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
Rippin Line Charters
Explore Florida Keys waters with Captain Anthony—fishing, eco tours, and sunset cruises!
Key West
Key West Express
Key West Express — high‑speed ferry service from Fort Myers Beach and Marco Island to Key West for relaxing day trips or island adventures.
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.
Islamorada
Bluewater Adventure
Bluewater Adventure – The Keys offers guided two-person catamaran tours in Islamorada, allowing guests to drive their own boat while exploring the scenic waterways of the Florida Keys.
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
Yankee Freedom Dry Tortugas Ferry
Dry Tortugas National Park — remote Florida Keys paradise 70 miles west of Key West featuring historic Fort Jefferson, turquoise water, pristine beaches and world-class snorkeling.
Marathon
Fly Heli Florida Keys
Soar over the stunning Florida Keys with Fly Heli Tours for breathtaking island views!
Key West
Blu Q Catamaran
Blu Q Catamaran offers unique, clothing-optional sailing experiences in Key West, featuring all-male day trips, sunset sails, and private charters aboard their 42-foot catamaran.
Key West
Dolphin Safari Charters Key West
Dolphin Safari Charters offers small-group dolphin watching, snorkeling and private boat charters departing from Stock Island near Key West.
Marathon
Z Flight Watersports | Marathon FL
Zip into the sky with Z-Flight Watersports: parasailing thrills await.
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
Islamorada
A Family Fun Boat Tour Company
Load up your crew, your cooler and even your dog, then hand the wheel to a Coast Guard certified captain for a private day on the water out of Islamorada. Snorkel the reef, wade out on the sandbar, watch for dolphins in the mangroves or drift through sunset, and the day is yours to build.
