Model train and figure in a colorful outdoor theme park setting.

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

Old Town Trolley Tours Key West

Key West hop-on/hop-off trolley tour with narrated stops & perks.

Islamorada

Allergic to Land Charters

Discover Islamorada's waters with Captain Sue—snorkel, sunset, eco tours.

Key West

Key West Seaplane Adventures

Soar over crystal waters and land on the Gulf—Key West’s premier seaplane tours to Dry Tortugas and beyond.

Islamorada

Reef Marine

Boat rentals, snorkel & fishing charters across the Florida Keys

Key West

Historic Tours of America

Trolley + walking historic tours of Key West.

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

Florida Keys Watersports

Boat & jet ski rentals + tours exploring reefs, mangroves & sandbars in Islamorada.

Key West

Yankee Freedom Dry Tortugas Ferry

Dry Tortugas National Park — remote Florida Keys paradise 70 miles west of Key West featuring historic Fort Jefferson, turquoise water, pristine beaches and world-class snorkeling.

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.

Marathon

Fishing Kings

Marathon Fishing Kings — private reef, wreck & offshore fishing charters in Marathon, where expert guidance meets trophy-fish potential.

Key West

Walk The Plank Adventures LLC

Walk The Plank Adventures — private sandbar, island and sunset boat tours departing from Key West.

Key Largo

Key Largo Princess Glass Bottom Boat

Glass-bottom cruises over Molasses Reef—see the reef without getting wet.

Key West

Green Turtle Charters

Private charters in Key West offering sandbar trips, snorkeling, eco-tours, and dolphin watching.

Key West

After Hours Yacht

Private yacht charters in Key West for unforgettable sunset cruises and day trips.