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
Ghosts & Gravestones Tour Key West
Nighttime trolley tour revealing Key West’s haunted history, including eerie tales and historic sites.
Islamorada
Reef Roamer Catamaran Snorkel Sail
Reef Roamer Catamaran Snorkel Sail is a family-owned, 44-foot sailing catamaran that has run reef trips from Old Conch Harbor in Tavernier since 2006. It offers morning and afternoon snorkel sails plus a sunset sail, with gear included and an easy staircase ladder that lets snorkelers of all ages get into the water.
Key West
Keys Seaplanes
Fly in style over Florida’s waters — Keys Seaplanes offers private amphibious charters and scenic flights across the Keys.
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
The Water Traveler Vacations
The Water Traveler is your luxury guide to private boat charters, all-inclusive captained getaways, and bespoke waterfront events.
Marathon
Fishing Kings
Marathon Fishing Kings — private reef, wreck & offshore fishing charters in Marathon, where expert guidance meets trophy-fish potential.
Islamorada
Why Knot Boat Rentals & Charters
Why Knot Exclusive Rentals — custom boat rentals and captained charters in the Florida Keys for your perfect day on the water.
Key West
Up The Keys Tours
Up The Keys — immersive land-based eco-tours through the Florida Keys with expert local guides and scenic drives along the Overseas Highway.
Key Largo
African Queen
African Queen — historic steamboat canal cruises in Key Largo, made famous by the 1951 film with Humphrey Bogart and Katharine Hepburn.
Marathon
Crazy Banana Charter
Premier private fishing charters and scenic sunset cruises in Marathon and the Florida Keys — target mahi, tuna, wahoo and more with expert captains.
Key West
Key West Water Tours
Thrilling 2-hour guided jet ski tours exploring stunning Key West waters!
Key Largo
Key Largo Parasail
USCG-certified parasail adventures: soar over Key Largo’s waters in style.
