The Perfect Day in Key West

Begin your perfect day in Key West exploring this compact town by foot, bike, or hop-on-hop-off trolley. Stop in at the Ernest Hemingway house, enjoy a casual seafood lunch, browse the boutiques and art galleries on Duval Street, take a selfie in front of the Southernmost Point in the U.S., then get down to Mallory Square for the sunset celebration.

New Orleans may be home to America’s most festive thoroughfare, Bourbon Street, but Key West’s Duval Street is a close second. This two-kilometer-long (1.25-mile-long) road runs from north to south, from one end of the island to the other, and passes through the city’s historic Old Town. It’s lined with bars, restaurants, stores and galleries—many of which are among Key West’s most famous, including Sloppy Joe’s, a Hemingway hangout back in the 1930s and still a hotspot today. By day it’s mostly for shoppers, but it really heats up at night, with huge crowds strolling up and down the street, live music spilling out from the bars and a party atmosphere all around.

Whitehead St & South Street, Key West, FL 33040, USA
The Southernmost Point buoy, at the corner of Whitehead Street and South Street, marks not only the spot for the southernmost point of the continental United States but also the distance (90 miles) to the next country, Cuba. The buoy, installed by the city in 1983, is visited by thousands of people each day. (Before the buoy, a small sign stood at the spot alongside a line of seashells for purchase.) Taking a photo in front of the buoy is imperative for a first visit to Key West, so bring a tripod, or ask a stranger to snap a few shots. Buskers play music, and street vendors sell food and goofy souvenirs and slash open coconuts to drink.
6810 Front St, Stock Island, FL 33040, USA
Hogfish Bar and Grill, under a thatched palapa roof with open sides, is tucked in among the boats and gulls of Safe Harbour Marina in Stock Island. In short, a meal or a drink there makes you feel like an insider, a salty local far from the crowds downtown. That in-crowd feeling is burnished on weekends, when local bands play sets, or during one of the events held by Hogfish during the season, like shrimp boils. The simple food is served generously on plates crowded with side dishes. The hogfish sandwich, served fried on Cuban bread, is the stuff of late-night-post-beer legend.

1 Whitehead St, Key West, FL 33040, USA
In the center of Mallory Square you can visit the Sponge Market Shop, which doubles as a museum that depicts the history of the sponging industry in Key West. In the early 19th century the Key West fishermen found sponges washed up on the beaches after storms. This discovery led to the sponging business in Key West. The sponges were collected from the shallow waters near the shore with a pronged rake. The sponges were then sorted and dried for the local market. Until 1849, these sponges were used and sold locally. That year spongers sent a sample of Key West’s fine sponges to New York. By the late 19th century the New York market was huge, and Key West held a great monopoly of the sponge trade in the U.S. At one point, there were as many as 250 boats in the Key West sponge fleet. More then 1400 people were employed in the sponge trade. Around 1905, the Key West sponge beds were fairly depleted and the trade was taken over by the Tarpon Springs, Florida spongers. The Key West Sponge Market Shop carries many different sizes and colors of sponges, for great prices. There are also many other souvenirs available. I dawdled in this museum/shop for about an hour, as I was very interested in the pictures and history of this fascinating industry. The sponges I bought as gifts were very appreciated. If you like history and high quality goods, this is the place for you.
400 Wall St, Key West, FL 33040, USA
Key West is billed as “the Home of the Sunset,” which means every time the sun sinks below the horizon, it’s time for a party. Since the 1960s, Mallory Square’s dock has been hosting this nightly celebration, which begins two hours ahead of sunset with jugglers, musicians, artists, and street performers showing off their talents while food carts serve up conch fritters and Key lime pie. Soak up the quirky scene while waiting for the big show in the sky.

729 Thomas St, Key West, FL 33040, USA
Blue Heaven is a favorite in Key West—Jimmy Buffett even mentioned it in one of his famous beach tunes. The whimsical courtyard is filled with brightly colored tables and chairs, twinkly lights, foliage, and stray animals. The bar and restaurant is owned and operated by a husband and wife whose creative backgrounds in art and literature inspired the space. There’s a mini art gallery, a sandwich shop, and roaming roosters on the grounds. Once a boxing ring (with Ernest Hemingway as referee), the spot now pays tribute to the Caribbean, with bright accents and Cajun seasonings on the menu. Menu highlights include the scallops, which are locally celebrated, served with white wine and lemon butter with tomatoes, onions, mushrooms, and lots of garlic. Locals say the Key lime pie is one of the best in town.
601 Whitehead St, Key West, FL 33040, USA
Chances are that when you return home after your trip to Key West, someone will ask you if you went to the Green Parrot. It’s that kind of iconic bar, the kind your parents’ friends ended up at over spring break in college long ago. The bar started as a local grocery store about a hundred years ago; the building became the Brown Derby, a bar that was popular first with the submarine sailors from the naval base down the street.

When the naval base closed in the ‘70s, the bar transitioned into a hangout for fishermen and local sailors and the hippies that began to drift into town. The Green Parrot still has the air of a honky-tonk, lit exclusively by spotlight and neon, with a roster of almost-nightly live music, mostly of the bluesy, rollicking sort.
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