Things to do in Sugarloaf Key
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Sugarloaf Key must see attractions
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. 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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3. 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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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. Fort Zachary Taylor Historic State Park
Fort Zachary Taylor Historic State Park is a sublime natural setting that provides idyllic swimming and birdwatching conditions. At its core is the historic Fort Taylor and what is thought to be the world’s largest Civil War arms collection. Bring U.S. history to life by walking down the passageways of this well-preserved fortress.
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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
Discover the most popular places to visit in Sugarloaf Key

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

Sugarloaf Shores
While Sugarloaf Shores isn't home to many top sights, Upper Sugarloaf Sound and Florida Keys Beaches are some notable places to visit nearby.
Frequently asked questions
- Places to visit
- Hotels near popular Summerland Key Attractions
- Nearby cities for things to do
- Expedia's Latest Trends
- Duval Street
- Mallory Square
- Southernmost Point
- Smathers Beach
- Fort Zachary Taylor Historic State Park
- Ernest Hemingway Home and Museum
- South Beach
- Key West Butterfly and Nature Conservatory
- Clarence S. Higgs Memorial Beach Park
- Boca Chica Nude Beach
- Harry S. Truman Little White House
- Key West Lighthouse and Keeper's Quarters Museum
- Florida Keys National Marine Sanctuary
- Audubon House and Tropical Gardens
- Key West Shipwreck Museum
- Key West Visitors Center
- Robbie's
- Fort East Martello Museum and Gallery
- Hotels near South Beach
- Hotels near Florida Keys Beaches
- Hotels near Duval Street
- Hotels near Southernmost Point
- Hotels near Smathers Beach
- Hotels near Fort Zachary Taylor Historic State Park
- Hotels near Ernest Hemingway Home and Museum
- Hotels near Harry S. Truman Little White House
- Hotels near Florida Keys National Marine Sanctuary
- Hotels near Calusa Beach
- Hotels near Florida Keys Eco - Discovery Center
- Hotels near Key West Historic Seaport
- Hotels near Key West Naval Station
Expedia's Latest Trends
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