The only street in America that touches two oceans is 1.25 miles long in Key West

Duval Street’s 1.25-mile stretch

You can walk from the Gulf of Mexico to the Atlantic Ocean in about 30 minutes, and you never leave the same street.

Duval Street cuts 1.25 miles through Key West’s Old Town, the only street in the country that connects two bodies of water.

That earned it the nickname “The Longest Street in the World,” not for distance but because it spans the full width of the island. In 2012, the American Planning Association named it one of America’s “Great Streets.”

The colorful buildings, galleries and landmarks along the way make a full day easy to fill, and that’s before you even get to the sunset.

A dirt road with a tidal pond down the middle

Before it was a landmark, Duval Street was a dirt path with a tidal pond running through the center of it, serving a small community of sailors and shipwreck salvagers.

The street carries the name of William Pope Duval, Florida’s first civilian territorial governor from 1822 to 1834.

Cuban immigrants started arriving in the late 1860s and brought cigar manufacturing with them, earning Key West the title “Cigar City USA.”

The Bahamian and Spanish-influenced Victorian mansions you see today survived thanks to preservation efforts dating back to the 1960s.

A 1967 National Park Service survey flagged 18 buildings as historic landmarks, and by 1971, six full blocks had landed on the National Register of Historic Places.

Applauding the sunset at Mallory Square

Mallory Square sits at the northern tip of Duval Street, right on the Gulf of Mexico.

About two hours before sunset every evening, the square turns into an open-air arts festival run by the Key West Cultural Preservation Society, a nonprofit that has managed the event since 1984.

Jugglers, tightrope walkers, magicians and trained animal acts spread across the plaza while artisans sell handmade crafts and jewelry.

Hundreds of people gather each night, and when the sun drops into the Gulf, the crowd claps. That tradition goes back decades, and it happens 365 days a year.

The open-air aquarium built during the Depression

The Key West Aquarium at 1 Whitehead Street, right next to Mallory Square, is the oldest attraction on the island.

The federal government built it between 1932 and 1934 as a Depression-era works project, and it opened on Feb. 17, 1935, as the first open-air aquarium in the country.

During World War II, the military leased the building and used it as a firing range before it went back to holding fish.

Today it houses more than 250 specimens, including sharks, sea turtles, tropical fish and stingrays. The touch tank lets you handle sea stars, horseshoe crabs, hermit crabs and sea cucumbers.

Where Cuba’s independence movement took root

At 516 Duval Street, the San Carlos Institute has stood as a Cuban heritage center since 1871, when exiles fleeing Cuba’s Ten Years’ War founded it in Key West.

In January 1892, Cuban revolutionary and poet Jose Marti spoke here, uniting the exile community and establishing the Cuban Revolutionary Party.

The institute ran one of the first bilingual, racially integrated schools in the country, teaching children of all backgrounds in English and Spanish for more than a century.

When the facade collapsed in 1981, the community raised the money to restore it.

The San Carlos reopened on Jan. 3, 1992, exactly 100 years after Marti’s speech, and now operates as a museum, theater, gallery, library and cultural center.

Flamingos and 60 species of butterflies under glass

Near the southern end of Duval at 1316, the Key West Butterfly and Nature Conservatory keeps 50 to 60 butterfly species from around the world inside a climate-controlled glass dome.

More than 20 species of exotic birds share the space, including a pair of American flamingos.

You walk through cascading waterfalls, flowering tropical plants and thick greenery while butterflies land on your shoulders.

A learning center screens a 15-minute film on butterfly life cycles and has a nursery where you can watch caterpillars develop in chrysalis.

The conservatory has been voted Key West’s top family-friendly attraction multiple years running.

They poured the buoy in concrete so nobody could steal it

The Southernmost Point Buoy stands 12 feet tall and seven feet wide, a painted concrete marker dedicated on Sept. 10, 1983.

It marks the southernmost point you can reach in the continental United States and reads “90 Miles to Cuba.”

The city used to have a wooden sign at the spot, but people kept stealing it, so they poured a concrete buoy too heavy for anyone to haul off.

As of September 2025, the original buoy at South and Whitehead Streets is closed for seawall and plaza repairs.

A full-scale replica now sits at Duval Pocket Park at 1400 Duval Street until the original location reopens in late 2026.

Hemingway’s bar opened the day Prohibition ended

Sloppy Joe’s sits at the corner of Duval and Greene Streets, and it opened on Dec. 5, 1933, the exact day Prohibition ended.

Local entrepreneur Joe Russell founded the place, and Ernest Hemingway became a regular during his years in Key West from 1928 to 1938.

The two were close friends, and Russell inspired the character Freddy in Hemingway’s novel “To Have and Have Not.”

A 1933 mural by artist Erik Smith showing Russell, Hemingway and legendary bartender “Big Skinner” still hangs on the wall.

Sloppy Joe’s landed on the National Register of Historic Places in 2006, and every July, dozens of bearded contestants show up for the Hemingway Look-Alike Contest.

Cuban cigars rolled on-site and a Walgreens inside a movie palace

Art galleries line Duval Street with island-inspired paintings, tropical wildlife pieces and work by local artists. Shops sell handmade jewelry, colorful sundresses and one-of-a-kind Key West memorabilia.

You can step into cigar shops where rollers twist fresh Cuban-style cigars by hand, carrying on a tradition from the manufacturing boom of the mid-1800s.

One of the street’s stranger sights is a Walgreens inside the old Strand Theater, a former movie palace that once seated more than 800 people. The ornate facade and decorative exterior are still intact.

Many of the shops sit inside restored 19th-century buildings with wide porches and shuttered windows.

The week Key West seceded from the United States

Every April, the Conch Republic Independence Celebration marks Key West’s famous 1982 tongue-in-cheek secession from the United States, a protest stunt against a U.S. Border Patrol checkpoint that was choking off tourism.

That joke turned into lasting local pride and now fills multiple days with food, music and offbeat events. Hemingway Days in July brings the Look-Alike Contest, a Caribbean street fair and literary readings.

Key West Lobsterfest in August kicks off lobster season with four days of free concerts, arts and fresh crustacean.

The Key Lime Festival in late June and early July celebrates the island’s signature citrus with tastings and pie contests. Duval Street serves as the main stage and parade route for nearly all of them.

Sixteen years of searching for Spanish shipwreck gold

Steps from Duval Street near Mallory Square, the Mel Fisher Maritime Museum holds treasures pulled from 17th-century Spanish shipwrecks.

Treasure hunter Mel Fisher spent 16 years searching before he hit the mother lode of the Nuestra Senora de Atocha in 1985, pulling up silver bars, gold, emeralds and thousands of artifacts.

The museum is the only fully accredited museum in the Florida Keys and displays original pieces from the Atocha and the Santa Margarita alongside exhibits on maritime archaeology.

You can explore interactive displays on shipwreck salvaging, the industry that once made Key West one of the wealthiest cities per capita in the country.

The museum also covers the history of the slave trade and artifacts from the Middle Passage.

Roosters in the crosswalk and a two-by-four-mile island

Free-roaming roosters and chickens cross Duval Street whenever they feel like it, protected by local ordinance and treated as part of the scenery.

Key West residents call themselves “Conchs,” a name borrowed from the Bahamian settlers who arrived in the 1800s.

That identity took on new life after the 1982 mock secession, when the Keys declared independence to protest the Border Patrol checkpoint disrupting tourism.

The whole island measures two miles by four miles, and bikes and walking are how most people get around.

Duval Street’s mix of preserved architecture, living history and open sky makes it unlike any other main street in the country.

Walk Duval Street in Key West, Florida

You can pick up Duval Street at Mallory Square on the Gulf side and walk the full 1.25 miles south to the Atlantic. The Mallory Square Sunset Celebration starts about two hours before sunset every evening, year-round.

The Key West Butterfly and Nature Conservatory at 1316 Duval Street is open daily from 9 a.m. to 5 p.m. The Southernmost Point Buoy replica sits at Duval Pocket Park, 1400 Duval Street, through late 2026 during plaza repairs.

Many spots along the street shift to adults-only after about 9 p.m., so check with individual venues. Key West is about 160 miles south of Miami via the Overseas Highway on U.S. Route 1.

This article was created with AI assistance and human editing.

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