual tacky port souvenirs.”
Depending on your cruise departure time, you may get the chance to snap a photo of the Gulf of Mexico at sunset. Another popular photo opportunity is standing beside the “Welcome to Mallory Square” sign, showcasing many of the attractions on the walking tour. One cruiser said that it’s a great memento and a must-have photo to kick off the island adventure.
Time needed: 20-30 minutes
Stop 2: Key West Shipwreck Museum
A short stroll from the cruise ship docks is the Key West Shipwreck Museum located at 1 Whitehead Street. Here, you step back to the 19th century to view displays of wreck salvage in the Florida Keys. It’s also fascinating to see artifacts from the Isaac Allerton shipwreck, genuine silver bars from Spanish galleons, and to read about people who made their fortunes from wreck salvage.
Want some of the best photos of Key West? Climb the 65-foot observation tower at the museum. You can enjoy panoramic views of the island and ship docks. Visitor comments on forums described it as “a fascinating dive into a lesser-known slice of history” and “surprisingly fun for adults and kids alike.”
Whether you’re a history buff or simply curious, the Shipwreck Museum is a memorable stop you’ll be talking about long after your cruise ends.
Time needed: 30-40 minutes
More Stops to Explore if You Have Time
The Key West Aquarium is a great place to bring kids and get up close to marine life. The small but fascinating place has a touch tank with sea stars, conch, sea cucumbers, hermit crabs, horseshoe crabs, and slate pencil sea urchins. It’s a hit with kids and adults alike.
When heading to the next stop, Duval Street, you can stop off at the Mel Fisher Maritime Museum. This attraction gives you a chance to learn about the real Pirates of the Caribbean. Visitors say the exhibitions of gold coins, sunken treasure, and the slave trade are worth seeing.
Opposite the Maritime Museum is Audubon House & Tropical Gardens. Here, you can Explore the stunning 19th-century home of Captain John Geiger, surrounded by lush gardens filled with orchids and native plants. One visitor called it “a quiet gem in the heart of Key West, perfect for history lovers and garden enthusiasts.”
Stop 3: Duval Street
From the corner of Whitehead Street and Greene Street, walk 2 minutes north to Duval Street—the vibrant heart of Key West. Stretching from the Gulf of Mexico to the Atlantic Ocean, this 1.3-mile street is packed with a lively mix of quirky shops, art galleries, historic bars, and local eateries. One cruiser described it as “the kind of place where you can stroll, sip, and soak in the unique vibe of Key West.”
What are the must-see spots on Duval Street? Here are a few suggestions based on my trips to Key West and what I read on various forums:
- Sloppy Joe’s Bar: A historic watering hole famously frequented by Ernest Hemingway, described as “a must-stop for drinks and a great vibe.”
- Smallest Bar in Key West: Tucked away and easy to miss, but cruisers love its quirky charm and tropical cocktails, calling it “a fun photo op and a unique Key West experience.”
- DJ’s Clam Shack: Known for its incredible lobster rolls and conch fritters, one visitor said, “The food here is unforgettable—easily the best bite I had in Key West.”
- Guild Hall Gallery: Online reviews recommend this hidden gem, calling it a fantastic spot to find reasonably priced, locally made art. You can browse through stunning oil paintings, delicate watercolors, and striking photographs—there’s something for every taste and budget.
- Key West Pottery: Art lovers say this spot is a must, featuring handcrafted ceramics inspired by Key West’s natural beauty and colorful vibe. One traveler praised its “eye-catching designs, quality craftsmanship, and vibrant patterns” that appeal at every price point.
Time needed: 40-60 minutes
Stop 4: Key West Cemetery
As you meander along Duval Street, turn left onto Olivia Street just before Ernest Hemingway Home until you come to Key West Cemetery. While it sounds like a morbid stop, the cemetery provides a unique and quirky look into the island’s past. You’ll walk among colorful epitaphs, historic monuments, and a tranquil atmosphere.
Notable features of the cemetery include:
- Humorous headstones and epitaphs like:
- “I told you I was sick.”
- “If you’re reading this, you desperately need a hobby.”
- “I’m just resting my eyes.”
- Burial place of Abe Sawyer—a man 40” tall but buried in a full-sized grave
- USS Maine Memorial honoring sailors killed in the Spanish-American war
After exiting the cemetery, go back along Olivia Street to Hemingway’s House.
Time needed: 30-40 minutes
Stop 5: Ernest Hemingway Home and Museum
Ernest Hemingway’s home is one of the most popular attractions in Key West. It’s the place where the writer penned some of his most famous works like To Have and Have Not, Green Hills of Africa, and Death in the Afternoon. The museum is packed with memorabilia of Hemingway’s life and work.
Visitors highly rate Ernest Hemingway Home and Museum for its charm and authenticity. Highlights of the tour are Hemingway’s writing studio and the famous six-toed cats. One review noted, “The lush gardens, fascinating stories, and unique vibe make this one of Key West’s best attractions.”
One cruiser wrote, “It’s a must-see for history and literature lovers.” Another said that the garden, house, and swimming pool are all magnificent, with many praising the knowledgeable tour guides. However, it’s good to note that the place is always packed with crowded group tours.
Here’s a funny story I heard. The iconic pool at Hemingway’s home—the first in Key West—came with a jaw-dropping $20,000 price tag in the 1930s. Frustrated, Hemingway famously threw a penny into the wet cement, declaring to his second wife, “You’ve spent all but my last penny, so you might as well have that!” You can still see the penny today—a cheeky reminder of their legendary squabbles.
A favorite part of the Ernest Hemingway Home and Museum tour is the six-toed cats. These are descended from Hemingway’s polydactyl cat, Snow White. The friendly felines roam the property freely. Guests describe them as “adorable, photogenic, and surprisingly social.”
Fun Fact: The Blue Heaven in Bahama Village (Petronia Street) was the original site of Hemingway’s boxing ring.
Time needed: 1 hour
Stop 6: Key West Lighthouse and Keeper’s Quarters Museum
Across the street from the Hemingway home is the Key West Lighthouse and Keeper’s Quarters Museum. Built in 1848, it was one of the first in the U.S. to have a female keeper, the resilient Barbara Mabrity. Here, you can climb the 88 steps to enjoy spectacular views from the top.
The Keeper’s Quarters has artifacts and displays showcasing the life of lighthouse keepers. Visitors also learn about the Fresnel Lens and the powerful beams it could create to keep mariners safe at night.
Fun fact: It’s said that Barbara’s ghost continues to haunt the lighthouse.
Time needed: 20-30 minutes
Stop 7: Southernmost Point Buoy
The Southernmost Point Buoy is one of Key West’s most iconic landmarks, marking one of the farthest southern points in the continental United States, just 90 miles from Cuba. This massive, colorful concrete buoy has become a must-visit photo stop for travelers from around the world.
If you want to take a break from walking, head along South Street to the Southernmost Beach Cafe. This is a great place to cool off with a drink or snack and enjoy superb ocean views.
Fun fact: Whitehead Spit is technically the southernmost point in the U.S.; however, it’s not accessible to the public.
Time needed: 10 minutes
Stop 8: Fort Zachary Taylor Historic State Park
The southwestern tip of Key West is Fort Zachary Taylor Historic State Park. The 54-acre park provides a fascinating glimpse into the critical roles it played in the Civil War and Spanish-American War. You can have fun exploring the vaulted rooms and walking past cannons and gun ports.
The beach at Fort Zachary is one of the best beaches in Key West. It has shaded cabanas, calm waters, and plenty of opportunities for snorkeling and fishing. If you’re interested in relaxing, there are beach cafes serving snacks and refreshments.
Time needed: 20–30 minutes
Stop 9: The Green Parrot Bar
From Fort Zachary, walk along Butler Blvd and then Southard Street to the Green Parrot Bar. The bar is a hit with locals and tourists alike, who enjoy cocktails, great food, and live music. Its claim to fame? It’s the oldest bar in Key West and the first on Route 1.
From the Green Parrot, it’s a short walk to the Truman Little White House, the perfect way to round off your day in Key West.
As you head back in the direction of the cruise port, don’t forget to stop at the corner of Whitehead Street and Fleming Street. Here, you can take snaps of one of the most photographed spots in the city—the US1 Mile Marker 0 sign.
Time needed: 30 minutes
Stop 10: Truman Little White House
The Truman Little White House is a historic gem near the cruise port and the last stop on the walking tour. Built in 1890 as a naval station command headquarters, it later became President Harry S. Truman’s winter retreat during his presidency. Known as the “Winter White House,” it hosted important political meetings and remains a key piece of American history.
What to see at the Little White House:
- Truman-era memorabilia, from his desk to personal photographs and other artifacts
- Tour meeting rooms, including where critical decisions were made during the Cold War
- Well-kept gardens where you can relax before returning to the cruise ship.
The Truman Little White House offers a rare insight into the private life of one of America’s most influential presidents.
Photo ops: Snap a picture of the stately white exterior or Truman’s poker table, which presents a fun glimpse into his more casual side.
Time Needed: 30–45 minutes
Must-Try Dishes to Eat in Key West
Key West is a food lover’s dream, where fresh seafood meets bold Caribbean and Floridian flavors. Visitors rave about the island’s legendary Key lime pie—“the best I’ve ever had”—at Kermit’s Key Lime Pie Shoppe. DJ’s Clam Shack is a must for buttery lobster rolls and crispy conch fritters, while Blue Heaven’s Key lime pancakes and Schooner Wharf Bar’s dockside vibes add even more unforgettable bites to your day.
When exploring Key West, sampling local dishes is an essential part of the experience. From the fresh catch of the day to quirky island specialties, there’s no shortage of culinary delights to enjoy.
Which dishes in Key West perfectly capture the flavors of this tropical destination? Here are six of my favorites:
- Key lime pie: Nothing gets more authentic than the island’s signature dessert. Made with lime juice, condensed milk, and a crusty base, all topped with soft meringue.
- Spiny lobster: Common in most restaurants, the spiny lobsters are sautéed, fried, or broiled and coated in tasty key lime butter.
- Conch fritters: A true island classic, crispy and full of flavor. You may find them in the signature Key West Chowder.
- Stone crab claws: Harvested at Key West, the sweet crab meat is best enjoyed with a tangy mustard sauce.
- Mahi-Mahi tacos: Fresh and zesty fish-filled Mahi-Mahi tacos or sandwiches are a local favorite. Where’s the best place to try them? Eaton Street Seafood Market.
- Hogfish: This reef fish has a delicious taste and light texture. Locals enjoy the fish fried or grilled along with key lime tartar sauce.
Enjoy Your Cruise Day in Key West
Key West’s tropical climate means warm temperatures and plenty of sun year-round, so dressing for comfort and weather is critical. Its compact size and walkable layout mean it’s easy to spend a cruise day on the island. However, it’s vital to plan well as just the walking can take 1.5 to 2 hours, and combined with stops—6 to 8 hours. Therefore, you may need to adjust the time you spend at each location.
Start early to beat the crowds and heat. As with any walking tour in the tropics, wearing comfortable shoes and staying hydrated is vital. Don’t rush. It’s best to enjoy Key West strolling the colorful streets at a leisurely pace.
Here are a few ideas on what to pack in your day bag:
- Sunscreen: A reef-safe option is ideal for both you and the environment.
- Reusable water bottle: Staying hydrated is essential in the heat.
- Small backpack or crossbody bag: To carry essentials like your phone, wallet, and any purchases.
- Portable phone charger: Capture every moment without worrying about battery life.
Make the Most of Your Key West Adventure
Key West is a favorite stop on Caribbean cruise ship itineraries, and I’ve read about many cruisers who only choose cruises that include the island. Its walkability means you can see most of its iconic landmarks and savor local Key West flavors without booking an excursion. Wishing you a fun-filled, sun-soaked day in this tropical paradise as you start or end your cruise vacation.
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