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
Captain Hook's Dive Key West
Captain Hook's Dive Key West is a full-service dive shop offering scuba diving, snorkeling, and private charters.
Key West
Six Fins Charters
Private luxury boat and jet ski charters in Key West — explore hidden reefs, sandbars, and dolphin playgrounds.
Islamorada
Florida Keys Watersports
Boat & jet ski rentals + tours exploring reefs, mangroves & sandbars in Islamorada.
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
Captain Stewys Charters
Captain Stewy's Charters offers private, personalized boat excursions in Key Largo, specializing in snorkeling trips, sandbar tours, eco tours, and sunset cruises for up to six guests.
Marathon
Keys Jet Ski & Boat Rentals
High-octane jet ski rentals and guided water adventures in the Florida Keys.
Key West
Bear Holeman Charters
Bear Holeman offers expert inshore and offshore fishing charters in Key West, with captains boasting over 20 years of experience and ready-to-use gear for families, solo anglers, and seasoned fishers.
Key West
Island Vibe Charters
Private Key West boat charters: sandbars, reefs & sunshine memories await.
Key West
After Hours Yacht
Private yacht charters in Key West for unforgettable sunset cruises and day trips.
Key West
Life On The Rocks Charters
Life on the Rocks Charters offers fun, customizable boat trips around Key West—sandbar hopping, snorkeling, sunset cruises, and more.
Key West
Rusty's Bucket Charters
Rusty's Bucket Charters offers private fishing trips, snorkeling, sunset cruises, and sandbar adventures aboard a 24' Sea Hunt center console. Led by Captain Russ, they provide a hands-on experience for up to six guests, with trips tailored to your preferences.
The Lower Keys
Snapshot Charters
Family-friendly Snapshot Charters offers unforgettable reef to swordfish fishing trips!
The Lower Keys
WILD about DOLPHINS-Captain Sheri's
Wild About Dolphins — private eco-boat tours and wild dolphin encounters departing from Key West, Florida.
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.
