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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Islamorada
Florida Keys Boat Rentals, Jetski & Island Tours
Boat & jetski rentals, island & state park tours in Islamorada from Robbie’s Marina.
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.
Key West
Argo Navis Key West Sailing Charters
Argo Navis is a 75-foot luxury catamaran offering intimate, all-inclusive sailing experiences in Key West, including sunset cruises, brunch sails, and private charters, with curated food and drink pairings.
Key West
Dauntless Excursions
Dauntless Excursions offers private, customizable charters from Key West, featuring activities like lobstering, snorkeling, reef fishing, and sandbar hopping aboard the 32-foot Dauntless vessel.
Islamorada
Islamorada Fishing Charters Florida Keys
Offshore and inshore sportfishing charters in Islamorada.
Key West
Sea Monkey Ocean Adventures
Exciting Key West boat tours and ocean adventures — snorkeling, sunset cruises & more.
Islamorada
Coastal Outfitters Sport Fishing Charters
Coastal Outfitters offers customized fishing charters and sunset cruises in Islamorada, delivering relaxed, captained outings tailored to your preferences.
Marathon
SS Pops Two Conchs Island Tours
Explore stunning Florida Keys boat tours with Two Conchs Island Tours!
Marathon
Fishing Kings
Marathon Fishing Kings — private reef, wreck & offshore fishing charters in Marathon, where expert guidance meets trophy-fish potential.
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
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 Largo
Island Ventures
Explore Key Largo's vibrant reefs with private, expert-led scuba and snorkel tours!
Key Largo
Saltwater Cowboy Charterz
Experience unforgettable fishing and snorkeling adventures in Key Largo with Saltwater Cowboy Charterz.
Islamorada
Reef Quest Tours
ReefQuest Tours: Explore the vibrant reefs, wildlife, and sandbars of the Florida Keys on tailor-made, eco-educational boat adventures.
