Things to do in Sugarloaf Key
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Top places to visit
1. Duval Street
Coming to Florida’s Key West and not experiencing Duval Street is missing one of the area’s most important commercial roads. It’s the main street on the island. Visit at any time. At the end of the day, when the heat abates and beachgoers have packed up, the street truly comes into its own. Being bored on Duval Street is a rarity.
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2. Southernmost Point
Visit the Southernmost Point of the United States for a unique photo opportunity and views toward Cuba. Pose in front of the huge structure emblazoned with the words, “Southernmost Point Continental U.S.A.” and “90 miles to Cuba,” for a memorable photograph.
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3. Mallory Square
This popular town square, adjacent to excellent dining and lively bars is home to one of Key West’s longest-running traditions. Perched on the edge of the Gulf of Mexico, Mallory Square hosts Key West’s Sunset Celebration every evening of the year. Watch as the square bursts with color and sound as hundreds of visitors to the island converge to watch one of the most picturesque sunsets in the United States. Surrounding the square are some of Key West’s best restaurants, great shopping and hotels catering to all budgets.
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4. Smathers Beach
On an island filled with private beaches, this popular stretch of public shoreline is among the most majestic. Featuring over a half-mile (0.8 kilometer) of white, palm-lined sand, Smathers Beach is a destination for water sports lovers and those seeking quiet time in the sun. Spend a day snorkeling, kayaking or playing beach volleyball as you make friends on the beach known for its social atmosphere.
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5. South Beach
Conveniently located at the end of one of Key West’s main streets and just a short walk from the center of the town, this tiny beach is the most popular on the island. While its warm water, perfect swimming conditions and stunning views attract many visitors, some visit South Beach simply to say they’ve been to the southernmost beach in the continental United States. Find a spot on the crowded beach to immerse yourself in the lively Key West atmosphere or simply stop by for a quick swim on your way into town.
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6. Ernest Hemingway Home and Museum
Visit the Ernest Hemingway Home and Museum to reveal the eccentricities of Ernest Hemingway’s life. For most of the 1930s, one of the most revered authors of the 20th century lived in a Spanish colonial house in the heart of tropical Key West. Meet six-toed cats and see the studio in which some of Hemingway’s most famous novels were written. Find a vast collection of art, hunting trophies and household items as you wander through the house and gardens.
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What to do in Sugarloaf Key
Popular places to visit

Upper Sugarloaf Sound
Commune with nature and explore the great outdoors at Upper Sugarloaf Sound during your travels in Summerland Key.
Sugarloaf Beach
Why not spend a lazy afternoon at Sugarloaf Beach during your trip to Summerland Key?
Upper Sugarloaf Key
Commune with nature and explore the great outdoors at Upper Sugarloaf Key during your travels in Summerland Key.
Areas of Sugarloaf Key

Sugarloaf Shores
Though Sugarloaf Shores may not have many top sights, you can venture to the surrounding area to see attractions like Florida Keys Beaches and Sugarloaf Beach.
- Duval Street
- Mallory Square
- Smathers Beach
- Ernest Hemingway Home and Museum
- Fort Zachary Taylor Historic State Park
- Boca Chica Nude Beach
- Harry S. Truman Little White House
- Key West Butterfly and Nature Conservatory
- Key West Lighthouse and Keeper's Quarters Museum
- Simonton Beach
- Robbie's
- Fort East Martello Museum and Gallery
- Hotels near Duval Street
- Hotels near Mallory Square
- Hotels near Smathers Beach
- Hotels near Ernest Hemingway Home and Museum
- Hotels near Key West Golf Club
- Hotels near Clarence S. Higgs Memorial Beach Park
- Hotels near Key West Butterfly and Nature Conservatory
- Hotels near Key West Shipwreck Museum
- Hotels near Robbie's
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