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
After Hours Yacht
Private yacht charters in Key West for unforgettable sunset cruises and day trips.
Islamorada
Lightly Salted Charters
Private Islamorada boat tours: snorkel, sandbar, fishing—book your adventure.
Key West
Reel Paradise Charters
Experience unforgettable days on the water in the Florida Keys with private and shared charters from Key West.
Islamorada
Anchors Away Boat Rentals and Tours
Anchors Away Boat Rentals & Tours offers a diverse fleet of over 30 boats, including center consoles, deck boats, and pontoons, available for flexible rentals ranging from 2-hour to monthly durations, with GPS-equipped vessels and optional add-ons like snorkeling gear and GoPro cameras.
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
Wild Dolphin Tours
Wild Dolphin Tours — intimate dolphin-watching and snorkeling excursions in Islamorada where wild pods, reef adventures and island calm meet.
Key West
Florida Keys Flight Academy Key West
Florida Keys Flight Academy — flight training and scenic tours in Marathon, where aspiring pilots and adventure seekers soar over the stunning Florida Keys.
Key Largo
Morning Star Sailing Charters
Morning Star Sailing Charters offers personalized sailing experiences in the Florida Keys, including captained and bareboat charters, sunset cruises, and snorkeling tours.
Marathon
Sailing Catamaran Sirius - Ocean Sailing Inc
Sail the Florida Keys on the luxurious 36ft catamaran "Sirius" for unforgettable sunsets.
Key Largo
Key Largo Princess Glass Bottom Boat
Glass-bottom cruises over Molasses Reef—see the reef without getting wet.
Islamorada
KeyZ Charters
Explore the Florida Keys with KeyZ Charters—unique boat tours, snorkeling, and sunset cruises!
Islamorada
Forever Young Charter Company
Private dive, snorkel, spearfishing & fishing charters in the Florida Keys.
Key West
Second Generation Fishing Charters
We Fish Key West — your local charter partner for top offshore, reef, and backcountry fishing adventures.
Marathon
Nautica Watersports
Thrilling jet ski adventures and serene sunset rides in Marathon, Florida.
