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
Aloha Sailing Key West
Personalized sailing charters aboard a Fountaine Pajot catamaran, exploring the Florida Keys and Dry Tortugas.
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
Brightwild Adventures
Brightwild Adventures offers personalized boat excursions in Key West, including family and adult sandbar trips, sunset cruises, private charters, and golf cart rentals, all tailored to your preferences.
Key West
Sunset Watersports Key West
Sunset Watersports is Key West’s oldest and most trusted watersports provider, offering parasailing, snorkeling, jet ski tours, sunset dinner cruises, and more.
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
A Family Fun Boat Tour Company
Family Fun Boat Tours offers private, kid-friendly boating adventures for up to 12 guests in the Upper Florida Keys—perfect for snorkeling, eco-tours, sandbar visits, sightseeing, or sunset cruises.
Marathon
SS Pops Two Conchs Island Tours
Explore stunning Florida Keys boat tours with Two Conchs Island Tours!
Islamorada
Islamorada Turtle Tours
Sandbar trips, snorkeling, sunset cruises & private charters in Islamorada.
Key Largo
Key Largo Tiki Tours
Float, sip & unwind—tiki cruises and private charters in Key Largo’s waters.
Marathon
Sweet E'Nuf Charters
Experience top fishing adventures in Marathon, FL with expert captains and unforgettable catches!
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
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.
Marathon
Custom Cat Charters
Custom Cat Charters offers tailored private boat trips for fishing, sightseeing, and special events in the Florida Keys.
Islamorada
Reel Attack Charters
Reel Attack Charters — full-service fishing charters in Islamorada, where expert guides, big catches and unforgettable Florida Keys experiences converge.
