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Every night in Key West, hundreds of strangers gather to clap at the sun

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People take pictures of the famous sunset at Mallory Square, Key West

It’s Been Going Strong for Decades

Every evening, hundreds of people line the waterfront at Mallory Square in Key West’s Old Town, facing the Gulf of Mexico, waiting for the same thing. The sun goes down, and the crowd claps.

That tradition reportedly started with Tennessee Williams, and it hasn’t stopped since.

The Sunset Celebration runs 365 days a year, with food vendors, artisan stalls, and live entertainment rolling in about two hours before the show.

Mallory Square sits at the northern end of Duval Street, and from here, the rest of Old Town fans out in every direction. But nobody leaves early.

Key West, Florida, USA - September 12, 2019: people enjoy the sunset point at Mallory square in Key West, USA. This place is the most popular sunset point in Key West

Wreckers and steamships built this waterfront

Mallory Square has anchored Key West’s social life since the early 1820s, when master wrecker Asa Tift docked ships loaded with salvaged cargo right here.

The square gets its name from the Mallory Steamship Company, founded by Charles H. Mallory of Mystic, Conn., which launched passenger and freight service to the island in 1873. By 1961, the aging waterfront needed help.

The City of Key West and the Old Island Restoration Foundation turned decaying docks into the public gathering place you walk through today.

The Sunset Celebration caught on in the late 1960s and got its formal structure in 1984.

Key West, Florida, United States - April 13, 2012: a tightrope walker tosses of skittles. Show of street artists that takes place every day during the sunset celebration at Mallory Square in Key West.

Sword swallowers and fire dancers own the sunset

When the Sunset Celebration kicks in, Mallory Square turns into an open-air stage. Sword swallowers, fire dancers, jugglers, tightrope walkers, and trained animal acts spread across the plaza.

Conga drummers set up on one side. Solo guitarists play on the other.

You walk a few steps and the soundtrack changes completely. Psychics read palms while caricature artists sketch tourists.

Local artists sell handmade jewelry and paintings, and food vendors push conch fritters and tropical treats.

A city ordinance forces cruise ships to leave port at least two hours before sunset, so nothing blocks your view of the horizon.

Key West Florida Keys Florida USA - May 15 2017 : Key West Aquarium Florida one of Florida's oldest aquariums

The aquarium opened in 1935 and survived a war

At 1 Whitehead Street, right on the square, you’ll find the Key West Aquarium. It opened on Feb. 17, 1935, as the first open-air aquarium in the country.

Dr. Robert Van Deusen of Philadelphia’s Fairmount Park Aquarium came up with the idea, and the Civil Works Administration funded it during the Great Depression.

Today it holds more than 250 specimens, including sharks, tropical fish, and four of the five sea turtle species found in the Florida Keys. You can handle conchs, sea stars, and horseshoe crabs at the touch tank.

During World War II, the military converted the building into a rifle range before the city reclaimed it in 1946.

Key West Jan 2019, Museum of Art and History at the Custom House, a monumental civic building from 1891, restored as a museum for the Key West Art Historical Society. near Mallory Square

A red-brick customs house towers over the harbor

The Key West Museum of Art and History sits inside an 1891 Richardsonian Romanesque building that dominates the skyline above Mallory Square.

It started life as the island’s customs office, post office, and federal courthouse.

By 1882, Key West’s customs operations pulled in more annual revenue than every other Florida port combined, fueled by the wrecking and cigar industries. The Navy left the building in the 1970s, and it fell apart.

A $9 million restoration brought it back, and the museum reopened in 1999.

Inside, you’ll find Guy Harvey’s 59 pen-and-ink illustrations of Hemingway’s “The Old Man and the Sea” and 15 rarely seen paintings by Tennessee Williams.

Key West, Florida

$450 million in treasure from the ocean floor

Steps from Mallory Square at 200 Greene Street, the Mel Fisher Maritime Museum holds nearly 100,000 artifacts pulled from 17th-century shipwrecks.

Mel Fisher spent 17 years hunting the Spanish galleon Nuestra Senora de Atocha, which went down in a 1622 hurricane as part of a 28-ship fleet off the Florida Keys.

On July 20, 1985, his crew brought up roughly $450 million in gold, silver, and emeralds. The collection includes a 77.76-carat uncut emerald crystal, gold coins, silver bars, and bronze cannons.

A separate exhibit tells the story of the Henrietta Marie, an English slave ship that sank near Key West in 1700.

Key West, Florida, USA - September 1, 2018: Sunrise over the Shipwreck Museum in Key West, Florida. For editorial use.

Wreckers made Key West the richest city in America

The Key West Shipwreck Treasures Museum on Mallory Square digs into the industry that once gave Key West the highest per capita wealth in the country.

In the 1800s, treacherous reefs around the Florida Keys sent hundreds of ships to the bottom, and local wreckers built fortunes pulling cargo from the water.

You can see artifacts from notable wrecks, including the Isaac Allerton, and watch video presentations on the dangerous work.

Wreckers watched from lookout towers for ships in trouble, then raced each other to reach them first. Climb the museum’s 65-foot observation tower for a wide view of Key West and the surrounding waters.

Waterfront Playhouse

Florida’s oldest theater group lives in an ice warehouse

The Waterfront Playhouse on Mallory Square is home to the Key West Players, believed to be the oldest continuously running theater group in Florida.

The group started in 1940, bounced around Key West for two decades, and landed a permanent home on the square in 1961.

Tennessee Williams, who lived in Key West for years, helped them secure a renovated 1880s ice warehouse on the waterfront.

The intimate 150-seat theater runs comedies, dramas, musicals, and world premieres from roughly November through June. Florida Monthly Magazine has named it the best professional theater in the state.

KEY WEST, FLORIDA/USA - NOVEMBER 12, 2019: The Key West Memorial Sculpture Garden, with 26 busts of notable Key West residents created by master sculpture James Mastin.

39 bronze faces stare back from the shoreline

The Key West Historic Memorial Sculpture Garden opened in Sept. 1997 on the original shoreline of Mallory Square, right in front of the Waterfront Playhouse.

Sculptor James Mastin created all 36 original bronze busts, now expanded to 39, honoring the men and women who shaped Key West’s history. You’ll recognize Ernest Hemingway, Harry S. Truman, and Henry Flagler among them.

A 20-foot monument called “The Wreckers” shows early salvagers hauling cargo from the sea.

The garden draws more than a million visitors a year and includes a brick walkway where donors can have their names engraved.

Key West, Florida, USA - 22nd January 2026: Island Time: The Iconic Street Clock and Historic Art Deco Architecture of Duval Street, Key West

The square’s oldest building survived the Great Fire

The Key West Art Center sits inside a frame structure originally built in 1853 as a grocery store. It survived the Great Fire of 1886, got rebuilt, and became Key West’s first public art gallery in 1935.

The Art Center moved in during 1960 and still operates as an open gallery today.

Nearby, two octagonal concrete cable huts built in 1921 and 1932 once stored communications cable connecting Key West to Cuba and South America.

These small, restored structures pack layers of history into a few hundred feet of waterfront.

Key West, Florida, United States - November 1, 2018: Sculpture of people at the Key West Museum of Art u0026 History.

Three-story sculptures rotate outside the Custom House

Monumental sculptures by artist Seward Johnson stand on the grounds outside the Custom House, with some pieces reaching three stories tall.

Past installations have included towering takes on famous paintings and photographs, turning the museum grounds into an outdoor gallery you can walk through for free.

Smaller, life-sized bronze figures of everyday people sit scattered around the square, blending into the streetscape so well you might walk past one before you realize it’s not real.

The displays change with the seasons, so if you’ve been before, something new is probably waiting.

Key West, FL, USA - February 18, 2023: tourists enjoying sunset time in Mallory Square, a famous tourist place in the city.

The party runs from morning coffee to the last clap

During the day, Mallory Square slows down. You can walk the waterfront, duck into museums, and browse the open-air market without fighting the evening crowds.

Vendors sell handmade souvenirs, natural sea sponges, and seashell crafts tied to Key West’s maritime roots. Food ranges from fresh seafood and Cuban fare to tropical fruit smoothies and the island’s famous key lime pie.

The Conch Tour Train, running since 1958, departs from the area and loops through Key West’s top landmarks.

As afternoon fades, the energy picks up, and the square shifts back into the festival that has pulled people in for more than half a century.

Tourists visit Mallory Square Key West Florida FL destination for Western Caribbean Cruise from Tampa. created 03.25.23

Visit Mallory Square in Key West, Florida

You can walk to Mallory Square from most spots in Old Town Key West. It sits at 400 Wall Street, and the square stays open 24 hours a day, seven days a week.

The Sunset Celebration starts about two hours before sunset every evening, year-round. Paid parking is available at the Mallory Square city lot, but there’s no free parking downtown.

The Old Town Trolley and Conch Tour Train both stop nearby.

Key West is about a three-and-a-half-hour drive from Miami on the Overseas Highway, or you can fly into Key West International Airport.

This article was created with AI assistance and human editing.

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Currently residing in the "Sunset State" with his wife and 8 pound Pomeranian. Leo is a lover of all things travel related outside and inside the United States. Leo has been to every continent and continues to push to reach his goals of visiting every country someday. Learn more about Leo on Muck Rack.

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