Title: 10 TOP Things to Do in Sugarloaf Key September 2025 | Expedia.ca [Sugarloaf Key Travel Guide](https://expedia.ca/Sugarloaf-Key.dx183126)[Hotels in Sugarloaf Key](https://expedia.ca/Sugarloaf-Key-Hotels.d183126.Travel-Guide-Hotels)[Flights to Sugarloaf Key](https://expedia.ca/Cheap-Flights-To-Sugarloaf-Key.d183126.Travel-Guide-Flights)[Sugarloaf Key Car Rentals](https://expedia.ca/Car-Rentals-In-Sugarloaf-Key.d183126.Car-Rental-Guide)[Sugarloaf Key Vacation Packages](https://expedia.ca/Sugarloaf-Key.d183126.Destination-Travel-Guides) # What to do in Sugarloaf Key, FL ## Activities, attractions and tours ## Visit Sugarloaf Key Types of activities Where to stay [Sugarloaf Key travel guide](https://expedia.ca/Sugarloaf-Key.dx183126) ![Sugarloaf Key](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/498000/498262-sugarloaf-key.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Sugarloaf Key](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/498000/498223-sugarloaf-key.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Sugarloaf Key](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/498000/498237-sugarloaf-shores.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Sugarloaf Key](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/498000/498224-sugarloaf-shores.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Sugarloaf Key](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/498000/498234-sugarloaf-key.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ## Sugarloaf Key Attractions Let Expedia help you experience the best that Sugarloaf Key has to offer! If you’re looking for fun itinerary ideas, we can provide you with a list of the top sightseeing attractions, as well as helping you to find unmissable activities. Whether you’re travelling with your family, planning a romantic trip with your loved one, or visiting on business, we’ll make it easy to plan an unforgettable holiday that checks all the boxes. #### Activities and Tours Sugarloaf Key is crammed with must-see places to visit and things to do. We can help you decide where to stay, and make it a breeze to explore the surrounding areas with our guides on where to go, what to see and when to see it. No matter how long your stay, it’s easy to find places of interest in Sugarloaf Key to make sure that you enjoy your experience to the fullest and don’t miss a thing. Leave the local knowledge to us and leave the hassle behind. If you’re planning a visit, why not check out our handy guides to places of interest in the area? You can browse lists of things to do, learn about the most popular attractions, and get help with planning the details of your trip. Expedia makes it easy for you to check out all the top sights. #### Sugarloaf Key Attractions Expedia has something for everyone, so whether you’re planning to get active on a summer holiday, put a spring in your step with a romantic rendezvous, or pamper yourself with a leisurely winter trip, you’ll find plenty of attractions to keep you entertained. In addition to scheduling local tours, booking reservations and scoring advance event tickets, Expedia makes it easy to book your flight, hotel and rental car in advance, all on one consolidated travel itinerary, making for hassle-free travel and freeing you up to explore the sights of Sugarloaf Key. Looking for things to do can be time consuming, but we can take the hassle out of planning your holiday. Whether you’re looking to get active in the great outdoors, sample the cuisine or catch up with the vibrant local culture, our guides to Sugarloaf Key attractions ensure that you’ll have a successful trip, whatever the season. * * * Explore thousands of activities with **free cancellation and no added fees**. Design your experience with airport transfers, excursions, day tours & more. Get an insider's look in what to book before you travel. * * * ## 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. [Learn more](https://www.expedia.ca/Duval-Street-Key-West-Historic-District.d6068616.Vacation-Attraction) ![Along one of the southernmost streets in the continental U.S., enjoy a lively area filled with shops, pubs, restaurants and lots of sidewalk acts and vendors.](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/497000/497443-duval-street-key-west.jpg) ### 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. [Learn more](https://www.expedia.ca/Southernmost-Point-Old-Town-Key-West.d501380.Vacation-Attraction) ![Snap a memorable photograph from the edge of North America at this monumental landmark.](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/498000/498010-southernmost-point.jpg) ### 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. [Learn more](https://www.expedia.ca/Mallory-Square-Key-West-Historic-District.d501385.Vacation-Attraction) ![Arrive at this square at day’s end to find street performers, food carts and one of the most beautiful sunsets in the United States.](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/497000/497629-mallory-square.jpg) ### 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. [Learn more](https://www.expedia.ca/Smathers-Beach-Beachside.d6069255.Vacation-Attraction) ![Smathers Beach which includes a luxury hotel or resort, tropical scenes and a beach](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/63000/63912-Smathers-Beach.jpg) ### 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. [Learn more](https://www.expedia.ca/South-Beach-Old-Town-Key-West.d6246827.Vacation-Attraction) ![The southernmost beach in the continental United States is a convenient sandy enclave, just minutes from the center of town.](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/497000/497910-south-beach-fm.jpg) ### 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. [Learn more](https://www.expedia.ca/Ernest-Hemingway-Home-And-Museum-Old-Town-Key-West.d501376.Vacation-Attraction) ![Meet six-toed cats and watch as the life of one America’s great writers unfolds before your eyes at his former home.](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/497000/497554-ernest-hemingway-home-and-museum.jpg) ## Recommended things to do in Sugarloaf Key | Number of things to do | 6 | | --- | --- | | Cheapest thing to do on Expedia | [Guided Clear Kayak Eco-Tour Near Key West](https://expedia.ca/things-to-do/clear-kayak-tours-in-florida-keys.a2599656.activity-details): CA $109 | | Top 5 things to do | - [Guided Clear Kayak Eco-Tour Near Key West](https://expedia.ca/things-to-do/clear-kayak-tours-in-florida-keys.a2599656.activity-details) - [Private Sandbar Adventure in Key West Backcountry](https://expedia.ca/things-to-do/private-sandbar-adventure-in-key-west-backcountry.a47135631.activity-details) - [Golden Glare Fishing Charter with Experienced Captain](https://expedia.ca/things-to-do/golden-glare-fly-charters-llc.a3091255.activity-details) - [Key West Tiki Bar Boat Cruise to Popular Sand Bar](https://expedia.ca/things-to-do/4-hour-private-sand-bar-cruise-on-a-tiki-bar-boat-in-key-west.a3643207.activity-details) - [Full-Day Tour of Florida Keys Including Aquarium Encounters from Key West](https://expedia.ca/things-to-do/full-day-tour-of-florida-keys-including-aquarium-encounters-from-key-west.a1344852.activity-details) | | Half-day tours | - [Guided Clear Kayak Eco-Tour Near Key West](https://expedia.ca/things-to-do/clear-kayak-tours-in-florida-keys.a2599656.activity-details) - [Private Sandbar Adventure in Key West Backcountry](https://expedia.ca/things-to-do/private-sandbar-adventure-in-key-west-backcountry.a47135631.activity-details) | | With kids | - [Guided Clear Kayak Eco-Tour Near Key West](https://expedia.ca/things-to-do/clear-kayak-tours-in-florida-keys.a2599656.activity-details) - [Full-Day Tour of Florida Keys Including Aquarium Encounters from Key West](https://expedia.ca/things-to-do/full-day-tour-of-florida-keys-including-aquarium-encounters-from-key-west.a1344852.activity-details) | ## What to do in Sugarloaf Key * * * ### Discover the most popular places to visit in Sugarloaf Key ![Upper Sugarloaf Sound](https://mediaim.expedia.com/destination/1/af14aeab02ccec9dbe12aecc266935ce.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Upper Sugarloaf Sound Commune with nature and explore the great outdoors at Upper Sugarloaf Sound during your travels in Summerland Key. [](https://expedia.ca/Upper-Sugarloaf-Sound-Sugarloaf-Key.d553248635976195391.Vacation-Attraction) #### Sugarloaf Beach Why not spend a lazy afternoon at Sugarloaf Beach during your trip to Summerland Key? [](https://expedia.ca/Sugarloaf-Beach-Sugarloaf-Key.d553248635983994028.Vacation-Attraction) #### Upper Sugarloaf Key Commune with nature and explore the great outdoors at Upper Sugarloaf Key during your travels in Summerland Key. [](https://expedia.ca/Upper-Sugarloaf-Key-Summerland-Key.d553248635975865768.Vacation-Attraction) ### Explore areas of Sugarloaf Key ![Default Image](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/498000/498222-sugarloaf-key.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Sugarloaf Shores While Sugarloaf Shores isn't home to many top sights, Florida Keys Beaches and Sugarloaf Beach are some notable places to visit nearby. [](https://expedia.ca/Sugarloaf-Key-Sugarloaf-Shores.dx6270983) * * * Looking for fun things to do nearby? Check [things to do near me](https://www.expedia.ca/things-to-do-near-me) to find and book the best things to do, fun activities, and top attractions wherever you happen to be. * * * ## Day trip destinations from Sugarloaf Key ![Key West](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/497000/497918-south-beach-fm.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Key West [](https://expedia.ca/Key-West.dx1187) ![Summerland Key](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/498000/498234-sugarloaf-key.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Summerland Key [](https://expedia.ca/Summerland-Key.dx6177802) ## Frequently asked questions ### Is Sugarloaf Key worth visiting? > Known for its hiking and walking trails, discovering cool things to do in Sugarloaf Key is a breeze. Don't forget to add Florida Keys Beaches to your itinerary when here. ### How do I spend a day in Sugarloaf Key? > When you've checked off key attractions like Florida Keys Beaches and Sugarloaf Beach, spend some time experiencing Sugarloaf Key's retail and dining scene. ### What is the top tourist attraction in Sugarloaf Key? > Florida Keys Beaches is one of the top tourist attractions in Sugarloaf Key and should be high on every itinerary of the area. ### Is three days enough to stay in Sugarloaf Key? > If you just want to see the leading attractions, three days is more than enough time for a trip to Sugarloaf Key. Book for a week or more for the chance to truly appreciate the local vibe, tour nearby highlights and discover some hidden gems. ### Is Sugarloaf Key a walkable city? > Some major attractions in Sugarloaf Key, like Florida Keys Beaches and Sugarloaf Beach, are within walking distance. You can also explore several of the city's neighbourhoods on foot. Just 3 kilometres from central Sugarloaf Key is Lower Sugarloaf Key and Sugarloaf Shores is 2 kilometres away. ### What are some activities to do in Sugarloaf Key with kids? > Planning what to do in Sugarloaf Key with kids is easier than ever. Whether you're getting away with little ones or teenagers, there are loads of family-friendly sights to keep everyone entertained here. > > > > - [Guided Clear Kayak Eco-Tour Near Key West](https://expedia.ca/things-to-do/clear-kayak-tours-in-florida-keys.a2599656.activity-details) > - [Full-Day Tour of Florida Keys Including Aquarium Encounters from Key West](https://expedia.ca/things-to-do/full-day-tour-of-florida-keys-including-aquarium-encounters-from-key-west.a1344852.activity-details) ### What to do in Sugarloaf Key for adults? > Adults of all ages will find lots of things to do in Sugarloaf Key. Whether you're into local cuisine, outdoor activities or just love discovering new places, there's something here for everyone. ### Are there free things to do in Sugarloaf Key? > In Sugarloaf Key, Florida Keys Beaches is a popular spot for anyone planning to see the city without taking their wallet out. Also, stroll around the local parks and neighbourhoods, and ask a local tour guide for ideas. 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