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
Forever Young Charter Company
Private dive, snorkel, spearfishing & fishing charters in the Florida Keys.
Key West
Old Town Trolley Tours Key West
Key West hop-on/hop-off trolley tour with narrated stops & perks.
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
Cora Beth Fishing
A 60 foot party boat out of C Dock at the Historic Seaport, running five hour reef trips from $75 with a limited load so nobody fishes elbow to elbow. They fillet your catch at the dock and a restaurant around the corner will cook it for you.
Key West
Key West Seaplane Adventures
Soar over crystal waters and land on the Gulf—Key West’s premier seaplane tours to Dry Tortugas and beyond.
Islamorada
Anchors Away Boat Rentals and Tours
Anchors Away Boat Rentals & Tours offers a diverse fleet of over 30 boats, including center consoles, deck boats, and pontoons, available for flexible rentals ranging from 2-hour to monthly durations, with GPS-equipped vessels and optional add-ons like snorkeling gear and GoPro cameras.
Key West
Namaste' Eco Excursions
Namaste’ ECO-Excursions delivers immersive, eco-focused reef and mangrove snorkeling adventures in Key West—small-group, “citizen science” tours with expert guides, coral assessments, and hands-on ecology presentations.
Key West
Blue Horizon Charters
Blue Horizon Charters offers private boat adventures in Key West—ranging from sandbar escapes and snorkeling to sunset cruises—crafted by three lifelong friends passionate about island life and hospitality.
Marathon
Sailing Catamaran Sirius - Ocean Sailing Inc
Sail the Florida Keys on the luxurious 36ft catamaran "Sirius" for unforgettable sunsets.
Marathon
Overseas Aero Tours
Take to the skies over the Florida Keys with Overseas Aero Tours — scenic biplane flights delivering breathtaking views and unforgettable memories.
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.
Key West
Casual Monday Charters
Casual Monday Charters offers private, customizable boat excursions in Key West, featuring sandbar hopping, snorkeling, sunset cruises, and eco tours aboard a 25' Hydrasports center console.
Key Largo
Pirate's Choice Sailing Vessel
Sail Key Largo’s pirate ship for sunset & snorkel adventures
