Just 159 miles from Miami, you’ll find Florida’s southernmost city in Key West and my latest day trip to the tropical island city.
I typically recommend at least a two-night stay for a Key West trip, especially for first-time visitors. However, with my brother-in-law in town wanting to check out two Key West rum distilleries and only a few days to spare, a day trip only seem fitting.
I by no means am a big rum connoisseur, but any excuse for a Florida Keys road trip. So just like that, I was game for the impromptu day trip to Key West.
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Drive from Miami to Key West
The four-hour drive from mainland Miami to Key West takes you over the Overseas Highway past a chain of 40-plus islands, quaint fishing villages, seafood shacks, tiki bars, exotic coral reef parks, crossing over 42 bridges including the famous Seven Mile Bridge.
Heading from Miami to Key West? Book your Miami to Key West full day trip here!
See how many adventures you can check off this classic Florida Keys road trip bucket list.
Once you’re in the tiny island city of Key West, you’ll be treated to upscale marinas, pastel-colored conch-style houses, historical buildings, a quaint downtown strip, as well as plenty of boardwalks, white sandy beaches, and many sun drench tourists eager to check Hemingway’s favorite watering hole off their bucket list.
Whether you want to fuel up with some delicious local seafood, sample key lime pie, spend a day shopping, or lounging on the beach while watching the cruise ships sail past, there’s something to match all vibes in Key West.
Don’t forgot to pack these essentials for your Key West day trip:
Key West Day Trip Itinerary Map
Things to Do in Key West in a Day
1. Strolling Duval Street, Key West
You’ll undoubtedly spend a good part of your time in Key West strolling Duval Street, which stretches one mile north and south from the Gulf of Mexico to the Atlantic Ocean.
It’s a busy storefront and pedestrian stretch where you’ll find both tourists and locals, and everything from quirky shops, to art galleries and sidewalk cafes, to famous restaurants, bars, and beautiful Victorian homes with stately porches. It’s easily walkable, but you’ll find plenty of bike tours and rentals too.
Make the most of your time in Key West. Arrange your day trip tours and activities in advance here!
2. Papa’s Pilar Rum Distillery, Hemingway Rum Tour
We started our afternoon participating in the very edifying and enlightening Papa Pilar’s distillery tour. Our knowledgeable and charismatic tour guide Kirk made the experience even more meaningful. His knowledge of rum and the industry was impressive as he took us from pirates and smugglers to prohibition through modern-day.
Kirk guided us through the distillery, then provided a comprehensive history of Papa Pilar, rum culture, their rum distilling process, including personal notes and images from Hemingway’s life, and a generous tasting of the Papa Pilar dark and blonde rum varieties – which are phenomenal.
I found the dark Papa’s Pilar rum to be a little traditional with a hint of bourbon, while the lighter rum, blonde, was smooth and flavorful with hints of cinnamon.
The Papa’s Pilar Rum Distillery guided tours are $10 per person taking place at the top of the hour with the first one beginning at 11 am. This tour was worth the drive alone. Don’t miss this little gem on your next Key West trip.
Address: 201 Simonton St, Key West, FL 33040
3. Lunch at Sloppy Joe’s on Duval Street
Given it was lunchtime, stopping by the legendary Sloppy Joe’s for a quick bite only seem appropriate. Once a rowdy saloon popular with characters like Ernest Hemingway and other freethinkers, Sloppy Joe’s is a popular stop.
In the tap-room, you’ll find a variety of cold-crafted beers, and while its food menu offers loads of local pub fare, like soft pretzels, conch fritters, and peel & eat Key West shrimp. We ordered the fritters, Havana nachos, a sampler along with a few sloppy ritas and rum runners while a live cover band played nearby.
The food here is nothing to rave about, but in all likelihood, you’re stopping here for its iconic Key West status, music and cocktails rather than the food options.
The venue also features live music line up nearly every night, but the large crowds can make it almost impossible to snag a spot or table. It’s a little more manageable during the day, but also popular with the daytime cruise crowds.
Address: 201 Duval St. Key West, FL 33040
Join a local expert and uncover Key West’s hidden food gems.
4. Key West First Legal Rum Distillery Tour
Following lunch, we took part in the Key West First Legal Rum Distillery tour. The building has been operating as a distillery since 1900 and maintained many of its original, historical features.
It’s a short, but informative tour on the history of the distillery and distilling process, the locally prepared flavored rums, and a sip of 140 proof rum which the guide claimed was from the still.
A free rum sample is included in the tour, but a full tasting is available with the purchase of the $10 souvenir shot glass.
Tours are free and take place three times a day from Monday to Friday (at 1, 3 and 4 pm) and twice on Saturdays (1 and 3 pm). Keep an eye out for the cool salt-cured barrels in the distilling room.
Address: 105 Simonton Street, Key West, FL
5. Iconic Ernest Hemingway House
If you need a little break from the heat, I suggest moving on to the Iconic Ernest Hemingway House, where the famed author called home for almost a decade and wrote much of his life works.
Quietly nestled into Old Town, the National Historic Landmark home is a gorgeous display of classic Southern architecture, surrounded by lush gardens and gently swaying palms. Steeped in history and memorabilia about Hemingway’s life and work, it’s indeed a step back in time.
If you’re a cat lover, you’re in for a special treat, as you’ll undoubtedly stumble upon the 40-plus famous Hemingway polydactyl (six-toed) cats throughout the property.
The museum is open 365 days a year from 9 am to 5 pm., and a 30 minute guided tour is also included in the admission price. They accept cash only.
Address: 907 Whitehead Street, Key West FL, 33040
6. Historic Truman House Little White House
While you’re in historical touring mode, move on to the quaint white cottage known as the Truman House Little White House, which served as the former president’s winter residence and later a retreat for other U.S. Presidents seeking respite from Washington, amid threats of the Cold War.
The house is now a museum, fully restored with original furnishings used during Truman’s presidency, including the wallpapers, carpets, and upholstery.
You’ll find information on Truman and objects providing a glimpse into his personality including his tropical sports shirt dubbed the “Key West uniform,” a poker table and the famous “The Buck Stops Here” sign. A real gem for history buffs!
Photography is not permitted inside the house as it’s an active government building still used for official functions. The house and grounds are open 365 days a year and tours are offered from 9 am to 4:30 pm. Buy your tickets online here!
Address: 111 Front Street, Key West, FL
7. Mile Marker Zero
No trip to Key West is complete without a visit to Mile Marker 0, the longest north-south road in America, running 2,369 miles (3,813 km) up the East Coast, from northern Maine to Key West, marking the very end of interstate US 1.
The iconic sign is merely a street marker, but a fantastic photo opportunity, often surrounded by tourists, eager to attest that they’ve reached the end of the road. Look out for it near the courthouse, a quick one-block detour off Duval Street.
Address: Corner of Fleming Street and Whitehead Street, Key West, FL
8. The Southernmost Point
Our next stop found us at the iconic concrete buoy marking the continental United States’ southernmost point. Lined with visitors waiting in the Florida heat for a turn to capture their moment with the structure.
The marker is also a well-known pointer of Cuba’s proximity (about 90 miles) to Key West. Fun Fact: From this buoy, Key West is closer to Cuba than it is to Miami, which is roughly 160 miles north.
Although the site remains a popular tourist attraction, coordinates place the island’s actual southernmost point on Navy property located on the same land as the Truman House, but inaccessible to civilians.
While Florida’s actual southernmost point is on a private island, 10 miles southwest of Key West, making the buoyed marker the symbolic southernmost point.
Pro Tip: Plan your visit in the early morning, to avoid the crowds, long lines, and unbearable heat. Join a local expert and uncover Key West’s History and Culture on the Southernmost Walking Tour.
Address: Whitehead Street and South Street, Key West, FL 330403
9. Speakeasy Inn and Rum Bar
Time for a break? Walk along Duval Street, a short distance from the southernmost point buoyed, you’ll find the Speakeasy Inn, a historic building with beautiful architectural features that have been lovingly restored.
Just steps from the beach, it’s a small laid-back atmosphere, with an excellent stock top-shelf rum selection, that’ll easily impress any run aficionado. It at least passed the test with my rum enthusiast companions. The Rum Bar is a great place to cool down, enjoy premium cocktails while admiring the Inn’s rich surroundings.
On our stop, the bartender and I believe owner, Helen, solely worked and entertained the room filled with patrons with pizazz and enthusiasm. It was a delight watching her work her charm! I was in awe of how she managed it all so effortlessly.
She was well versed on her rums, greeted all locals in the bar by name, and made a point to acknowledge all incoming tourists by their names as well. The whole experience: the service, welcoming vibe, and drinks were just divine.
The Rum Bar is the neighborhood place we all know and love. It’s the type of spot you’ll find in The Ultimate Key West Bar Guide, order a few drinks, chat up strangers —and the bartender —and enjoy a relaxing afternoon.
We sadly had to move on to Mallory Square, but will undoubtedly be back to Key West to hang at this spot again.
Address: 1117 Duval Street, Key West, FL 33040
10. Sunset Celebration at Mallory Square
The square features a sunset celebration every single night, with live entertainment, food, craft vendors, and street performers all along the oceanfront to join in the festivities.
Favored by locals and tourists alike, the festivities start about two hours before sunset. Pro Tip: To secure an optimal viewing spot, be sure to make your way to Mallory Square at least an hour ahead.
Address: 400 Wall Street, Key West, FL 33040
Other fun activities to add to your Key West itinerary
11. Dinner at D.J.’s Clam Shack
We topped off our day on lively Duval Street at DJ’s Clam Shack, a quaint, laid back front porch and patio-seating shack with friendly staff and mouth-watering fare.
I’m often left disappointed ordering conch on local menus, but always willing to give an establishment a fair shot. DJ’s clam shack beyond delivered island style—the taste, perfectly portioned conch to dough ratio, quality and flavor.
We ordered what seem like the entire menu: the clams, fresh lobster roll, conch fritters, fried shrimp, and cracked conch. It was a lot of fried food, but fried goodness! Everything was just delicious — lightly battered and fried to perfection.
Address: Location: 629 Duval St, Key West, FL 33040