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Only 144 kilometers separate Key West from Cuba, it’s practically a stone’s throw away – closer to Havana than to Miami! This proximity to the Caribbean makes Key West a unique place: time flows differently here, and the phrase ‘island time‘ is not just a tourist slogan. The island at the very end of the Florida Keys archipelago is a true tropical paradise where you can feel an authentic American-Caribbean vibe without leaving the USA.
Key West is the southernmost city located on the continental United States. The island of Key West is not very large, its length is about 6.4 km (4 miles) and its width is 3.2 km (2 miles) at its widest point.
Why does Key West in Florida attract tourists?
Key West is more than just a tourist spot – you could say it’s simply a state of mind! As far back as the 1930s, Ernest Hemingway wrote that he felt ‘like in another country’ here. Indeed, on this small island that is only 6 kilometers long, there is an atmosphere that you won’t find anywhere else in the United States. This island has always lived by its own rules – literally and figuratively. Situated at the junction of Florida, the Gulf of Mexico, and the Atlantic, it has witnessed maritime adventures, pirate legends, wild parties, and quiet rebellions against the mundane routine.
The “island time” atmosphere and laid-back lifestyle
This is where the American dream turns into ‘Caribbean ease.’ The island lives according to the philosophy of ‘island time‘ – time flows slower here, and everyday life has its unique rhythm. Mornings begin with breakfast among palm trees, the day is filled with leisurely bike rides and casual conversations with residents.
The residents of Key West are known for their sincerity and hospitality. After a short stay, you may feel at home here. Life unfolds without hurry – this is a fundamental element of the local culture. The island has officially embraced the motto ‘One Human Family‘, which declares the equality of all people as members of one family.
This unique atmosphere of tolerance has attracted artists, nonconformists, and anyone longing for a place to be authentic without fear of judgment from others for decades. Key West has become a haven for those who value the freedom to be themselves.
My advice: Set aside your watch for a moment and forget about the tour plan. Just embrace the rhythm of Key West – let this place unveil its secrets to you step by step. The greatest magic of this island lies in the people, details, and moments that happen by chance.
The city of rebels and artists
Key West is also an island of outsiders and artists – here Ernest Hemingway wrote his most famous novels, Tennessee Williams found inspiration, and today their spirit accompanies local painters, poets, and musicians. Key West was also appreciated by President Harry Truman, who regularly escaped here from the pressures of political Washington and recuperated after illness. His famous Truman Little White House still retains the atmosphere of those times – it was here, surrounded by palm trees and the sound of the sea, that the president made important decisions, but most importantly, regained internal peace. In Key West, no one judges if you walk barefoot, have colorful hair, or dance in the street – everything is part of the island landscape.
Even today, Key West retains this rebellious character. Walking the streets, you’ll meet musicians playing on street corners, artists painting tourist portraits, and local eccentrics who add unique charm to the city.
The most important attractions of the island – what is worth seeing?
Mallory Square and sunset performances
Mallory Square is the center of tourist Key West and the location of one of the island’s most famous attractions – the daily celebration of the setting sun (Sunset Celebration). Two hours before sunset, the square turns into a grand open-air theater where jugglers, acrobats, musicians, and various street artists perform.
Practical tips:
Duval Street in the center of Key West
“The longest street in the world”
Duval Street is the most famous street in Key West. Duval Street has the official nickname ‘the longest street in the world’ because it is one of the few streets in the USA that connects two large bodies of water – it runs from the Gulf of Mexico to the Atlantic Ocean. Its length is about 1.1-1.25 miles (approx. 2 km).
Chicken patrol on the street
One of the most distinctive features of Duval Street are wild chickens and roosters, which roam freely on the street, enter restaurants, and ‘beg’ for food. This bird population dates back to the early 19th century when Cuban refugees brought roosters for cockfighting. When Key West banned this ‘entertainment,’ Cubans set all the birds free – and since then, they have been freely parading around the island.
The nicest Walgreens in America!
Strand Theatre on Duval Street is one of the most fascinating transformation stories in Key West – from an iconic 1920s cinema to the most beautiful Walgreens pharmacy in America.
Strand Theatre opened its doors in 1921 during the golden age of cinema. It was designed by renowned architects Kiehnel and Elliott in the elegant Spanish Colonial Revival style, and the theater could accommodate up to 800 viewers – which was a huge number for Key West.
In 2001, Walgreens bought the building, but did something exceptional – preserved the entire original façade, neon marquee, and many interior elements, including marble stairs, parquet flooring, and tiles in the lobby.
Record density of bars and… churches
Key West has more bars per capita than any other city in the USA. Interestingly enough, it also has more churches per capita than anywhere else in the country. This perfectly reflects the paradoxical nature of this place!
A legendary place is Sloppy Joe’s Bar – Hemingway’s favorite hangout, where you can still have a drink in the atmosphere of the 30s. Hemingway not only frequented Sloppy Joe’s but was a regular visitor and close friend of the owner Joe Russell – they fished together and spent evenings conversing over drinks. The writer was part of the legendary group of bar regulars and even helped name it its current name. Sloppy Joe’s is now one of the most important stops on the Hemingway trail in Key West.
Equally characteristic is Captain Tony’s Saloon, famous for its unusual decorations: license plates, bras, and dollar bills hanging from the ceiling.
Captain Tony’s was the original location of Sloppy Joe’s until 1937. When the owner Joe Russell moved his bar to the corner of Duval and Greene Street due to a rent increase, the old location was taken over by Captain Tony, who kept the tradition of hanging various memorabilia.
Tradition “Duval Crawl”
Among tourists, the tradition known as ‘Duval Crawl’ is popular – visiting as many bars on Duval Street in one night as possible. It’s almost an obligatory ‘ritual’ for those visiting Key West.
Museum – Ernest Hemingway Home – for literature lovers
Hemingway House at 907 Whitehead Street is the most popular attraction in Key West. In this two-story colonial house, the writer lived from 1931 to 1939, creating his most famous works, including ‘A Farewell to Arms,’ ‘The Snows of Kilimanjaro,’ and ‘For Whom the Bell Tolls.’
However, the biggest attraction is the resident cats – about 60 cats, half of which have the distinctive trait of having six toes. They are descendants of the cats owned by Hemingway, including the legendary Snow White, a white cat given to the writer by a ship captain. All the cats carry names of famous personalities, continuing the tradition started by Hemingway.
Practical information:
The museum is open 365 days a year. Tickets are only available at the main gate, no reservation needed. A 3% fee is added to all card payments.
Southernmost Point – the southernmost point in the USA
A distinctive, colorful buoy at the corner of South Street and Whitehead Street marks the southernmost point of the continental United States. The monument displays the inscription ’90 miles to Cuba,’ reminding of the close proximity of this Caribbean country. The distance of 90 miles (145 km) is a marketing round-up: it’s 94 miles to Cape Hicacos and 89.9 miles to the uninhabited Cayo Piedras. Therefore, a ’round’ number was chosen that sounds better in promotional materials.
This concrete buoy stands 90 meters north of the true furthest point of land in Key West. The actual point is located on a Coast Guard base and is inaccessible to tourists.
The red-black-yellow palette is reminiscent of the colors of an old Latin American navigational buoy and the friendship between Key West and Cuba – hence the inscription ’90 Miles to Cuba.’ Although Cuba cannot be seen from here with the naked eye, the place holds immense symbolic value and is one of the most photographed spots in the USA.
This is also the ‘end of the road,’ because it is here that the famous US Route 1, which leads all the way to Canada, ends (or begins).
Tip: During peak season, the wait for a photo can be 40 – 60 minutes. ‘Locals’ advise coming at dawn if you’re staying on the island: the sun’s rays perfectly illuminate the buoy, and there are practically no lines then.
Bike lanes and “Conch Republic” architecture
Key West is famous for its unique architecture of houses in the ‘Conch’ style – colorful, wooden buildings with characteristic verandas and shutters. The best way to tour the island is by bicycle – Key West is practically flat, and the availability of bicycles makes it easy to get everywhere on two wheels.
Shipwreck Museum
Key West Shipwreck Treasure Museum is an interesting museum dedicated to the rich history of shipwrecks in Key West, which for centuries made the city one of the richest in the USA.
The museum is housed in a reconstruction of a 19th-century warehouse of the legendary shipwreck salvager Asa Tift and features two floors of artifacts from shipwrecks spanning 400 years of history. Highlights include treasures from Spanish galleons of the 16th-17th centuries and a vast collection of exhibits from the wreck of the Isaac Allerton from 1856 – one of the richest shipwrecks in the history of Key West.
Practical information: The museum at 1 Whitehead Street is open daily from 9:00 AM to 5:00 PM year-round. Visiting takes about 30-50 minutes.
Harry S. Truman Little White House – presidential enclave
Harry S. Truman Little White House is the only presidential museum in Florida and a fascinating piece of American history. This wooden house from 1890 originally served as the quarters for the naval base commander, but it was President Harry Truman who made it famous by spending 175 days during his presidency (1945-1953) here.
Truman returned to Key West 5 more times after his presidency (1957-1969), showing how much he loved this place. He spent nearly half a year of his life here in total!
Truman loved playing poker with cabinet members and foreign dignitaries. The museum still showcases the original presidential poker table, where informal yet important political decisions were made during evening games.
This is where key decisions regarding the Cold War were made, and the house also hosted other presidents: Dwight Eisenhower (who stayed here while recovering from a heart attack in 1955), John F. Kennedy during the Bay of Pigs crisis, and even Jimmy Carter with his family during New Year’s Eve 1996.
Fun fact: During World War I, Thomas Edison lived in this house, conducting research on depth bombs for the US Navy.
Practical Information:
Still an active presidential residence
The Little White House remains an official presidential residence and may be closed to the public on short notice due to official duties. Bill Clinton was the last president to stay here – in 2005 with Hillary.
Historic cemeteries and maritime museums
Key West Cemetery is one of the island’s most interesting and peculiar landmarks, offering a fascinating insight into the multicultural history and eccentric spirit of Key West.
Established in 1847 after a devastating hurricane, the cemetery occupies 19 acres and contains up to 100,000 burials – three times the current population of Key West. It consists of Jewish, Catholic, Cuban, and African American sections, as well as monuments commemorating the USS Maine and the victims of the Cuban revolution.
The cemetery is famous for its witty and moving gravestone inscriptions, such as:
Buried here are, among others, ‘Sloppy’ Joe Russell (Hemingway’s legendary bartender), Ellen Mallory known as the ‘Queen of the Bahamas’, and various pirates and circus performers from the 19th century.
The best beaches on Key West and water activities
Fort Zachary Taylor Historic State Park
Fort Zachary Taylor Historic State Park is a historical monument from 1973 located in the tropical paradise of Key West.
Fort Zachary Taylor was constructed during the tumultuous times of American expansion. Construction began in 1845 and lasted until 1866, over two decades marked by yellow fever, hurricanes, and material shortages. This massive bastion of limestone and granite, with walls 1.5 meters thick and 15 meters high, was designed as an impregnable fortress protecting the southern approaches to the USA.
The fort served the Union during the Civil War and the Spanish-American War, and today hosts the world’s largest collection of Civil War-era cannons. Nearly 200 Rodman, Columbiad, and Parrott guns are a true delight for military history enthusiasts. At its peak, the fort could accommodate up to 800 soldiers with 42 guns positioned on three levels.
Fort Zachary Taylor Beach is considered the most beautiful beach in Key West. It is located within a state park and offers white, coral sands and crystal-clear waters. The entrance fee is $6.50 per car or $2.50 per person on foot.
What Fort Zachary Taylor currently offers
Practical information
Opening hours: Daily from 8:00 AM to sunset (fort closes at 5:00 PM)
Entrance fees:
Address: 601 Howard England Way, Key West
Important practical tips:
Other beaches
Smathers Beach is the longest beach on the island (about 800 meters), with soft, white sand. Located along the main road, it is rarely crowded, with full sanitary facilities and picnic options.
Snorkeling and diving
Higgs Beach offers more space and is popular among families with children due to its shallow waters and nearby playgrounds.
The waters around Key West are a true underwater paradise for diving and snorkeling enthusiasts. Florida Keys National Marine Sanctuary protects some of the most beautiful coral reefs in the USA. Popular snorkeling spots include:
Sunset cruises
Sunset Cruises are a must during any visit. Various companies offer cruises on sailboats, catamarans, or traditional schooners. Most cruises last 2-3 hours and include drinks and light snacks.
Sport fishing
Key West is one of the best places for sport fishing in the USA. The waters are rich with tarpons, bonefish, groupers, and marlins. You can rent a boat with a captain for half a day ($600-800) or a full day ($1200-1500).
Kayaking and paddleboarding
Exploring mangrove islands by kayak is a great way to experience local nature. Tours lead through shallow, emerald waters where you can encounter dolphins, sea turtles, and a variety of colorful tropical fish.
Local transport – getting around the island
Cuisine and nightlife – Caribbean flavors in an American style
Local delicacies not to be missed
Key Lime Pie is an absolute must-have in Key West. It’s the official dessert of Florida, made with key lime juice (small, yellow-green limes), sweetened condensed milk, and Graham crackers. You can find the best at:
Recommendation: If you want gluten-free Key Lime Pie in Key West, definitely choose Kermit’s Key West Key Lime Pie Shoppe – it’s the best place for celiacs and those on a gluten-free diet.
Seafood and fusion cuisine
Being on the island, you must try fresh seafood. Conch (sea snail) is a local specialty – try conch fritters (fried dough balls with conch meat) or conch salad.
Grouper sandwich is another icon of local cuisine – fresh fish in a bun with lettuce, tomato, and tartar sauce.
Cuban cuisine has a strong influence on Key West – try a Cuban sandwich (ham, pork, cheese, and pickles) at places like El Siboney or Sandy’s Cafe.
Best restaurants in Key West
Best hotels in Key West
Key West offers a wide range of accommodations – from exclusive waterfront resorts and private islands to affordable hotels in the city, motels, and campgrounds, ensuring every traveler finds something suitable regardless of budget.
How to get to Key West – road trip through the Florida Keys from Miami
Overseas Highway
Overseas Highway (US-1) is one of the most beautiful driving routes in the USA, leading through the spectacular archipelago of the Florida Keys. 113 miles (192 km) from Key Largo to Key West leads through 42 bridges, the most famous of which is the Seven Mile Bridge – nearly an 11-kilometer crossing over turquoise waters, offering breathtaking views of the Atlantic Ocean and the Gulf of Mexico.
Practical information about traveling from Miami to Key West
Overseas Highway for me is one of the most beautiful road trips I’ve taken in my life. The goal is to reach Key West, but the journey itself is an unforgettable experience, with breathtaking views of tropical waters. Honestly, I find it hard to imagine a more spectacular route in the entire United States.
Bridges and attractions along the way
Hidden gem: No Name Pub on Big Pine Key
If you’re looking for an unusual spot to grab a bite on the Florida Keys, you can’t miss the No Name Pub on Big Pine Key!
No Name Pub has been operating since 1931 (first as a store and bait shop, later as a pub and restaurant). The walls and ceiling of the bar are entirely covered with signed dollars; it is currently estimated that there are over 100,000 dollars. The tradition of hanging dollars started in the 1970s – 80s, initially serving as a way to ‘reserve a table’ by fishermen.
The bar is mainly famous for its homemade pizza from a recipe from around 1960 and is known for its authentic, old-school, unpretentious atmosphere. Finding the bar is a bit tricky – the location and access via Watson Blvd. make the sign ‘You Found It!‘ not coincidental.
This iconic bar has been operating since 1931 and is a true gem for savvy travelers.
Practical information:
A huge surprise for me in this bar was that in the middle of nowhere, they made me a delicious gluten-free pizza!
Alternative ways to get to Key West – improved version
Flight to Key West International Airport (EYW)
Key West Airport offers direct flights from Miami, Orlando, Tampa and many other US cities. Flight time from Miami: about 45 minutes.
Ferry: Key West Express
Key West Express operates from Fort Myers Beach to Key West. The journey takes about 3.5 hours one way. The exact time may vary slightly depending on weather and sea conditions.
Prices range from $85 for small children to $185 for adults (round trip). Prices are lower if purchased at least 8 days in advance.
Bus: Greyhound and FlixBus
Organized tours from Miami
Tours organized from Miami are also available and can be purchased on various platforms. Packages vary, but the basic package includes hotel pickup and return, free time in Key West. Some options have snorkeling, trolley rides, or parasailing.
FAQ – Frequently Asked Questions about Key West
No. Although the island is only 150 km from Cuba, the curvature of the Earth hides the land behind the horizon, so even with binoculars it is impossible to see it.
Yes, definitely – this place combines tropical beaches, rich history (shipwrecks, Hemingway, Truman), a vibrant art scene, great cuisine, and famous sunsets at Mallory Square; the island has a unique, tolerant “come-as-you-are” atmosphere .
The cost of traveling by car (one way) is approximately $20–30 for fuel, plus any bridge and parking fees. You can also take a coach tour or ferry, with prices starting at around $60–80 per person.
The best time is from November to May – it is dry, warm, and there are no hurricanes.
Yes, the island offers many family attractions, quiet beaches, and interesting places to visit for the youngest.
The most convenient ways are by bike, on foot, or by scooter – the island is compact and safe.
Summary: ‘Key West – where the weird and wonderful come to play’
As the locals say: ‘Key West – where the weird and wonderful come to play’ – ‘Key West is where strange and wonderful things happen.’ And indeed, once you’re there, everything seems possible.
It’s a place that leaves a lasting impression. You return from there feeling unsatisfied – as if you’ve left a piece of yourself behind. There, no one is in a hurry, no one judges you, you can just be. This is perhaps what is most missed after returning from vacation.
The first breakfast on the porch, a walk among colorful houses, a conversation with someone random at the bar – every day unfolds here differently than you planned.
And it really doesn’t matter if it’s your first visit to Florida or the tenth – Key West constantly surprises. Maybe this time you’ll come across a concert in the hotel courtyard, perhaps you’ll discover a new bar, or simply spend an afternoon with a book on Fort Zachary beach.
One could say that Key West is a way of looking at the world rather than just a place on the map. You arrive with a carefully prepared ‘must-see’ list, and leave with the feeling that the most important moments were those unplanned.
