Sightseeing
From quirky tours to can’t-miss landmarks, sightseeing in The Florida Keys is anything but ordinary - on island or at sea. Hop on a trolley or the iconic Conch Train, set sail on a charter, or wander museums filled with history, art, and stories you couldn’t make up if you tried. Key West’s haunted tours add a spooky thrill, while scenic drives and hidden stops up and down the island chain reveal the Keys’ offbeat charm. These listings connect you with the guides, tours, and attractions that turn “just looking around” into a true island adventure.
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Key West
Reel Fresh Fishing
Reel Fresh Fishing — private fishing charters in Key West, where expert captains and top-tier gear deliver unforgettable deep-sea, reef and wreck experiences.
Islamorada
Easy Livin' Charter Boat
Custom boat tours and fishing adventures with local legend Captain Augie in Islamorada.
The Lower Keys
WILD about DOLPHINS-Captain Sheri's
Wild About Dolphins — private eco-boat tours and wild dolphin encounters departing from Key West, Florida.
Key West
Island Vibe Charters
Private Key West boat charters: sandbars, reefs & sunshine memories await.
Islamorada
Coastal Outfitters Sport Fishing Charters
Coastal Outfitters offers customized fishing charters and sunset cruises in Islamorada, delivering relaxed, captained outings tailored to your preferences.
Key Largo
Caribbean Watersports
Private charters, sails, and snorkeling adventures in the Florida Keys.
Islamorada
Bamboo Charters
Bamboo Charters, led by Captain Matt Bellinger, offers personalized fishing, snorkeling, sandbar, and sunset excursions aboard the "Chubby Mermaid," providing unforgettable experiences in the Florida Keys.
Islamorada
Lightly Salted Charters
Private Islamorada boat tours: snorkel, sandbar, fishing—book your adventure.
Key West
Reel Paradise Charters
Experience unforgettable days on the water in the Florida Keys with private and shared charters from Key West.
Key Largo
Capt. Sterling's Everglades Tour
Captain Sterling's Everglades Eco-Tours offers personalized, small-group boat excursions through the Everglades National Park, Pennekamp Park, and Florida Bay, led by experienced guides passionate about wildlife conservation.
Key West
Cora Beth Fishing
Cora Beth Fishing offers personalized, limited-load party boat and private fishing charters from Key West Bight Marina.
Marathon
Overseas Aero Tours
Take to the skies over the Florida Keys with Overseas Aero Tours — scenic biplane flights delivering breathtaking views and unforgettable memories.
Marathon
Nautica Watersports
Thrilling jet ski adventures and serene sunset rides in Marathon, Florida.
Key West
Your Island Charter
Your Island Charter — private boat charters for sandbars, snorkeling, fishing and sunsets in the Florida Keys.
Key West
Blu Q Catamaran
Blu Q Catamaran offers unique, clothing-optional sailing experiences in Key West, featuring all-male day trips, sunset sails, and private charters aboard their 42-foot catamaran.
