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.

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.

Key Largo

Pirate's Choice Sailing Vessel

Sail Key Largo’s pirate ship for sunset & snorkel adventures

Islamorada

Islamorada Fishing Charters Florida Keys

Offshore and inshore sportfishing charters in Islamorada.

Islamorada

Chris Clearwater Charters

Chris Clearwater Charters: Custom fishing, snorkeling & sandbar adventures with a chef-captain in the Florida Keys.

Marathon

Florida Keys Flight Academy

Fly above the Keys—learn, explore & tour with Florida Keys Flight Academy.

Key West

Florida Keys Flight Academy Key West

Florida Keys Flight Academy — flight training and scenic tours in Marathon, where aspiring pilots and adventure seekers soar over the stunning Florida Keys.

The Lower Keys

Keys Boat Tours

Explore Florida Keys' stunning waters with expert-guided boat tours and snorkeling!

Marathon

Marathon Mermaid Charters

Marathon Mermaid Charters offers sunset cruises, sandbar adventures, and reef snorkeling trips from Marathon, FL — fun for all ages.

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

Old Town Trolley Tours Key West

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

Key West

Screaming Lines Adventures

Four generations of Estenoz heritage leading sportfishing adventures in Key West’s waters.

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.

Key Largo

Pirates Cove Watersports

Pirates Cove Watersports, located at Reefhouse Resort & Marina in Key Largo, is a top-rated watersports hub offering jet ski rentals, scuba diving & snorkeling, parasailing, eco-tours, sunset cruises, dolphin swims, fishing charters, and more—all under one roof.