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
Walk The Plank Adventures LLC
Walk The Plank Adventures — private sandbar, island and sunset boat tours departing from Key West.
Marathon
Sailing Catamaran Sirius - Ocean Sailing Inc
Sail the Florida Keys on the luxurious 36ft catamaran "Sirius" for unforgettable sunsets.
Key Largo
Island Ventures
Explore Key Largo's vibrant reefs with private, expert-led scuba and snorkel tours!
Islamorada
Florida Keys Watersports
Boat & jet ski rentals + tours exploring reefs, mangroves & sandbars in Islamorada.
Marathon
Z Flight Watersports | Marathon FL
Zip into the sky with Z-Flight Watersports: parasailing thrills await.
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
Anchors Away Boat Rentals and Tours
Anchors Away Boat Rentals & Tours offers a diverse fleet of over 30 boats, including center consoles, deck boats, and pontoons, available for flexible rentals ranging from 2-hour to monthly durations, with GPS-equipped vessels and optional add-ons like snorkeling gear and GoPro cameras.
Islamorada
Coral Keys Adventures
Coral Keys Adventures, founded by longtime Islamorada captain Rebekah Susa, offers immersive boat tours that blend snorkeling, history, and adventure at iconic sites like Alligator Lighthouse and Indian Key.
Islamorada
Z Flight Watersports | Islamorada FL
Soar with Z-Flight Watersports—book your unforgettable adventure today.
The Lower Keys
Sandbar Somewhere Charter
Sandbar Somewhere Charter, led by Captain Hoyt Watkins, offers relaxed inshore and backcountry fishing trips around Summerland Key and Big Pine Key.
Islamorada
Forever Young Charter Company
Private dive, snorkel, spearfishing & fishing charters in the Florida Keys.
Islamorada
Clearly Unique Charters
Clearly Unique Charters offers snorkeling, sandbar, and sunset boat tours in Islamorada aboard spacious powerboats designed for family fun and special events.
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.
Islamorada
Morada Mermaid Adventures
The Morada Mermaid is a scenic charter boat experience in the Florida Keys offering sunset cruises, sandbar escapes, and island adventures from Marathon and Islamorada, FL.
