Few places on U.S. soil will give you that Caribbean feeling like the Florida Keys. Driving across the first causeway to Key Largo leaves one world behind while you “dive” into another. With over 800 islands stretching 180 miles, you will find a favorite, but you will enjoy them. Driving the Florida Keys is something everyone should do at some point.
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Disclosure: some of the links below are affiliate links. If you purchase a linked item, we will make a commission, at no extra charge to you.
Key Largo
After crossing the causeway you come into Key Largo. We made our first stop at Alabama Jack’s, a small roadside fish shack. It was a recommendation we say during a Jimmy Buffet interview and who knows the Keys better than Buffet. The interview recommended we try the conch (pronounced con-k) fritter. And it was the best we had while in the keys (by far)! (Lesson: Jimmy knows the Keys and conch.) A little unsettling to recent Floridians was the placement. Our waterside table offered great views and a sign that warned the water was a crocodile reserve.
Traveling further into Key Largo, we stopped at our RV park (Key Palms RV Park). The RV park was next door to the World Famous Caribbean Club. The club was made famous in the Humphrey Bogart movie Key Largo. Both were prime sunset viewing locations!
African Queen
While visiting Key Largo, you can view the iconic vessel made famous by the Humphrey Bogart and Kathrine Hepburn 1951 movie, African Queen. The steamboat remains a timeless classic and still offers daily cruises along the Port Largo Canal.
The African Queen was built in Lytham, England in 1912 for service in Africa by the East Africa British Railways. After starring in the 1951 movie, she arrived in the United States in 1968 to work in San Francisco, Oregon, and Florida. The famous vessel arrived in Key Largo in 1982, where she is registered as a National Historic site.
Islamorada
Stretching from mile marker 90 to 72, Islamorada is known as the Sport Fishing Capital of the World. With several stops, you may want to grab a spot in Islamorada or Key Largo to stay a few days.
History of Diving Museum
You don’t have to be an avid diver to appreciate this stop, but you may leave ready to get certified. The museum walks you through the entire history of diving with an extensive collection of diving gear.
John Pennekamp Coral Reef State Park
There isn’t a lot to see in this state park unless you book a boat or diving trip. Most of the tours will leave from the park including the scuba and diving trips to view Christ of the Abyss.
Islamorada Brewery & Distillery
On a key said to be a drinking town with a fishing problem this stop is a must and won’t disappoint you. They brew craft beer while distilling island rum, vodka, and gin. The flights include their frozen drinks and beer. Don’t forget to grab their frozen drink pouches for the rest of your trip!
World Wide Sportsman – Pilar
Even if you don’t need last-minute sportsman equipment for your trip, this is a stop worth making if you are an Ernest Hemingway fan. Dry-berthed in the store is a vessel called the sister ship to Hemingway’s Pilar. The original is in Cuba, but you will not be allowed inside it. The sister ship allows you to climb aboard to see how Hemingway sailed.
Hurricane Memorial
A monument to the 408 people killed in the Labor Day 1935 hurricane. This is unlikely to be a stop many guides mention, but it is worth a few minutes of your time. The hurricane was not just strong for the season. But has been classified as one of the strongest to ever hit the United States. Rated at a Category Five on the Saffir-Simpson Hurricane Scale, it was the first of three Category fives to hit America in the 20th Century. The storm started weak in the Bahamas and developed quickly. Leaving little time for evacuations. The Florida Overseas Railroad was sent to evacuate people. But the storm surge hit the railway around Upper Matecumbre and knocked it from its’ tracks.
The monument is carved from local coral limestone and erected on November 14, 1937, at mile marker 81.5.
Marathon Key
The Turtle Hospital
It may seem strange to stop at a veterinary hospital, but it is a popular stop for marine life lovers. Opening in 1986 with a desire to help sea turtles, the organization holds true to its origins at mile marker 48.5. The Turtle Hospital has rehabilitated and released more than 1,500 sea turtles since its opening.
Cracked Conch Cafe
You will have wandered past a few places selling conch at this point. The Cracked Conch is a bit different though. You will hear them pounding the conch to tenderize it and the dishes are not your typical seafood joint. Conch Eggs Benedict, Conch Picatta, Conch Marsala, Conch Parmesan, and more fill this menu.
Seven Mile Bridge
This is it. This is the bridge you have seen in so many photos of the Florida Keys. Finished in 1982, this is the longest bridge in the Keys. This bridge replaced the still visible and narrow 1912 bridge. The old structure was originally a railroad bridge and known as the “Eighth Wonder of the World.” It got its’ nickname because building something that long, in soft sand and a tropical environment was quite the task.
The bridge was built by Henry Morrison Flagler an oil tycoon building a railroad to Key West. It was the same railroad washed off its tracks by the hurricane’s storm surge (above). But in 1908, Flagler held fast to his dream to complete his railroad. Spending $30 million of his fortune before opening the bridge on January 28, 1916. Upon stepping out of the first car in Key West, Flagler said, “Now I can die happy. My dream is fulfilled.”
Along the old bridge, you will see a random tree growing. Lore has named it Fred.
Big Pine Key
A popular stop on this key is No Name Pub (https://nonamepub.com/). The directions will have you winding through neighborhoods. Watch out for Key Deer. Arriving at a once small building displaying a “you found us” sign. The popularity has caused a few expansions. The bar is not dog-friendly.
Keys locals are called conchs. However, you don’t become a conch by simply moving to Key West. If you’ve been a resident for at least seven years, some might consider you a “freshwater conch”. A “saltwater conch” refers to a person born in Key West.
Visiting Key West
Key West is one of those destinations you need to experience. This small 2-mile by 4-mile island is jam-packed with adventure! So here are a few things you don’t want to miss when visiting the island.
Key West Facts:
- Spanish explorer Juan Ponce de Leon found Key West in 1513 by mistake while searching for the Fountain of Youth.
- The 1803s locals made money by salvaging and auctioning shipwrecks. By 1889, Key West was the biggest and wealthiest city in Florida and the richest per capita in America.
- Key West is closer to Cuba than Miami. Cuba is 90 miles away while Miami is 150 miles from the city.
- Key West is connected to the mainland with 42 bridges and one of the most beautiful scenic drives in the United States, the Overseas Highway. The construction of the 113-mile-long concrete road finished in 1938. The longest bridge is the suitably named Seven Mile Bridge.
- On April 23, 1982, Key West declared secession from the U.S.A. The move was a protest against the US Border Patrol checkpoint at the entrance of US 1 (Overseas Highway). The checkpoint would be a major inconvenience for tourists trying to access the island resulting in traffic jams that were 17 miles long. They still celebrated annually with the Conch Republic Independence Celebration.
- Chickens have roamed the streets for decades.
- Key limes are no longer harvested in Key West. The produce for your favorite pie is now imported from Mexico, India, and the West Indies.
- Key West has inspired more writers per capita than any other (American) city. Famous authors who called Key West home include Ernest Hemingway, Tennessee Williams, Shel Silverstein, Robert Frost, Philip Burton, Judy Blume, and Elizabeth Bishop.
- The Atlantic Ocean and the Gulf of Mexico meet at Key West. Key West’s diverse and unique ecosystems are a result of the convergence of the Atlantic Ocean and the Gulf of Mexico.
- Key West is home to the third-largest barrier coral reef. The Florida Reef reaches 170 miles from Miami to the Dry Tortugas and is about four miles wide while housing 1,400 species of marine plants and animals.
- Key West consists of several islands. Dredgers Key, Fleming Key, Sunset Key, Wisteria Island, and the northern part of Stock Island are included in the city of Key West.
Southernmost point – Corner of South Street and Whitehead Street
Established as a tourist attraction in 1983. The anchored concrete buoy marks the southernmost point in the continental United States. It is one of the most visited and photographed attractions in the United States. Go early to beat the line! The line for a photo can wrap around the block. Going early we had the area to ourselves.
Mallory Square
The area houses gift stores and restaurants. Near sunset, the street performers come to entertain tourists during the nightly “sunset festival.” Every sunset is a reason for celebration in Key West. You can watch the impressive performers and cheer the orange glow of the sun dipping below the horizon. Don’t forget to tip your performers.
Near the square is a portable stand called Key West Original Conch Fritters. They offer great conch fritters for your sunset festivities. (Try the Key Limeade too)
Shrimpboat Sound (Jimmy Buffet’s recording studio)
Wandering Key West you may find an ordinary white building covered with stickers on the Key West Historic Port. This unassuming building holds an interesting history for fellow Parrotheads. It is the studio Jimmy Buffet has recorded most of his music inside. Not a Buffet fan? When he is not using the studio, he loans the studio out to other musicians to be inspired by Key West. Known to use the studio are artists such as Alan Jackson, The Eagles, Zac Brown, George Strait, Toby Keith, and Kenny Cheney.
Cuban Queen Coffee
Grab your pick-me-up at this walk-up window around the corner from Jimmy’s studio. A small food menu complements the amazing coffee. The nearby sticker-covered truck is said to be Jimmy’s too. Another photo opportunity is the side of the building with a “Greetings from Key West” mural.
Hemingway’s House in Key West
The residence of Ernest Hemingway in the 1930s the house is located at 907 Whitehead Street, across from the Key West Lighthouse. Ernest is rumored to have used the lighthouse to find his way home after a night at Sloppy Joe’s bar. (The original Sloppy Joe’s was located in the space now occupied by Captain Tony’s Saloon.)
Ernest and his wife Pauline Pfeiffer moved to Key West in 1928. When Pauline first saw the home, she labeled it a “danced haunted house.” The home was in deep disrepair after sitting empty at the time. Seeing the potential, she convinced her wealthy Uncle Gus to purchase it for her as a wedding present. The Hemingways restored the home and converted the second story of the carriage house into a writing room for Ernest.
Pauline installed the first swimming pool in the Florida Keys while Ernest was reporting in Spain. The 24×60 foot 80,000-gallon pool was expensive ($20,000). Two and a half times the purchase price of the entire property. Ernest did not approve of the costly addition when he returned. He threw a penny from his pocket onto the ground and declared, “You might as well take my last cent.” Pauline had paid for the pool herself, but took the penny and embedded it into the concrete. Despite his early anger Hemingway grew to love the pool.
Hemingway lived in the house for eight years and moved to Cuba following his divorce from Pauline. The house was returned to him after Pauline’s death and remained in his possession until his suicide.
While living in Key West, Hemingway wrote some of his most popular work. Including the 1935 non-fiction work Green Hills of Africa, the 1936 short stories “The Snows of Kilimanjaro” and “The Short Happy Life of Francis Macomber”, and his 1937 novel “To Have and Have Not”. A manuscript was discovered in the garage vault after his death. It was posthumously published in 1970 as “Islands in the Stream”.
There are a few things to be on the lookout for during your visit:
- Your hosts during your visit will be descendants of Hemingway’s cat, Snowball. The cats are polydactyl. Some are friendly. Some are not. After all, cats…
- The fountain in the back is actually a urinal from the old Sloppy Joe’s bar. The story is when the landlord raised the rent causing the bar to move. Hemingway stated he had pissed away enough money in that bar and was taking the urinal. And he did.
Tip: Be sure to bring cash. The tickets are cash only.
Truman Little White House
The building is Florida’s only presidential site and served as the vacation home of Harry S Truman. It was also used by six US Presidents. However, Truman spent the most time here. Totaling 175 days during 11 visits. Key West must’ve offered a welcome escape with all Truman had to deal with during his presidency.
More recently, presidents tend to use Camp David for vacations today, but Secretary of State Colin Powell used the location to facilitate a settlement of the Nagomo-Karabakh conflict.
Fort Zachary Taylor
On the southern edge of Key West sits Fort Zachary Taylor. Predating the Civil War this National Historic Monument housed the largest cache of Civil War armament in the world. You can walk the pathways and grasp how soldiers lived and fought in the Civil War and Spanish-American War.
The park is the southernmost state park in the continental United States and a great place to hit one of the few Key West beaches.
Edward B Knight Pier for sunrise
While Key West holds a celebration for every sunset, the sunrises are equally amazing if you didn’t throw back too many cocktails the night before. We headed out to the pier to watch with coffee in hand and we were not the only ones with the idea.
Kermit’s Key West Lime Shoppe
You cannot leave Key West without having a few slices of key lime pie. While you can find it anywhere, Kermit’s is the most famous for the pie and expanded line of key lime everything! While you probably can’t go wrong with any of the products, make sure to try the chocolate-dipped frozen key lime pie!
Sandy’s Cafe (laundromat)
So, you’re going to drive into the local neighborhood and stop at a laundromat for a sandwich. Yes, I am serious! I promise you will not regret it! The best Cuban sandwich you will ever have! Just the best. We went back multiple times!
Key West Sips
Key West is a drinking island. While bars are plentiful, here are some you don’t want to miss.
Sloppy Joe’s
Possibly the most popular historic bar in Key West, Sloppy Joe’s has been serving drinks since 1937 to some of Key West’s most famous locals. The bar at the corner of Duval is a new(er) location. The Sloppy Joe’s Earnest Hemingway spoke of was located in the location now occupied by Captain Tony’s.
The Green Parrot
Firmly established as a Best Bar of Key West, The Green Parrot. The Green Parrot is a great place to visit after a walk-thru the Hemingway House. The dive bar atmosphere is everything you would expect.
Smallest Bar
At a mere 72-square-feet (about the size of a jail cell), this bar is undoubtedly one of the smallest bars in the world. Be sure to try their Key Lime Shot when you visit!
First Flight Island
Located at 301 Whitehead St (near Truman’s Little White House), this brewery occupies a historic building. The building is the birthplace of Pan American World Airways. The first tickets were sold out of this building.
The company was founded to have mail and passenger service between Key West and Havana. It became credited with many innovations that shaped the international airline industry.
Now you can enjoy some great food and craft brews.
Captain Tony’s Saloon
Just down the street from the current Sloppy Joe’s location, you will find Captain Tony’s. The bar has been patronized by many notable artists, writers, and celebrities. When a celebrity visits, a barstool is painted with their name and placed at the bar. The building has a deeper history than the bar itself. First constructed in 1852, it was the ice house and doubled as the city morgue. During the Spanish-American War, it housed a wireless telegraph station. During this time the news of the Battleship Maine being destroyed was reported here. It became Sloppy Joe’s in the 1930s. Making it the location Hemingway spent most evenings from 1933 to 1937. The bar was moved when the landlord raised the rent. The bar was purchased by Tony Tarracino (Captain Tony) in 1968 and it is this bar that gave Jimmy Buffet his Key West start.
Jimmy Buffet references the bar in his song “Last Mango in Paris.” If you visit, make sure to peek into the men’s restroom to see the handwritten lyrics to the song on the wall.
Legend has it the fish in the sign outside was caught by Tony and preserved. It is said that throwing a quarter into its mouth will bring you good luck until you leave the island.
The Chart House
Only in Key West could a real treasure hunter sit in a motel room-turned-bar, tended by an actual gun-running pirate smuggler, while charting his search for a lost Spanish treasure ship. All the while listening to one of the most influential musicians to ever sing about the Caribbean.
Sounds like a place out of a Hollywood movie? No, just a random hotel room bar. You can read our full article on this unique bar here.
Keep in mind Hurricane Seasonwhen visiting the Florida Keys. The season runs June 1-November 30 with the heaviest storms occurring August-October.
The busiest and priciest time to visit the Keys is winter (November-March).