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
Cruisin’ Tikis Key West
Cruisin’ Tikis Key West offers fun, BYOB tiki-bar boat cruises—including sunset sails, swim-stop excursions, and eco tours—aboard floating tiki bars navigated by USCG-certified captains.
Key West
Sebago Watersports
Top-rated Key West watersports & sailing tours — snorkeling, sunset sails, parasailing & more.
Key West
Above & Below Fishing Adventures - Key West & Lower Keys Fishing Charters
Above & Below Fishing Adventures offers private, all-in-one Florida Keys charters—fishing, snorkeling, sunset cruises, spearfishing, lobster diving, and more—with full gear, Starlink Wi-Fi, and expert guides.
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.
Islamorada
Florida Keys Boat Rentals, Jetski & Island Tours
Boat & jetski rentals, island & state park tours in Islamorada from Robbie’s Marina.
Key West
Salty Bottom Boats
Salty Bottom Boat — private custom charters in Key West for sandbar parties, sunset cruises & island adventures.
Key West
Key West Coastal Charters
Set sail with Key West Coastal Charters and discover Key West’s famous sandbars on private charters full of snorkeling, dolphin-watching, nature, fishing & more.
Islamorada
Sundance Watersports
Explore stunning Florida Keys snorkeling, SNUBA, and sunset cruises with Sundance Watersports!
The Lower Keys
Snapshot Charters
Family-friendly Snapshot Charters offers unforgettable reef to swordfish fishing trips!
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
Living Like Larry Charters
Private boat charters in the Florida Keys for unforgettable ocean adventures.
Islamorada
Pelagic Raptors Charters
Cast lines with Captain Mike on Pelagic Raptors fishing charters
Marathon
Keys Jet Ski & Boat Rentals
High-octane jet ski rentals and guided water adventures in the Florida Keys.
Islamorada
Blackbeard Private Charters
Blackbeard Private Charters offers personalized boat excursions in the Florida Keys, including trips to the Islamorada Sandbar, snorkeling at Alligator Reef, sightseeing, and sunset cruises.
