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
Sunset Watersports Parasail 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.
Islamorada
Coastal Outfitters Sport Fishing Charters
Coastal Outfitters offers customized fishing charters and sunset cruises in Islamorada, delivering relaxed, captained outings tailored to your preferences.
Key Largo
Cruisin’ Tikis Key Largo
Cruisin’ Tikis Key Largo offers quirky tiki-bar boat cruises—ranging from fun daytime outings to romantic sunset sails and seasonal night tours—departing dockside at Snook’s Bayside in Key Largo.
Islamorada
Islamorada Fishing Charters Florida Keys
Offshore and inshore sportfishing charters in Islamorada.
Marathon
Florida Keys Flight Academy
Fly above the Keys—learn, explore & tour with Florida Keys Flight Academy.
Key West
Second Generation Fishing Charters
We Fish Key West — your local charter partner for top offshore, reef, and backcountry fishing adventures.
Key Largo
Pirate's Choice Sailing Vessel
Sail Key Largo’s pirate ship for sunset & snorkel adventures
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.
Islamorada
Glass Bottom Boats of Islamorada
See Florida Keys marine life through a clear-bottom boat tour.
The Lower Keys
Rippin Line Charters
Explore Florida Keys waters with Captain Anthony—fishing, eco tours, and sunset cruises!
Key West
FishMonster & IslandJane Charters
Key West’s premier fishing and adventure charters, offering everything from party boat fishing to private eco-tours and sunset sails.
Key West
Island Vibe Charters
Private Key West boat charters: sandbars, reefs & sunshine memories await.
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.
Key West
Six Fins Charters
Private luxury boat and jet ski charters in Key West — explore hidden reefs, sandbars, and dolphin playgrounds.
