Exploring Key West, FL
Note: This post has been updated on August 11, 2024.
TIME NEEDED ON THIS KEY: 3-4 NIGHTS
“FUN Fact”: Key West was called “Cayo Hueso” by the natives, meaning “Bone Cay” in English as it’s said the island was littered with the bones of prior inhabitants, making it feel like a communal graveyard. Despite its “grave” past, it has long evolved into one of the most incredible islands the U.S. could own, and one of the only islands we’d ever consider owning a vacation home in.
The below information is a complete guide of the best places to stay, the top rated places to dine and drink, and all there is to see and do. We’ve also included transportation tips, as well as a summary of the history of this beautiful key!
Jump To:
Where to Stay
Smack in the middle of everything in downtown Key West is Almond Tree Inn, an adults-only inn that has absolutely fantastic ratings and we can see why! Our experience from end-to-end was welcoming, relaxing, and all around, wonderful.
With only 22 rooms on the property, a communal pool and spa, comfortable rooms, and an included breakfast and happy hour, it’s absolutely worth checkin in for a few days.
The Reach
The Reach Resort is just one of a few properties on the south end that has its own small beach. While it doesn’t have great ratings anymore, it offers a lot more peace and quiet than the north end, which is where the cruise ships enter and people stay to party.
other recommendations
H2O Suites - Adults only
Where to Dine & Drink
Banana Cafe
French bistro, popular for breakfast, serving crêpes & other easygoing fare in a low-key setting.
Blue Heaven
Iconic landmark for Floridian-Caribbean cuisine & key lime pie, with a funky setting.
Cuban Coffee Queen
Lively counter-serve coffee stand offers traditional Cuban eats, sandwiches & smoothies to-go. NOTE: They have many gluten-free options!
El Siboney
Traditional Cuban home cooking & house-made sangria in a casual, family-friendly setting.
Green Pineapple
The Green Pineapple is a collection of sustainable and eco-conscious Key West boutiques, including a wellness café and yoga studio on upper Duval Street.
NOTE: We absolutely LOVE this boutique/cafe concept and really enjoyed the food. If you have Celiac, this is the place to go! Their cauliflower flat breads and gluten-free pastries are amazing. Even more amazing, is their boutique area!
Hot Tin Roof
Charming seaside eatery with open-air patios serving up a menu of Latin American-style small plates. Make sure to book a month in advance as they have one of the best views of the Key west sunset!
La Te Da
This is a beautiful french bistro/Bed & Breakfast that we highly recommend you at least have brunch at. When you walk up the stairs and into the veranda, you immediately feel like you're in a hidden house in the Hamptons. Everything is luxurious, private, yet comfortable. You feel as though you are having breakfast on someone's patio, overlooking the exotic pool in the middle of the property. The staff there was so wonderful and warm, even furthering your experience there.
Latitude’s Restaurant
NOTE: They have a boat tender that you must take to get to the restaurant. The time of your reservation is the time you will leave the dock (though they ask you to be there 8-10 minutes before your departure).
TIP: If it rains, they will NOT reseat you if you are seated outdoors. If you see what looks like a storm headed your way, reschedule the reservation for another evening or call ahead to request an indoor table.
Moondog Cafe
Relaxed garden cottage offering separate menus for breakfast or lunch & dinner, as well as drinks.
NOTE: We have eaten here twice - once for dinner and once for breakfast. Their food is really good, especially their pastries. If you have Celiac, you will love the rather extensive list of pastries you are able to choose from. My recommendation: The mini key lime pie!
Nine One Five
Stylish old house with a big patio for globally accented American fare, plus a late-night wine bar.
NOTE: I’ve now eaten dinner here twice and both times, I’ve snagged a patio table in the front. Definitely request one if you can and reservations are highly recommended.
Pepe’s Cafe
Rustic joint with laid-back vibes dishing up signature breakfasts plus surf 'n' turf since 1909.
Santiago’s Bodega
Serving tapas, sangria, and wines in quirky mix of decor, mismatched chairs, custom art and reclaimed wood, all coalesced as if it was meant to be.
Sloppy Joe’s
Open since 1933, Ernest Hemingway used to frequent this place every single day and/or night. He loved it so much that when they were moving locations and selling everything in the old place, Hemingway bought one of the urinals and turned it into a fountain (which is to the right of the entrance to the house). Today, this bar offers live music & dancing plus a separate tap room for sports-watching.
Willie T's
Willie T's is a well-known dive bar with two distinct features: 1. The dollar bills tacked to every available wall and ceiling space that have been signed by tourists from all over the world, and 2. The tree that seems to be growing out of the band stage. TIP: Order the key lime frozen margarita.
Things to See & Do
Boating Adventures
Adults only Champagne Celebration Sunset Cruise from Key West
Escape to the still waters off the coast of Key West on this adults-only sunset champagne cruise. Enjoy the peaceful calm of a late afternoon sail on a comfortable catamaran limited to just 14 passengers. Enjoy house champagne, red or white wine, ice-cold beer, a soft drink or bottled spring water, and a gourmet cheese buffet. Then watch as the sun glistens and gently settles into the water, a perfect ending to a perfect cruise.
Corsair 2 Sportfishing Key West
While you’re in Key West, head out on the deep blue waters on this sportfishing charter. The saltwater fishing boat holds up to six anglers, and is rigged with state-of-the-art navigational electronics and safety equipment, outriggers, a fighting chair, a live bait tank, and ice boxes. Plus, it features two private restrooms, a kitchen, flybridge, beds, and air conditioning.
Dry Tortugas National Park Day Trip by Luxury Boat: Axopar 37 XC
Enjoy the Thrill of the open sea and the comfort of top class amenities, ideal for sunbathing, sightseeing or simply relaxing with your group. Escape to the secluded islands and tropical beaches off the coast of Key West on this guided, full-day adventure with History buffs and outdoor enthusiasts alike will love this unique voyage.
Half-Day Cruise from Key West with Kayaking and Snorkeling
Choose from a morning or afternoon excursion and set sail. Kayak through a maze of mangrove-canopied canals and streams, home to a tropical array of birds, rays, sharks, sport fish and more. Then jump into the water for a snorkeling session above a coral reef with 600 different species of marine life. Relax, feel the warm sea breeze and enjoy the day. Snacks, beer, wine, sodas and water included.
Kayaking Through the Key West Mangroves
Along with an experienced guide, you will take a leisurely paddle in shallow, calm, blue-green waters through mangrove tunnels of the Key West backcountry.
Parasailing
Go parasailing above the emerald waters of Key West for a thrilling 1-hour tour that provides sweeping views of Florida’s southernmost city and its surroundings. Head out in a 12-passenger state-of-the-art parasailing boat out to the ocean, then your guide secures you into a double or triple-person parasailing device for a ride that gently lifts off and glides above the water, all without getting wet.
Schooner Sunset Sail with Food and Drinks
Watch the sunset over Key West from the deck of the elegant 105-foot schooner America 2.0 and sit back, relax, and see some of the top sights of the area.
Small-Group Key West Sunset Sail with Wine
Enjoy the scenery and peaceful calm of a late afternoon sail on board a 65-foot schooner. Sample up to eight different wines and/or five different beers. Also included is a gourmet cheese buffet and other appetizers, like summer sausages, water crackers with brie, green apples with a honey drizzle and more. Then watch as the sun glistens and gently settles into the water, a perfect ending to a perfect cruise.
Day Trips
Dry Tortugas National Park
Dry Tortugas National Park is an American national park, located about 68 miles west of Key West in the Gulf of Mexico, in the United States. The park preserves Fort Jefferson and the several Dry Tortugas islands - the westernmost and most isolated of the Florida Keys. The archipelago's coral reefs are the least disturbed of the Florida Keys reefs.
The park is noted for abundant sea life, tropical bird breeding grounds, colorful coral reefs, and shipwrecks and sunken treasures. The park's centerpiece is Fort Jefferson - an unfinished for that is known for having the largest brick masonry structure in the Western Hemisphere (it’s composed of more than 16 million bricks).
Today, activities at the park include snorkeling, picnicking, birdwatching, camping, scuba diving, saltwater fishing, and kayaking. Overnight camping is limited to eight primitive campsites at the Garden Key campground, located just south of Fort Jefferson.
HOW TO GET THERE: The park is accessible only by seaplane or boat.
Historical Exploration
According to their website, “In October 1846, a powerful hurricane bore down on Key West, damaging or destroying nearly all of the homes in the city. In the aftermath of this devastating storm, Captain John Huling Geiger, a harbor pilot and master wrecker, began construction on a grand home that would serve as his family’s residence. Today, that home is known as the Audubon House.”
The Geiger family lived in that house for nearly 110 years, the last of the descendants, a great-grandson, Captain William Bradford Smith, being a recluse for over 20 years. He lived there with no electricity, running water, or an indoor kitchen. Upon his death in 1956, the home had fallen into disrepair and was completely shuttered up. Two years later, the house was slated for demolition until Mitchell and Frances Wolfson stepped in to save it. The home’s large scale restoration was the first of its kind in Key West, which sparked Key West’s restoration movement.
Today, the home, as well as its gardens, are open to tours.
Fort Zachary Taylor
The street that leads to Ft. Zachary Taylor is military housing, which, of course, opens to the Naval base. When you veer left at the guard gate, you feel as though you're trespassing but in fact, you're beginning a 1.25-mile trek to the fort. When you arrive, it doesn't look like much of anything as most of it is in horrible disrepair (due to batteries, canon balls, and other ammunition stored until 1970). What is of interest are the canon windows and what you see on the other side of them - some hold beautiful views.
TIP: There is a hidden beach on the other side of the pine tree forest - it’s a public beach and well worth the trek!
Harry S. Truman Little White House
Perhaps one of the most famous homes with a long list of notable events is the Harry S. Truman Little White House. The house was originally waterfront when it was built in 1890 as the first officer's quarters on the U.S. naval station. In 1911, the building was converted into a single-family dwelling to house the base commandant during which time, additional land was filled in front of the house (eventually, a new building occupied that land, blocking the view).
The first President to visit the site was William Howard Taft, in December 1912. He arrived by Flagler's Overseas Railroad and stayed in Key West before sailing to Panama to inspect the construction of the canal. During World War I, Thomas Edison resided in the house for six months while donating his service to the war effort, during which he perfected 41 underwater weapons. The house remained command headquarters through World War II.
In November 1946, President Harry S. Truman had just finished 19 months in office with no downtime. His doctor recommended a vacation, which is how he came to establish Key West as his second working home. He visited every November–December and every February–March during his tenure and with the aid of technological advances, he was able to communicate with multiple political or world leaders at one time, and also summon staff to Key West for a meeting (since it’s only a three-hour flight). Most importantly, Truman realized that where the President was, the White House was. Documents issued from the Little White House read "The White House, US Naval Station, Key West, Florida." Truman spent 175 days of his presidency at the Little White House.
Notable events after that time:
1946 - 1952 - Cabinet members and foreign officials were regular visitors for fishing trips and poker games.
1948 - James Forrestal met with the Joint Chiefs of Staff to hammer out the creation of the Department of Defense. This was called the Key West Agreement.
1955 - 1956 - President Dwight D. Eisenhower stayed there to recuperate from a heart attack.
1961 - 1962 - President John F. Kennedy and British Prime Minister Harold Macmillan held a one-day summit at the house in March 1961. The President made a second visit in 1962, immediately following the Cuban Missile Crisis.
1974 - The house served as the Naval Station’s commanding officer’s quarters until March 1974, when the submarine base was closed due to the Navy's conversion from diesel to nuclear submarines. It was then added to the U.S. National Register of Historic Places.
1987 - The House was deeded to Florida and held in a trust as a public museum.
1990 - Nearly $1M was spent to restore the home to its 1949 appearance.
1996 - Former President Jimmy Carter had a family reunion there.
2001 -Secretary of State, Colin Powell, opened a week of OSCE peace talks, led by Minsk Group Co-Chairman, Carey Cavanaugh, between President Robert Kocharyan of Armenia and Heydar Aliyev of Azerbaijan.
NOTE: Today, you can tour the house exactly as it was in 1949, and it’s totally worth it. However, you are not allowed to take pictures inside.
Hellings Curry Museum Home of The Key West Women's Club
One of just a few brick structures in Key West, the 8,334 square foot mansion was built in 1892 by Captain Martin Luther and Eleanor (Curry) Hellings. Eleanor was the 6th child of 8 born to William and Euphemia Curry, one of Key West’s foremost merchants and Florida’s first millionaire.
Mr. William Curry understood the importance of getting families back to work and would do whatever he could to keep his own family in Key West. He generously gifted each child $10,000.00 to buy land, fund a new home, or expand an existing home. Shipbuilders now became house builders.
Hemingway Food and Walking Tour
Follow in the footsteps of Ernest Hemingway during a walking tour that focuses on food, culture, and history. Exploring Key West on foot means that you'll get a more intimate glimpse into the historic area, which is characterized by its charming bars and plethora of museums. Plus, you'll receive personalized attention as you explore in a small group limited to only 15 other travelers. Lunch, snacks, and some alcoholic drinks are included.
Hemingway House
In 1931, Hemingway and his wife, Pauline, moved to Key West, upon her Uncle Gus purchasing the Spanish home for them. For the next eight year years, they continued to inhabit and decorate the expansive dwelling, including adding a $20,000 pool in the late 1930s, much to his dismay. The area previously held Ernest’s boxing ring. It was the final straw before their divorce in 1939.
The first thing you notice about the house are the 360-degree wrap-around porches on the first and second floors that gave views of the street, the pool, and the hidden gardens. Once you enter the home, the first floor seems small and narrow with grand paint colors and decor. It goes from Southern-style mansion on the outside, to Euro-colonial on the inside with just one step. However, the most fascinating of rooms on the first floor was the kitchen. Given that it was built in the 1930s, it has one of the most advanced kitchens of that time, including a stove, oven, refrigerator, and dishwasher.
When you head upstairs, you notice how dark it seems and how again, so many of the rooms seemed so narrow, given the enormous exterior. Since it was mostly just the two of them, they had one bedroom (where two of his legendary cats live), a dressing room (with fireplace), and a true 1930s bathroom that has never been remodeled. However, what I loved most about the house was that almost every room on the second floor had double french balcony doors leading out to the porch.
Heading out through Hemingway's bedroom, we took the back stairs to his detached office. Considering this is where he spent the bulk of his time, it was almost surreal to see it.
If that wasn't enough, the backyard and guest house (now public bathrooms) completed our historic home tour.
FUN FACT: As of 2024, there are 59 cats, many of which have come from lineage breeding from the 6-toed line. This means many of the kitties have 6 or 7 toes on one paw!
Jimmy Buffet Tour
If you have a passion for all things Buffett and Margaritaville, this walking tour is the best way to find the locations around Old Key West that inspired his songs. Your guide will also take you to the location of his first gig, some of his favorite watering holes, bars he played in and his recording studio.
Key West Cemetery
In 1847, Key West Cemetery was established at its current location after an 1846 hurricane washed dead bodies from the earlier cemetery out of the coastal sand dunes on Whitehead Point, near the West Martello Towers. An African Memorial Cemetery was dedicated beside the West Martello Tower in 2009. Slaves, ill from the sea voyage to slavery in "The New World," were buried there prior to the US Civil War.
In 2005, the cemetery was among those profiled in the PBS documentary A Cemetery Special.
Key West Museum of Art & History at the Custom House
Originally home to the island’s customs office, postal service, and district courts, this four-story architectural marvel was built to keep pace with the increasing population and wealth accumulating from Key West’s lucrative trade routes and maritime industries. The Custom House was eventually leased to the Key West Art & Historical Society for use as a museum. Today, “Old 91” has been faithfully restored and stands on the harbor as a national landmark, an award-winning museum, and official headquarters of the Key West Art & Historical Society. Experience two floors of exhibitions that weave together two centuries of history, art, people, and events.
NOTE: This is one of the more “hidden gems” in Key West that many people choose not to go see. Not only is there some great, thought-provoking art, but there are a few Hemingway artifacts, as well as 1930s artifacts that bring to life what it was really like in that time period.
Key West Lighthouse
The first light house was completed in 1825 with Michael Mabrity the keeper of it until he died in 1832. His wife would go onto be the keeper for the next 32 years.
The Great Havana Hurricane of 1846 destroyed the lighthouse. The USS Morris, which was wrecked during the storm, reported "a white sand beach covers the spot where Key West Lighthouse stood". Barbara Mabrity survived, but 14 people, who had sought refuge in the lighthouse tower, died, including seven members of her family. Barbara Mabrity continued to serve as keeper of the Key West Light until the early 1860s, when she was fired at 82 years of age for making statements against the Union.
It wasn’t until 1848 that the new tower for the Key West Light was completed. Initially, it was 50 feet tall with 13 lamps in 21-inch reflectors, and stood on ground about 15 feet above sea level. In 1873, the lantern was replaced (it had been damaged by a hurricane in 1866), adding three feet to the height of the tower. The growth of trees and taller buildings in Key West began to obscure the light and in 1894, the tower was raised 20feet, placing the light about 100 feet above sea level.
In 1969, the Coast Guard decommissioned the Key West Light, turning it over to Monroe County, who leased it to the Key West Arts and Historical Society. The society operates the lighthouse and its associated buildings as the Key West Light House and Keeper's Quarters Museum. On display at the museum is the first-order Fresnel lens from the Sombrero Key lighthouse.
TIP: If stairs and/or heights are not your thing, don’t make the trek as it’s 100 ft. of narrow, spiral stairs. If you are able to, the views at the top are worth it!
The oldest house in Key West was originally located a block or two away on Whitehead Street. It has weathered hurricanes, fires, and the harsh marine environment. Its resiliency is largely due to the skill of Captain Richard Cussans, a ship's carpenter who built the house.
The expansion of the city, from its deep-water port beginnings, was slowed by the existence of a natural salt-water pond that ran from Whitehead Street through the old city hall site to the port. By 1829, a large portion of the lake had been filled and the house was moved to its current location.
The house was enlarged to four rooms with a center hall to accommodate its next residents, Captain Francis Watlington, his wife Emeline, and their nine daughters. Captain Watlington held a number of maritime positions in his career, including pilot, port warden, wrecker, Coastal Pilot for the U.S. Navy during the Second Seminal War, and the Inspector of Customs. One of his duties for the Customs Office was to oversee the "light ships," vessels that were used as floating lighthouses at dangerous coastal and reef locations. He served in the Florida House of Representatives from 1858 to 1861 only to resign his office at the outbreak of the Civil War. He joined the Confederate Navy in Mobile, Alabama, and served as the captain of the gunboat Gaines of the Naval Squadron. With the Union victory in Mobile, Captain Watlington surrendered in May of 1865 and was paroled shortly after. While he returned to Key West, and he did not live in the home until his wife passed away in 1869. Since then, his family and descendants lived in the house until the early 1970's.
West Martello Tower and Key West Garden Club
According to their site, “The Key West Garden Club at West Martello Tower is a tropical garden paradise by the sea on the site of a former Civil War fort. It has garden rooms to delight you, history to intrigue you, and the beach and sea to inspire you.”
Unique Experiences
Located at 301 Whitehead St., on the corner of Whitehead and Caroline, stands one of Key West's most impressive and historic buildings – First Flight. Well known for being the birthplace of Pan American World Airways, Pan-Am's first tickets were sold out of this very building in 1927. Today, it’s a brewery with a touch of nostalgia.
Key West First Legal Rum Distillery
Per their site, “We're all about soaking up the rich history and flavors of Key West. With each batch of salt-cured rum, we've captured the very essence and rebellious spirit of this sun-kissed paradise. After all, we advocated to change the law and were the first to legally distill and sell liquor here. And isn't it just fate that our rum distillery found its home in a former Coca-Cola Factory? Rum and Coke - it was meant to be!”
Their building, itself, was built in 1900 for Jack’s Saloon. Three years later, in 1903, the building was converted into Coca-Cola bottling facility. While only used for a short period of time in this manner, it later was used as office space, upscale clothing shops, liquor distributors, and a short run as a key lime pie factory. Since 2012, it is now Key West’s first rum distillery.
TIP: Get the piña colada with the key lime rum topper and definitely do a tasting!
NOTE: You can legally drink the drinks served while walking around Key West!
Key West Shipwreck
Although the admission price seems high, the experience is worth it. There is a very "animated" tour guide who pretends to be a shipwrecked captain, showcasing everything that had been pillaged from these wrecked ships that sank right off the coast. Each and every artifact in the museum was a rescued good, including a 60-pound silver bar that sank not once, but twice. It was quite amazing what had been recovered, including a maiden from the front of a ship, bales of cotton, wine, gold, silver and other amazing treasures.
I headed up the shipwreck tower to get yet another view of the island. As a reward, I went down to the only basement on the island (one feet below sea level) to sit and see the video on why this museum is so important. According to the video, when someone yelled "shipwreck ashore" people dropped what they were doing to recover the items that floated onto the beach - it became a source of income for them.
Mallory Square
As the official sunset square of Key West, each evening, the square comes alive with a large variety of talented musicians, sword swallowers, jugglers, escape artists, animal acts, acrobats, and tightrope walkers.
Southernmost Point Buoy Marker
The large painted buoy was established as a tourist attraction in 1983, by the city, at the corner of South Street and Whitehead Street. The concrete buoy has overall withstood several hurricanes and is a gathering place for photographs and tourists.
TIP: If you want a great picture of it, go in the earlier side of the morning before the tourists make their way down there.
THE KEY WEST BUTTERFLY & NATURE CONSERVATORY
The Key West Butterfly and Nature Conservatory is a butterfly park that houses from 50 to 60 different species of live butterflies from around the world, in a climate-controlled, glass-enclosed habitat.
The conservatory includes flowering plants, cascading waterfalls and trees. There are also several species of free flying "butterfly-friendly" birds, such as American flamingoes, red-factor canaries, zebra finches, cordon-bleu finches, and "button" or Chinese painted quail.
Walking Tours
Built between 1932 and 1934, the Key West Aquarium is one of Florida's oldest aquariums and initially, only charged 15 cents for adults and 5 cents for children to enter.
The aquarium was conceived by Dr. Robert Van Deusen, the Director of the Fairmount Park Aquarium in Philadelphia. It was originally an open air aquarium, one of the first and largest at the time.
During the Great Depression, Key West turned over its charter to the federal government, due to the economic disaster that hit the island. The federal government believed that Key West's weather and location would make it an ideal tourist destination. The Works Project Administration (WPA) was sent in and built the tourist attraction.
Today, it’s not worth visiting at all, though the ticket purchase price does help keep the few aquatic inhabitants alive.
The Shops at Mallory Square
The Shops at Mallory Square are located in one of Key West’s most historic structures. Building 1, as it was designated on the Key West Naval Station, was built between 1856-1861 and served as a coaling depot, sail maker’s loft, and is now a 26,000 square foot emporium that has Key West’s only up escalator. The Shops at Mallory Square feature some of the island’s most interesting shops, boutiques, art galleries, exhibits, and places to eat.
Walking Around Town
Walking Food Tour With Secret Food Tours
Discover the very best bites on a gourmet tour that samples a little bit of everything, exploring Key West’s charming neighborhoods, colorful characters, and history along the way.
How to Get There
Rent a car and drive from Miami!
While there is a local airport, for those that have driven down to Key West, know that it is THE OPTIMAL way to go!
HOWEVER, did you know there’s a more scenic route through the Everglades that far surpasses being stuck on a concrete highway the whole time?
Take U.S. Route 1 through Miami until you come to the intersection of U.S. 1 and Card Sound Road. Turn onto Card Sound Road and follow it the whole way into Key Largo. There are lots of marshes, hidden beaches, trees, and government-restricted areas (and probably plenty of alligators).
Point of Interest: Right before the toll/bridge, you will see a biker bar called, “Alabama Jacks”. Depending on the time of day you get there, you may want to stop in for a drink.
Once past the toll, it opens to the first bridge, Caribbean water, and plenty of sunshine. You're then surrounded by paradise all the way to Key West.
Need a food stop on the way? Head to Midway Cafe!
Midway Cafe is the halfway point between Miami and Key West (in Islamorada) and provides a great stop for some great food. They are VERY gluten-free friendly with some wonderful gluten-free desserts, wraps, sandwiches, and more.
Transportation on the key
Unless you plan on leaving Key West for the day, you really won’t need your car - parking is at a premium anyway. There are plenty of pedicabs and Ubers available, though Duval street is walkable from end to end.
A History Summary
18th century - The last Native American residents of Key West were Calusa refugees who were taken to Cuba when Florida was transferred from Spain to Great Britain, though nothing came of their possession.
1821 - The Spanish governor of Cuba deeded the island of Key West to Juan Pablo Salas, an officer of the Royal Spanish Navy Artillery, posted in Saint Augustine, Florida. He sold it to John Simonton for $2000 pesos upon the U.S. acquiring Florida however, it was commandeered by Lt. Commander Matthew C. Perry (you read that right) who sailed the U.S.S. Shark to the island, planted a U.S. flag, and claimed it as belonging to the U.S.. Nobody fought him on that.
1823 - Commodore David Porter of the U.S. Navy West Indies Anti-Pirate Squadron took charge of Key West, which he ruled as military dictator under martial law. The United States Navy gave Porter the mission of countering piracy and the slave trade in the Key West area.
1830 - 1861 - Key West was a major center of U.S. salt production, harvesting the commodity from the sea (via receding tidal pools) rather than from salt mines. It was shut down during the outbreak of the Civil War.
1845 - 1866 - Fort Zachary Taylor was constructed - an important Key West outpost during the Civil War.
1846 - Key West suffered major damage from the Havana Hurricane.
1852 - The first Catholic Church, St. Mary's Star-Of-The-Sea, was built.
1860s - 1870s - During the Ten Years War, many Cubans fled to Key West, which mean several cigar factories came with them. Suddenly, Key West was the largest producer of cigars in the world.
1864 - Five Sisters of the Holy Names of Jesus and Mary arrived from Montreal, Canada, and established the first Catholic school in South Florida. It is still operating today and is now known as, “Mary Immaculate Star-of-the-Sea School”.
1886 - A fire started at a coffee shop, next to the San Carlos Institute, and spread out of control, destroying 18 cigar factories and 614 houses and government warehouses. Despite many factories moving to Ybor City in Tampa, Key West was still Florida’s wealthiest city.
1909 - 1910 - Key West was devastated by the 1909 Florida Keys hurricane. Further damage was suffered the following year in the 1910 Cuba hurricane.
1912 - Key West was relatively isolated until it was connected to the Florida mainland, via the Overseas Railway extension of Henry M. Flagler's Florida East Coast Railway.
1919 - Florida Keys hurricane caused catastrophic damage to the city.
1926-1927 - Pan American Airlines was founded in Key West, originally to fly visitors to Havana. The following year, the U.S. Postal Service contracted them out to deliver mail to Havana.
1935 - The Labor Day Hurricane destroyed much of the Overseas Railway and killed hundreds of residents, including around 400 World War I veterans who were living in camps and working on federal road and mosquito-control projects in the Middle Keys. The FEC could not afford to restore the railroad.
1938 - The U.S government rebuilt the railroad as an automobile highway, which is built atop many of the railroad footings and is an extension of U.S. Route 1.
1946 - Harry S. Truman established a working vacation home (Harry S. Truman Little White House). He spent 175 days of his presidency working from there.
1959 - Ferry operations between Key West and Havana ceased.
1982 - In 1982, the city of Key West briefly asserted independence as the “Conch Republic” as a protest over a United States Border Patrol blockade. This blockade was set up on US 1, where the northern end of the Overseas Highway meets the mainland at Florida City. A traffic jam of 17 miles ensued while the Border Patrol stopped every car leaving the Keys, supposedly searching for illegal immigrants attempting to enter the mainland United States. To this day, flags and other souvenirs are still sold and each year, there’s a parade to commemorate the day.
2017 - Hurricane Irma caused substantial damage with wind and flooding, killing three people.
