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
Classic Harbor Line Key West
Sail Key West offers unforgettable sunset and specialty cruises aboard the elegant Schooner America 2.0.
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
Florida Keys Boat Rentals, Jetski & Island Tours
Boat & jetski rentals, island & state park tours in Islamorada from Robbie’s Marina.
Marathon
Custom Cat Charters
Custom Cat Charters offers tailored private boat trips for fishing, sightseeing, and special events in the Florida Keys.
Key West
The Water Traveler Vacations
The Water Traveler is your luxury guide to private boat charters, all-inclusive captained getaways, and bespoke waterfront events.
Key West
Reel Fresh Fishing
Reel Fresh Fishing — private fishing charters in Key West, where expert captains and top-tier gear deliver unforgettable deep-sea, reef and wreck experiences.
Key West
Sebago Watersports
Top-rated Key West watersports & sailing tours — snorkeling, sunset sails, parasailing & more.
Key West
Key West Seaplane Adventures
Soar over crystal waters and land on the Gulf—Key West’s premier seaplane tours to Dry Tortugas and beyond.
Marathon
Salt Dance Boat Tours
Custom private boat excursions in Marathon with sandbar trips, snorkeling adventures, and sunset cruises on a pet-friendly deck boat for families and friends.
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.
Marathon
Z Flight Watersports | Marathon FL
Zip into the sky with Z-Flight Watersports: parasailing thrills await.
Marathon
Florida Keys Flight Academy
Fly above the Keys—learn, explore & tour with Florida Keys Flight Academy.
