The best is in Key West starting from the scenic drive from the Florida mainland to the lively nightlife at the end of your day, and all fun-filled activities in between. The best things to do in in Key West include amazing water adventures to enjoy, unique national parks to visit, and delicious food and desserts to eat. Go to Key West to see what all this tiny island has to offer!
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The Best Time to Visit Key West
The best time to visit Key West is when the weather is warm so you can enjoy water activities, but not during the summer or during Spring Break when all the crowds flock to this key. Try visiting in the months of April, May, October, and November for the best weather and the least crowds.
What to Pack for Key West
- Sunscreen – Protect your skin from the sun, and do not forget to reapply.
- Hat – More sun protection to block the sun from your face
- Microfiber Beach Towel – I packed my microfiber beach towel to take to the swimming holes. I didn’t want to bring the hotel towels, and the microfiber towels fold up to practically nothing.
- Swimsuits – For pool or beach time, you will need a swimsuit. Men’s Women’s
- Crochet Beach Bag – This beach bag is great for the beach and also for shopping!
- Cute sundress – A cute sundress is just the thing you need for wine tasting, shopping, and getting those perfect Instagram photos. Check out this one here and another one here.
- Comfy Sneakers – These Dr. Scholls sneakers are both stylish and comfortable for walking around the town! Men’s
- Cell Phone Lanyard – Keep your cell phone safe around your neck!
1. Drive the Best Overseas Highway
Fly into Miami or Fort Lauderdale, rent a car, and drive the nearly 4 hour drive to Key West via the Overseas Highway, or Route 1. This road has recently been named the Jimmy Buffet Memorial Highway. You could fly directly to Key West but then you would miss out on one of the best things to do in Key West. Stop at other keys along the way and make a whole day of it. One possible stop is Key Largo, one of the world’s best scuba diving locations with its coral reefs and shipwrecks to explore. Pull into Robbie’s of Islamorada to feed tarpins.
Another stop along the way is Seven Mile Bridge. This amazing bridge is actually two bridges that cross the colorful waters where the Gulf of Mexico meets the Atlantic Ocean. The newer bridge is open to vehicular traffic, and the older bridge is for pedestrians and cyclists. Finish the drive on Route 1 to its end in Key West.
2. Explore Dry Tortuga National Park
Dry Tortuga National Park, located 70 miles west of Key West, is a 100-square mile park in the United States made of mostly water. It is only accessible by boat or seaplane. Book your reservations EARLY! The ferry tickets sell out months ahead of time during peak tourism seasons.
The park preserves Fort Jefferson, built in the early 1800s to combat piracy in the Caribbean. For interesting facts about this unique park, click here. After exploring the hexagon shaped fortress, spend time snorkeling in the surrounding undisturbed coral reefs. Snorkeling at this national park is by far the best snorkeling spot I have ever witnessed.
3. Eat Key Lime Pie Every Day
Key lime pie was originated in the Florida Keys in the 1850s and is made from Key limes, canned milk, and eggs. The light, fruity, slightly-tart custard pie is a refreshing dessert, especially in the hot summer months of the Florida Keys. When you visit here, get Key lime pie every day. Eating key lime pie is one of the best things to do in Key West, and it something I recommend you do every day! If you don’t like pie, no worries! Most places have key lime pie martini or other key lime-inspired drinks.
4. Visit Ernest Hemingway’s Home
The Ernest Hemingway Home and Museum is one of the most famous historic sites in Key West. Located in Old Town, the Spanish Colonial–style house was home to Ernest Hemingway from 1931 to 1939, during which time he wrote several notable works, including To Have and Have Not. Today, visitors can tour the preserved residence, lush tropical gardens, and the writing studio where Hemingway worked. The property is also known for its population of distinctive six-toed cats, many of which are descendants of Hemingway’s original pet. The museum offers a glimpse into the writer’s life and the years he spent living and writing in Key West.
5. Dine at Sloppy Joe’s
Located at Duval and Greene Street, Sloppy Joe’s has been a popular Key West bar since 1937. The bar owner, Joe Russell, started a speak easy at a different location during the days of Prohibition which was frequented by Ernest Hemingway. After Prohibition ended, the owner moved the bar to Greene Street. Encouraged by Hemingway, the owner changed the name of the bar to Sloppy Joe’s because patrons claimed he ran a sloppy business.
6. Watch for Dolphins
Board a boat tour for close-up dolphin encounters in the Keys. Dolphin watching in this area is amazing and plentiful. Playful dolphins love frolicking in the wake of boats, and it makes for stunning wildlife sightings. As part of this tour, you will also snorkel to see sea life living below the water. If this type of excursion doesn’t interest you, there are plenty of other options for day tours from Key West such as jet skiing or touring the National Wildlife Refuge.
7. See the Southernmost Point of the USA
The Southernmost Point Buoy is one of the most iconic landmarks in Key West and a must-see photo spot. Located at the corner of South Street and Whitehead Street, the large painted buoy marks the southernmost point of the continental United States, just 90 miles from Cuba. Installed in 1983, the colorful concrete marker replaced a simple sign that was frequently stolen by tourists. Today, visitors line up throughout the day to take photos with the buoy’s bright red, black, and yellow stripes. Early morning is the best time to visit if you want to avoid long lines and capture the landmark without crowds.
Unfortunately, the area around the buoy is under construction until late 2026 and cannot be accessed. You can view it temporarily near the Southernmost Beach Resort.
8. Participate in the Pride Community
Key West has long been known for its welcoming and inclusive LGBTQ+ community, making it a popular destination for travelers looking to experience vibrant nightlife and a relaxed, accepting atmosphere. Visitors can easily participate in the local gay scene by exploring the lively bars and clubs along Duval Street, where venues host drag shows, dance parties, and themed events throughout the week. Popular spots like Bourbon Street Pub and Aqua Bar & Nightclub are known for energetic performances and welcoming crowds. Whether attending a show, enjoying cocktails, or meeting new people, visitors often find the atmosphere friendly, festive, and open to everyone. Key West Pride is typically in June and consists of numerous daily events to celebrate the gay community.
9. Shop along Duval Street
Shopping on Duval Street is one of the best things to do in Key West, offering a lively mix of boutiques, souvenir shops, art galleries, and local specialty stores. Stretching from the Gulf of America to the Atlantic Ocean, this famous street is lined with colorful storefronts where visitors can browse everything from beachwear and handmade jewelry to tropical home décor and locally made art. Stores like Key West Aloe and Kermit’s Key West Key Lime Shoppe offer unique island-inspired products. With street performers, cafés, and historic buildings along the way, shopping here feels like part of the Key West experience.
10. Party in the Keys
Key West is famous for its laid-back but lively party scene, especially along Duval Street. As the sun sets, bars and clubs fill with live music, tropical cocktails, and dancing that often lasts well past midnight. Popular spots like Sloppy Joe’s Bar and Rick’s Bar are known for energetic crowds and multiple music venues under one roof. There are also breweries and distilleries you can visit while you are here such as the Waterfront Brewery and Papa Pilar’s Run Distillery. Whether you prefer relaxed beachside drinks or a full night of dancing, Key West offers something for every kind of partygoer.
11. Watch the Sunset at Mallory Square
Mallory Square is one of the most famous gathering places in Key West, Florida, located along the waterfront at the western edge of Old Town. Overlooking the Gulf of Mexico, the historic square is best known as the home of the island’s nightly Sunset Celebration, a tradition that draws locals and visitors together every evening.
About two hours before sunset, the square comes alive with street performers, musicians, and local artisans setting up booths along the docks. Visitors can watch magicians, jugglers, and fire performers while browsing handmade crafts or sampling snacks from food vendors.
As the sun begins to sink toward the horizon, the crowd gathers along the waterfront to watch the sky turn shades of pink, orange, and gold over the Gulf of Mexico. When the sun finally dips below the water, applause often breaks out among the spectators, marking the end of another day in true Key West style. Free and held every night of the year (weather permitting), the Sunset Celebration captures the laid-back, artistic spirit that defines the island.
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