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
Key West Coastal Charters
Set sail with Key West Coastal Charters and discover Key West’s famous sandbars on private charters full of snorkeling, dolphin-watching, nature, fishing & 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.
Key West
Aloha Sailing Key West
Personalized sailing charters aboard a Fountaine Pajot catamaran, exploring the Florida Keys and Dry Tortugas.
Key West
Sea Monkey Ocean Adventures
Exciting Key West boat tours and ocean adventures — snorkeling, sunset cruises & more.
Key West
Old Town Trolley Tours Key West
Key West hop-on/hop-off trolley tour with narrated stops & perks.
Marathon
Custom Cat Charters
Custom Cat Charters offers tailored private boat trips for fishing, sightseeing, and special events in the Florida Keys.
Islamorada
Sandy Bottom Charters
Sandy Bottom Charters offers personalized private boat charters in the Florida Keys for snorkeling, sandbar trips, and sunset cruises.
Key West
Walk The Plank Adventures LLC
Walk The Plank Adventures — private sandbar, island and sunset boat tours departing from Key West.
Marathon
Fishing Kings
Marathon Fishing Kings — private reef, wreck & offshore fishing charters in Marathon, where expert guidance meets trophy-fish potential.
Key Largo
Pirate's Choice Sailing Vessel
Sail Key Largo’s pirate ship for sunset & snorkel adventures
Key Largo
Tropic Ocean Airways
Tropic Ocean Airways — seaplane and charter flight service across Florida & the Bahamas, where effortless skies meet elevated coast-to-coast travel.
Islamorada
Latitude Charters
Private boat charters in the Upper Keys — sandbar trips, sunset cruises, snorkeling & special-occasion charters.
Marathon
Florida Keys Flight Academy
Fly above the Keys—learn, explore & tour with Florida Keys Flight Academy.
