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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Islamorada
Coral Keys Adventures
Coral Keys Adventures, founded by longtime Islamorada captain Rebekah Susa, offers immersive boat tours that blend snorkeling, history, and adventure at iconic sites like Alligator Lighthouse and Indian Key.
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.
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.
Islamorada
Easy Livin' Charter Boat
Custom boat tours and fishing adventures with local legend Captain Augie in Islamorada.
Key West
Captain Hook's Dive Key West
A NOAA Blue Star dive operator running two trips a day out to the Vandenberg, Sand Key Lighthouse and the reefs off Key West, with a divemaster in the water on every dive. Snorkelers get their own departures and all the gear, and no experience is required.
Islamorada
Glass Bottom Boats of Islamorada
See Florida Keys marine life through a clear-bottom boat tour.
Key Largo
Key Largo Tiki Tours
Float, sip & unwind—tiki cruises and private charters in Key Largo’s waters.
Key West
FishMonster & IslandJane Charters
A family run outfit fishing Key West since 2006, with boats at three Old Town docks: a 64 foot air conditioned catamaran running $85 half day party trips, a fleet of sportfishers, and a 52 foot sailing ketch for sunset charters and weddings. Fishing license and bait come included in the party boat fare.
Key West
Fishy Business Charters
Offshore, reef, and backcountry fishing charters aboard a 36’ Front Runner Center Console with Captain Eric Evans.
Key West
Blue Horizon Charters
Blue Horizon Charters offers private boat adventures in Key West—ranging from sandbar escapes and snorkeling to sunset cruises—crafted by three lifelong friends passionate about island life and hospitality.
Islamorada
Deep Sea Scuba
Deep Sea Scuba & Snorkel in Islamorada offers top-quality personalized scuba diving, snorkeling, eco-tours, PADI training, and six-pack charters, all backed by over 25 years of safety-focused experience.
Key Largo
Eye Catcher Charters
Private fishing, snorkeling & sunset charters aboard a 30' Sea Hunt with Captain Bry.
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
Sandy Bottom Charters
Sandy Bottom Charters offers personalized private boat charters in the Florida Keys for snorkeling, sandbar trips, and sunset cruises.
