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
WILD about DOLPHINS-Captain Sheri's
Wild About Dolphins — private eco-boat tours and wild dolphin encounters departing from Key West, Florida.
The Lower Keys
Rippin Line Charters
Explore Florida Keys waters with Captain Anthony—fishing, eco tours, and sunset cruises!
Key Largo
Capt. Sterling's Everglades Tour
Captain Sterling's Everglades Eco-Tours offers personalized, small-group boat excursions through the Everglades National Park, Pennekamp Park, and Florida Bay, led by experienced guides passionate about wildlife conservation.
Islamorada
Reef Quest Tours
ReefQuest Tours: Explore the vibrant reefs, wildlife, and sandbars of the Florida Keys on tailor-made, eco-educational boat adventures.
Marathon
Fly Heli Florida Keys
Soar over the stunning Florida Keys with Fly Heli Tours for breathtaking island views!
Islamorada
Morada Mermaid Adventures
The Morada Mermaid is a scenic charter boat experience in the Florida Keys offering sunset cruises, sandbar escapes, and island adventures from Marathon and Islamorada, FL.
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
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.
Islamorada
Reef Roamer Catamaran Snorkel Sail
Reef Roamer is a family-owned 44-foot sailing catamaran based in Tavernier, sailing to shallow, marine-packed reefs in the Florida Keys National Marine Sanctuary. Flat, stable, and easygoing, it is built for snorkelers of every age and skill level, from young kids to grandparents, with fully sanitized gear and a friendly local crew.
Key West
Sebago Watersports
Top-rated Key West watersports & sailing tours — snorkeling, sunset sails, parasailing & more.
Key Largo
Morning Star Sailing Charters
Morning Star Sailing Charters offers personalized sailing experiences in the Florida Keys, including captained and bareboat charters, sunset cruises, and snorkeling tours.
Key West
CN-it Adventures
CN-IT Adventures offers personalized boat excursions in Key West aboard a 26-foot Twin Vee, delivering custom eco-tours, snorkeling, and island hopping catered to your preferences and weather conditions.
Key West
Adventures Key West
Adventures Key West is a full-service Key West experience booking company curated by local experts, offering everything from on-water adventures and private charters to golf cart and scooter rentals, cultural workshops, wellness experiences, and private event and wedding bookings throughout Key West.
Weddings Max
200
Key Largo
Key Largo Princess Glass Bottom Boat
Glass-bottom cruises over Molasses Reef—see the reef without getting wet.
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.
