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
Keys Boat Tours
Explore Florida Keys' stunning waters with expert-guided boat tours and snorkeling!
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
Ghosts & Gravestones Tour Key West
Nighttime trolley tour revealing Key West’s haunted history, including eerie tales and historic sites.
Key West
Fly-Key West Helicopter Tours
Soar above Key West in a helicopter tour — scenic, adventurous, unforgettable.
Islamorada
Bamboo Charters
Bamboo Charters, led by Captain Matt Bellinger, offers personalized fishing, snorkeling, sandbar, and sunset excursions aboard the "Chubby Mermaid," providing unforgettable experiences in the Florida Keys.
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.
Key West
Fun in the Sun
Fun In The Sun Key West is the home of the original Key West sandbar charter, offering private captained boat charters, bareboat rentals, fishing trips, snorkeling, sunset cruises, boat bar crawls, golf cart rentals, and vacation rentals out of Stock Island Yacht Club with a 5-star TripAdvisor rating.
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.
Islamorada
Why Knot Boat Rentals & Charters
Why Knot Exclusive Rentals — custom boat rentals and captained charters in the Florida Keys for your perfect day on the water.
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.
Key Largo
Caribbean Watersports
Private charters, sails, and snorkeling adventures in the Florida Keys.
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 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.
Marathon
Manic Sportfishing
Manic Sportfishing is a top-rated Florida Keys fishing charter in Marathon offering private offshore, reef, and family-friendly fishing trips with experienced captains and premium boats.
Islamorada
Pretty Work Charters
Pretty Work Charters — full-service fishing charters in Islamorada, FL, where experienced crews and flexible boats deliver unforgettable Florida Keys adventures.
