Key West, Florida

The Conch Republic, better known as Key West, is the southernmost part of the Florida Keys and the Continental U.S. Its charming Old Town is filled with history and surrounded by beaches along the Gulf of Mexico and the Atlantic Ocean.

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1 Mile Marker Zero in Key West, Florida

When you see this sign at the intersections of Whitehead and Fleming streets near the Monroe County Courthouse, you have reached the “end of the road” of the longest north-south interstate in the United States: U.S. Route 1. It begins in northern Maine and travels 2,369 miles along the eastern seaboard until arriving in Key West. Hopefully this iconic sign is there when you arrive. It is one of the most popular road markers in the U.S. to steal. A local t-shirt shop even trademarked the image.

501 Whitehead St, Key West, FL 33040
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2 Monroe County Courthouse Clock Tower in Key West, Florida

Monroe County was named in honor of President James Monroe when it was formed in 1823. It jurisdiction extends over 220 miles of the Florida Keys, making it the southernmost county seat in the United States. Most of its government offices are in Key West such as this County Courthouse. It was built in 1890 and significantly renovated in 2000.

500 Whitehead St, Key West, FL 33040
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3 Mallory Square Signage in Key West, Florida

Above the list of stores and attractions on this sign for Mallory Square is the slogan: “Where the Sun Sets and the Fun Begins.” By day, tourists shop in this Old Town square. As dusk approaches, people line up along the waterfront to watch the sun set over the Atlantic. The daily event is aptly called the “Sunset Celebration.” This party tradition, which began in the late 1960s, is surrounded by musicians, street entertainers and of course food and drink. The square is named after Stephen Russell Mallory. He was the son of Ellen, the first white woman to settle in Key West in 1823. He became a U.S. Senator and Secretary for the Confederate Navy.

400 Wall St, Key West, FL 33040
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4 Key West Shipwreck Museum in Key West, Florida

This wooden, 65 foot observation tower near Mallory Square is a reproduction of the salvaging warehouse owned by Asa F. Tift. He was the most famous and successful wrecker in Key West until he died in 1889. The Key West Shipwreck Museum has exhibits, artifacts, a film and actors telling the story of this fascinating and lucrative industry during its peak in the second half of the 19th century.

1 Whitehead St, Key West, FL 33040
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5 Asa F. Tift Bronze Bust in Key West, Florida

Florida’s coral reef destroyed countless ships; bad news for sailors, great news for 19th century salvagers called wreckers. The best in the industry was Asa F. Tift. He and his crew recovered cargo and, if possible, repaired the vessels. His warehouse was at today’s Mallory Square. Some of his wealth went towards building a mansion on Whitehead Street in 1851. 80 years later it was purchased by Ernest Hemingway. This statue is located in the Memorial Sculpture Garden. The outdoor exhibit includes the likeness of 36 people who shaped Key West’s history.

401 Wall St, Key West, FL 33040
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6 Ernest Hemingway House in Key West, Florida

Ernest Hemingway and his recently married second wife Pauline arrived in Key West in 1928. A few months later, their first child was born while he was finishing A Farewell to Arms. After spending two winters in Florida, they became permeant residents in this 1851 Spanish colonial mansion until their divorce in 1940. He periodically returned until his death. The house is filled with Papa’s antiques collected during his travels to Europe, Africa and Cuba. The National Historic Landmark is now a museum.

907 Whitehead St, Key West, FL 33040
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7 Sloppy Joe’s Bar in Key West, Florida

Sloppy Joe’s Bar, on the corner of Duval and Greene Streets, looks like another Florida tavern until you learn the history. It was named after a Cuban drinking hole frequented by Ernest Hemingway. Joe Russel opened this version in 1933. He was part of the drinking and fishing crowd called “The Mob.” This is when Hemingway’s nickname became Papa and Joe’s was Habana Joe. Lore has it that Hemingway would stumble home at night using the lighthouse across from his house as his beacon. The original bar is actually a few doors down.

201 Duval St, Key West, FL 33040
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8 Key West Lighthouse in Key West, Florida

The first lighthouse at Key West was erected in 1825 but destroyed during a hurricane in 1846. Two years later, it was replaced by the current light and then extended to a height of 73 feet in 1894. The widow of the first keeper, Barbara Mabrity, maintained the light for 38 years until she was fired at the age of 82 for her outspoken opinions about the Civil War. Members of the Mabrity family worked here for over 85 years! The Key West Lighthouse was decommissioned in 1969 and is now a museum. Walking up its 88 stairs provides a wonderful view of the historic district.

938 Whitehead St, Key West, FL 33040
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9 Holding Out Sculpture by Seward Johnson in Key West, Florida

This matronly woman carrying shopping bags is so realistic I apologized when bumping into her. This life-like sculpture by J. Seward Johnson Jr. is called Holding Out or Waiting to Cross. It is one of several surrounding the Museum of Art and History. Interestingly, the artist dresses his statues of everyday people in real clothes before encasing them in bronze. If you enjoy his work, then plan a visit to the Grounds for Sculpture, his 42-acre sculpture park in Hamilton Township, New Jersey.

281 Front St, Key West, FL 33040
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10 Museum of Art & History in Key West, Florida

This red brick building along Front Street was the Custom House when it was built in 1891. It also served as a post office and district courthouse. The U.S. Navy acquired the property in 1932 but later abandoned it for almost two decades. After a $9 million restoration of this Richardsonian Romanesque landmark, it reopened as the Key West Museum of Art & History.

281 Front St, Key West, FL 33040
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11 Time for Fun Sculpture by Seward Johnson in Key West, Florida

In front of the Museum of Art and History in Key West is this enormous sculpture by Seward Johnson titled, “Time for Fun.” The outdoor art features a couple in Victorian clothes during a romantic slow dance. It was inspired by an 1883 painting by Frenchmen Pierre-Auguste Renoir called “Dance in the Country.” The original models were Paul Lhôte and Aline Charigot. The oil painting hangs in the Musée d’Orsay in Paris.

281 Front St, Key West, FL 33040
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12 Old Coast Guard Headquarters Building in Key West, Florida

Key West remained loyal to the Union during the Civil War. This 1856 building was the barracks for the East Gulf Blockading Squadron. The sailors were responsible for protecting the port from a Confederate invasion that never came. The structure was then used by the Navy until 1932 when it became the headquarters for the Coast Guard. It has now a collection of boutique shops called the Clinton Square Market.

291 Front St, Key West, FL 33040
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13 Harbor House in Key West, Florida

In 1886, at the height of Key West’s Cuban cigar manufacturing, a devastating fire roared through the factories and warehouses plus leveled the surrounding buildings. Soon strict ordinances were put in place for new construction. So The Bank of Key West built their new headquarters using red brick and fashioned a balcony similar to those in New Orleans’ French Quarter. Now called the Harbor House, this retail space on Front Street was ravage by another fire 98 years later.

423 Front St # 2, Key West, FL 33040
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14 Pier House Resort in Key West, Florida

The western shore of Key West is where the Gulf of Mexico meets the Atlantic Ocean. There are many restaurants and hotels positioned to take full advantage of this spectacular view. They are only steps away from Old Town’s attractions. They also provide front row seating to spectacular sunsets. At night, you fall asleep to the lullaby of waves.

1 Duval St, Key West, FL 33040
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15 Western Union Schooner in Key West, Florida

Starting in 1939, the Western Union schooner was used to lay, inspect and repair underwater telegraph cables from Florida to the Caribbean Islands. The vessel’s hull held 20 miles of cable per voyage and is credited with laying more than 30,000 miles of cable until her first retirement in 1974. She then served several purposes, including starring in movies, until finding her home at the Lands End Marina. The boat was listed as a U.S. National Register of Historic Places, was fully restored in 2011 and is considered the flagship of both Key West and Florida. This grand wooden ship is available for tours and short sightseeing cruises.

204 William St, Key West, FL 33040
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16 Historic Seaport Harbor Walk in Key West, Florida

Back in the late 18th century when this island was called Cayo Hueso, ships used this inner harbor when traveling between the Atlantic and the Gulf of Mexico. After John Whitehead was shipwrecked here in 1819, he called it the “Gibraltar of the West.” The harbor was named Port Rodgers once the U.S. took procession of the Keys in 1822. Soon fisheries emerged around the shore of the shallow Key West Bight. This history can be felt along the Historic Seaport Harbor Walk. In addition to a 150 slip marina, it features plenty of restaurants, taverns and shops. If you are looking for water sports, this is also the place to go.

201 William St, Key West, FL 33040
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17 Florida’s Living Reef Mural by Robert Wyland in Key West, Florida

I have always been a huge fan of Robert Wyland’s series of marine murals around the world. So I was excited to experience the “Florida’s Living Reef” in Key West. Number 52 out of 100, this enormous image featuring a stingray, hammerhead shark and coral was created at 201 William Street in 1993 and then repainted in 2012. His partner on this project was Guy Harvey. All of his outdoor art is donated by the Wyland Foundation.

201 William St, Key West, FL 33040
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18 Old Town Trolley Tours Bus in Key West, Florida

Key West is small – only one mile wide and four miles long – and most Old Town attractions are within a compact area. So it is best explored and enjoyed on foot. Other options include guided tours, a hop-on hop off bus such as the Old Town Trolley Tours or renting a bike. There are also plenty of cabs to get you back to your hotel when your shoes begin to pinch.

1 Whitehead St, Key West, FL 33040
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19 President Truman’s Little White House in Key West, Florida

This humble, two-story building was constructed in 1890 on the U.S. Navy base. It served as the home for the commander and briefly housed President William Taft and Thomas Edison early in the 20th century. President Harry S Truman spent his winter vacation here in 1946. He enjoyed it so much he returned ten more times. During those 175 days, it was called the Little White House. Eisenhower and Kennedy also used these accommodations during their presidencies. Plus Jimmy Carter and Bill Clinton stayed here after leaving office. You can feel the history as you walk through the museum on a guided tour.

111 Front St, Key West, FL 33040
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20 Home in Truman Annex Neighborhood in Key West, Florida

While flocking to see the Little White House, most visitors to Key West fail to appreciate the beauty of the nearby homes like this one on Front Street. This gated island community is called the Truman Annex. They were previously residences of officers who served at the 100 acre Naval Station Key West. During the 1990s, they were restored into mansions complete with white picket fences.

112 Front St, Key West, FL 33040
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21 Bishop Albert Kee Statue in Key West, Florida

This bronze statue by Tom Joris is a tribute to Bishop Albert Kee. For decades, he stood along the waterfront selling fish and blowing a conch shell at passing tourists. This tradition dates back to 1830 when arriving Bahamians were called Conchs. In 1982, Key West declared itself the Conch Republic when they claimed to secede from the U.S. If you are born in Key West, you can call yourself a Saltwater Conch. If you are a new resident, it takes seven years before you have the honor of becoming a Freshwater Conch.

Whitehead St & South St, Key West, FL 33040
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22 Southernmost Point Continental U.S.A in Key West, Florida

The most photographed spot in Key West since 1983 is this red, black and yellow striped buoy. It reads, “Southernmost Point in the Continental U.S.A.” Technically, there are a few other locations nearby further south but they are all on private land. So this is close enough to warrant standing in line for your turn at snapping a selfie. The monument also declares Cuba is 90 miles away. It is actually a bit further but that is only important if you are planning to swim there.

Whitehead St & South St, Key West, FL 33040
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23 Southernmost House in Key West, Florida

This gorgeous Queen Anne Victorian mansion at the end of Duval Street was built in 1897 as the residence for Judge Harris and his wife. Thomas Edison designed the home’s electricity. It has also been a speakeasy and a nightclub. Today, the Southernmost House is an inn and museum on the waterfront. It has hosted five presidents and countless famous people. The hotel’s name is derived from being the most southern house in the Continental United States.

1400 Duval St, Key West, FL 33040
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24 Woman Wading at South Beach in Key West, Florida

Key West’s South Beach will never be mistaken for the famous one in Miami Beach. This cube of sand measures only 200 feet and practically disappears at high tide. But it is popular among tourists and locals, just as it was for playwright Tennessee Williams when he visited his Key West home between 1949 and 1983. It is located at the end of Duvall Street next to the South Beach Pier.

1405 Duval St, Key West, FL 33040
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25 Old City Hall in Key West, Florida

The first city hall opened on July 4, 1876. After it burned during the fire of 1886, this red brick replacement was finished in 1892 along Greene Street. The clock tower, which matches the County Courthouse, was finished on the bicentennial in 1976. The property was restored by the Historic Florida Keys Preservation Board.

510 Greene St, Key West, FL 33040
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26 Smiling Pig with Cigar Mural in Key West, Florida

This smiling pig sporting sunglasses and smoking a cigar is the logo for Charlie Mac’s, a restaurant on Southard Street in Key West. The wonderful aroma of smoked pork draws you in and the delicious barbeque sauce will linger in your memory for days. If you eat at an outdoor table, you will be accompanied by wild roosters in search of a handout. I am not sure if they are featured as their chicken wings. The eater is owned by former Philadelphia 76ers president Pat Croce.

404 Southard St, Key West, FL 33040
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27 Former First National Bank Building in Key West, Florida

In 1891, George Allen started the First National Bank of Key West with capital from owners of cigar manufacturers. The financial institution constructed this red and yellow brick building on Duval and Front Streets in 1897. In later years it was a Wachovia branch before the holding company failed and was acquired by Wells Fargo. Now the lower level of this historic building is a clothing store.

420 Front St, Key West, FL 33040
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Vintage Camper Trailer Painted with Landmarks in Key West, Florida

There is no question where home is for this vintage camper trailer. It is painted with images surrounding Key West. American’s love affair with campers took off after World War II when baby boomer families discovered the joy of road trips. Conversion vans arrived in the 1960s, the Airstream became popular a decade later and by the 1990s the RVs had become enormous.

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28 Crucifixion Stained Glass Window in Key West, Florida

Crucifixion Stained Glass Window in Key West, Florida
One of the four founders of Key West died in 1832. The widow of John William Charles Fleming then donated his land to the newly formed Episcopal church. Their first building was finished in 1839, destroyed by a hurricane seven years later and rebuilt in 1848. St. Peter’s parish was founded here in 1875. The church was destroyed two more times. Today’s version of St. Paul’s Episcopal Church on Duval Street dates back to 1919. Inside are lovely stain-glass windows of Biblical scenes like this one of the Crucifixion.

401 Duval St, Key West, FL 33040
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29 Captain Martin Hellings House in Key West, Florida

This Victorian mansion was built on Duval Street for Martin Hellings in 1892. The construction was financed by his wife’s father and Florida’s first millionaire, William Curry. Hellings was a Union captain during the Civil War and provided the White House with intelligence about Cuba during the Spanish American War. The Key West Woman’s Club bought the former residence in 1940 to serve as Key West’s first public library.

319 Duval St, Key West, FL 33040
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30 Basilica of St. Mary Star of the Sea in Key West, Florida

When St. Mary Star of the Sea was founded in Key West in the mid-19th century, it was the third attempt by Catholics to establish a parish on the island. It is dedicated to Our Lady, Stella Maris. The word “Sea” does not mean the oceans. Instead, it refers to the Virgin Mary as a guiding light. The first church was built in 1852, destroyed in 1901 and replaced with the current Victorian structure in 1905. The minor basilica is listed on the National Register of Historic Places.

1010 Windsor Ln, Key West, FL 33040
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31 Cherub Monument at Key West Cemetery in Key West, Florida

A walk through the Key West Cemetery is a walk through the city’s history. Located in Old Town on Solares Hill, it was founded in 1847 after a hurricane destroyed the previous graveyard. Sections are devoted to different religions and nationalities. One area is a memorial to 260 sailors who died on the U.S.S. Maine in 1898. Some of the graves are simple and overgrown while others display elaborate markers and monuments. Most of the crypts are built above ground. The cherub typically connotes the death of a child. Guided tours are available so you can learn about the famous former citizens.

701 Pauline St, Key West, FL 33040
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32 The Lobster Shack Restaurant in Key West, Florida

If you are hungry after your very long drive along U.S. Route 1 from northern Maine to Key West, then The Lobster Shack will serve you a home-cooked meal of clam chowder and lobster rolls with a grilled cheese sandwich stuffed with more lobster. Your stomach will feel like it never left New England. This is one of several small restaurants in Key West where your meal is served in a historic home.

507 South St, Key West, FL 33040
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33 Boardwalk to Smathers Beach in Key West, Florida

Key West’s most popular beach is Smathers. Located on the southern shore facing the Atlantic Ocean, it stretches for a half mile and runs parallel to South Roosevelt Boulevard. If you arrive early, you can find a place to park along the sidewalk. Wooden boardwalks are evenly spaced for easy access to the beach.

2601 S Roosevelt Blvd, Key West, FL 33040
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34 Calm Waters at Smathers Beach in Key West, Florida

East coast beaches along the Atlantic Ocean typically experience lots of waves. Just the opposite is true at Smathers Beach. The surrounding coral reef acts as a natural barrier against the surf. Plus there are three rock breakwaters spaced across the half mile of sand. The delightful result is calm, warm water. This combination is perfect for swimming and playing, even for small children.

2601 S Roosevelt Blvd, Key West, FL 33040
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35 Water Toys Available at Smathers Beach in Key West, Florida

If you don’t want to sit in the sun all day, then you will find plenty of water toys to rent at Smathers Beach. Your options include Hobie Cats, jet skis, kayaks, windsurfers, Sun Fish sailboats, wave runners and paddle boards. Reef snorkel tours are also available. If this long list makes you tired, then maybe you prefer renting an umbrella over a beach chair in order to enjoy a nap.

2001 S Roosevelt Blvd, Key West, FL 33040
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36 White Sand along Smathers Beach in Key West, Florida

If you have visited beaches along the Florida Keys, you were probably disappointed. Many of the shorelines are rocky and rough … not ideal for going barefoot. So, your toes will really love the pure white sand at Smathers Beach. Yes, it is man-made. Do you care?

2001 S Roosevelt Blvd, Key West, FL 33040
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37 Beach Volleyball Game at Smathers Beach in Key West, Florida

Since it began on Waikiki Beach in 1915, beach volleyball has become almost as common as sand and surf along a tropical shoreline. It has grown into a professional sport and in 1996 it became part of the Olympics. There always seems to be an afternoon game or two at Smathers Beach. If you are no longer a high school or college student, it is fun to watch the competition.

1900 S Roosevelt Blvd, Key West, FL 33040
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38 Food Truck along Smathers Beach in Key West, Florida

If you get hungry while enjoying Smathers Beach, then look for the Beach Bites food truck parked curbside along South Roosevelt Boulevard. Their Mexican and Cuban specialties include tacos, wraps, burritos and quesadillas.

1900 S Roosevelt Blvd, Key West, FL 33040
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39 Bicyclists Riding on White Street Pier in Key West, Florida

The White Street Pier extends about a quarter mile into the Atlantic along Key West’s southern shore next to Higgs Beach. The locals call it the “Unfinished Highway to Havana.” The concrete promenade is a favorite among cyclists, strolling tourists and ocean lovers who are eager to warm a park bench. The pier marks the beginning of the Key West Marine Park yet fishing from the pier is allowed. Fresh catches include snappers and groupers.

White St, Key West, FL 33040
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40 Gazebo at West Martlello Tower in Key West, Florida

This red brick wall a few steps from the White Street Pier was planned to be a casemate battery with cannons pointing towards the Atlantic Ocean. Construction of the West Martello fort and towers began during the Civil War in 1863. The U.S. Army stopped the unfinished citadel ten years later. It housed troops during the Spanish American War (late 19th century) and during World War I and II. The National Historic Site is now managed by the Key West Garden Club. Admission is free but a donation is always appreciated.

1100 Atlantic Blvd, Key West, FL 33040
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41 Banyan Tree at West Martlello Tower in Key West, Florida

It is easy to see how these twisted banyan branches earned this tree the nickname “Florida strangler fig.” This native can reach a height of 100 feet while forming an enormous canopy. This ficus aurea is one of several gorgeous plants and flowers you will enjoy while walking along the outdoor paths at West Martlello Tower. They are maintained by the Key West Garden Club.

1100 Atlantic Blvd, Key West, FL 33040
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42 Sunning at Higgs Beach in Key West, Florida

Between the White Street Pier and the Reynolds Street Pier in the background is the Clarence S. Higgs Memorial Beach. The 16.5 acres includes ramp-accessible pavilions, fast-food restaurant, dog-friendly park, playground for kids, courts for tennis and volleyball plus places to rent water toys and chairs for a delightful day in the Florida sun. Parking and the sand are included at no charge.

1000 Atlantic Blvd, Key West, FL 33040
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43 Casa Marina Resort in Key West, Florida

Henry Flagler was the founder of Standard Oil and a major developer in – some say the father of – Saint Augustine, Miami and Palm Beach. Part of his vision for creating an American Riviera was building a railroad along Florida’s east coast. In 1905, he committed to extending rails to Key West. The Florida Overseas Railroad was finished in 1912. He also wanted a premiere hotel where his arriving passengers could stay in luxury. He died in 1913, seven years before his dream of the Casa Marina Resort was realized. Today this historic hotel is a Waldorf Astoria Resort.

1500 Reynolds St, Key West, FL 33040
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44 Casa Marina Resort Private Beach in Key West, Florida

Florida law stipulates all coastlines are public but there are several beaches in Key West cordoned off by hotels. The longest private beach stretches 1,100 feet in front of the Casa Marina Resort. This Atlantic shoreline and adjoining 6.5 acres of property were purchased for $1,000 before construction of the luxury hotel began in 1914. In the background is the pier of a sister hotel, The Waldorf Astoria Beach Resort.

1500 Reynolds St, Key West, FL 33040
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45 The Reach Hotel Gazebo and Pier in Key West, Florida

The Reach, a Waldorf Astoria Resort, owns this gazebo and pier. It extends out into the Atlantic and the middle of the Key West Marine Park. The state, city and Casa Marina Resort teamed up to create this motor-free zone extending 600 feet from shore. The buoyed area protects the coral reef and marine life plus the snorkelers who enjoy it. The Florida Reef is the only one in the Continental U.S. and the world’s third largest.

1435 Simonton St, Key West, FL 33040
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46 Swaying Palm Trees at the Beach in Key West, Florida

Almost any photo of swaying palm trees makes you think of the tropics. That is because they grow best in sandy conditions despite the ocean’s salinity. Key West’s climate is also perfect for coconut trees. The average temperature is 78° Fahrenheit with only about 100 cloudy days a year. You will also enjoy seeing royal palm trees on the island.

2601 S Roosevelt Blvd, Key West, FL 33040
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