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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The Lower Keys
Sandbar Somewhere Charter
Sandbar Somewhere Charter, led by Captain Hoyt Watkins, offers relaxed inshore and backcountry fishing trips around Summerland Key and Big Pine Key.
Key West
Air Key West
Air Key West offers private, on-demand charters from Key West International Airport, specializing in flights to Cuba, the Bahamas, and throughout Florida.
Key West
Sea Monkey Ocean Adventures
Exciting Key West boat tours and ocean adventures — snorkeling, sunset cruises & more.
Key West
Classic Harbor Line Key West
Sail Key West offers unforgettable sunset and specialty cruises aboard the elegant Schooner America 2.0.
Key West
Key West Sandbar Tours
Escape to hidden sandbars with Key West Sandbar Charters — private boat tours (small or large groups), crystal waters, sun, fun & photo-perfect views.
Islamorada
Pelagic Raptors Charters
Captain Mike runs a 39 foot Contender with triple 300s and a Seakeeper stabilizer out of Islamorada, for up to six anglers. Trips run from four hours to a ten hour swordfish expedition, with tackle and your fishing license included.
Key West
Wall To Wall Fishing Charters
Wall To Wall Fishing Charters — premier private fishing and sandbar tours out of Key West for all ages and experience levels.
Key West
Above & Below Fishing Adventures - Key West & Lower Keys Fishing Charters
Capt. Jose Rodriguez Jr. runs a 2025 32 foot SeaVee out of Cudjoe Key for six anglers, with Starlink, a head aboard and electric reels for deep dropping. In February he put a Pennsylvania family on a 480 pound swordfish after a five hour fight, and most of the community ate swordfish that week.
Key West
Key West Water Tours
Thrilling 2-hour guided jet ski tours exploring stunning Key West waters!
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.
Key West
Cruisin’ Tikis Key West
Cruisin’ Tikis Key West offers fun, BYOB tiki-bar boat cruises—including sunset sails, swim-stop excursions, and eco tours—aboard floating tiki bars navigated by USCG-certified captains.
