Experiences

As the sun begins its descent, Mallory Square transforms into a lively open-air theater of street performers, local artisans, and vibrant island energy. The nightly Sunset Celebration is a Key West tradition, where fire jugglers, tightrope walkers, and musicians entertain against a backdrop of glowing skies. Wander from vendor to vendor, sip something refreshing, and watch as the horizon puts on its own show. It’s festive, free-spirited, and pure Key West.

Key West’s shopping scene is as vibrant and eclectic as the island itself. Stroll through charming boutiques, art galleries, and specialty shops showcasing everything from handcrafted jewelry and island-inspired fashion to colorful artwork and unique home decor. Whether you’re searching for the perfect keepsake or simply soaking in the lively local atmosphere, shopping here offers an authentic slice of island creativity and charm.

Mark your visit at the iconic Southernmost Point buoy, a vibrant landmark perched at the edge of the island. This colorful spot serves as one of the top attractions in the Keys, as well as one of the most photographed. Nearby, you’ll find charming streets to explore, filled with historic architecture, local cafes, and the unmistakable buzz of island life. It’s a must-see that perfectly captures the heart of the Keys.

Whether you want to book a leisurely day sail with Key West Sailing Charter or a snorkeling trip to nearby reefs with Fury Water Adventures, there’s plenty of local options to choose from. Imagine savoring freshly pulled lobster right on your boat as you cruise past hidden coves or drop anchor at a secluded sandbar for a peaceful escape. Boating here offers a perfect blend of adventure and tranquility, as well as a true taste of island living.

Dive into the fascinating history of shipwrecks and treasure hunting at the Mel Fisher Maritime Museum. Named after the legendary treasure hunter, the museum showcases artifacts recovered from sunken Spanish galleons, including stunning gold and silver treasures, navigational tools, and relics that tell stories of the sea. It’s a captivating glimpse into Key West’s maritime past and a must-visit for history buffs and curious travelers alike.

One of the island’s oldest attractions, the Key West Aquarium offers an up-close look at the marine life that calls the Florida Keys home. Explore exhibits featuring stingrays, sea turtles, sharks, and colorful reef fish, and don’t miss the interactive touch tank – a favorite for all ages. With daily feeding shows and guided tours, the aquarium blends education and entertainment in a charming, historic setting right on the waterfront.

Looking for some after-dark Key West activities beyond the bar scene? Try out a guided glow kayak tour through Key West’s calm, shallow waters. Outfitted with LED-lit clear-bottom kayaks, Night Kayak Key West offers a one-of-a-kind view into the marine world after dark. As you glide across mangrove-lined channels, you might spot tropical fish, stingrays, or even curious nurse sharks beneath your boat. Peaceful, surreal, and just a little bit magical, it’s a truly memorable way to see the island from a new perspective.

Step back in time with a visit to the Harry S. Truman Little White House, the former winter retreat of the 33rd U.S. president. Nestled in the heart of Old Town, this historic residence offers guided tours filled with behind-the-scenes stories, original furnishings, and insights into Truman’s time on the island. It’s a peaceful, palm-shaded property that gives a fascinating glimpse into Key West’s presidential past, and a quieter side of American history.

From dockside seafood spots to candlelit bistros, Key West’s dining scene is bursting with flavor and character. Start with Latitudes, Sunset Key’s own award-winning restaurant known for island-inspired cuisine served just steps from the sand. Then explore off-island favorites like Blue Heaven, a funky outdoor café beloved for its Caribbean flair and live music, or Garbo’s Grill, a food truck tucked behind a bar serving up bold, fresh flavors. Wherever you dine, expect the catch of the day, Key lime pie, and plenty of local charm on the menu.