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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Marathon
Island Girl Charters
Experience unforgettable Florida Keys adventures with Island Girl Charters—fishing, snorkeling, and more!
Key West
Casual Monday Charters
Casual Monday Charters offers private, customizable boat excursions in Key West, featuring sandbar hopping, snorkeling, sunset cruises, and eco tours aboard a 25' Hydrasports center console.
Key West
Air Key West
Air Key West offers private, on-demand charters from Key West International Airport, specializing in flights to Cuba, the Bahamas, and throughout Florida.
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.
Key West
Key West Coastal Charters
Set sail with Key West Coastal Charters and discover Key West’s famous sandbars on private charters full of snorkeling, dolphin-watching, nature, fishing & more.
Marathon
Florida Keys Flight Academy
Fly above the Keys—learn, explore & tour with Florida Keys Flight Academy.
Key West
Dauntless Excursions
Dauntless Excursions offers private, customizable charters from Key West, featuring activities like lobstering, snorkeling, reef fishing, and sandbar hopping aboard the 32-foot Dauntless vessel.
Islamorada
Pretty Work Charters
Pretty Work Charters — full-service fishing charters in Islamorada, FL, where experienced crews and flexible boats deliver unforgettable Florida Keys adventures.
Key Largo
Key Largo Princess Glass Bottom Boat
Glass-bottom cruises over Molasses Reef—see the reef without getting wet.
Marathon
Two Conchs Fishing Charters
A family-run charter fleet led by Capt. Jack Carlson, offering 20+ boats across The Florida Keys.
Marathon
Fishing Kings
Marathon Fishing Kings — private reef, wreck & offshore fishing charters in Marathon, where expert guidance meets trophy-fish potential.
Key West
Captain Conch Charters
Captain Conch Charters offers customizable fishing experiences in Key West, including split, private, and party boat charters, targeting species like mahi mahi, tuna, and sharks.
Key West
Key West Express
Key West Express — high‑speed ferry service from Fort Myers Beach and Marco Island to Key West for relaxing day trips or island adventures.
