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
Tiki Boat Adventures Key West Sandbar Charters
Tiki Boat Adventures — private tiki-bar boat charters in Key West for sandbars, sunsets & island-style fun.
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
Sailing Catamaran Sirius - Ocean Sailing Inc
Sail the Florida Keys on the luxurious 36ft catamaran "Sirius" for unforgettable sunsets.
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.
Marathon
Fishing Kings
Marathon Fishing Kings — private reef, wreck & offshore fishing charters in Marathon, where expert guidance meets trophy-fish potential.
Islamorada
Florida Keys Boat Rentals, Jetski & Island Tours
Boat & jetski rentals, island & state park tours in Islamorada from Robbie’s Marina.
Islamorada
Bluewater Adventure
Bluewater Adventure – The Keys offers guided two-person catamaran tours in Islamorada, allowing guests to drive their own boat while exploring the scenic waterways of the Florida Keys.
Marathon
Custom Cat Charters
Custom Cat Charters offers tailored private boat trips for fishing, sightseeing, and special events in the Florida Keys.
Key Largo
Cruisin’ Tikis Key Largo
Cruisin’ Tikis Key Largo offers quirky tiki-bar boat cruises—ranging from fun daytime outings to romantic sunset sails and seasonal night tours—departing dockside at Snook’s Bayside in Key Largo.
Marathon
Z Flight Watersports | Marathon FL
Zip into the sky with Z-Flight Watersports: parasailing thrills await.
Key West
Classic Harbor Line Key West
Sail Key West offers unforgettable sunset and specialty cruises aboard the elegant Schooner America 2.0.
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.
Islamorada
Allergic to Land Charters
Discover Islamorada's waters with Captain Sue—snorkel, sunset, eco tours.
Key West
Rusty's Bucket Charters
Rusty's Bucket Charters offers private fishing trips, snorkeling, sunset cruises, and sandbar adventures aboard a 24' Sea Hunt center console. Led by Captain Russ, they provide a hands-on experience for up to six guests, with trips tailored to your preferences.
