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
Islamorada Turtle Tours
Sandbar trips, snorkeling, sunset cruises & private charters in Islamorada.
Marathon
Custom Cat Charters
Custom Cat Charters offers tailored private boat trips for fishing, sightseeing, and special events in the Florida Keys.
Marathon
Island Girls Excursions
Island Girls Excursions — premier boat tours and sandbar adventures in Marathon, Florida Keys, offering unforgettable sunset cruises and private island experiences.
Key Largo
Saltwater Cowboy Charterz
Experience unforgettable fishing and snorkeling adventures in Key Largo with Saltwater Cowboy Charterz.
Key West
Cora Beth Fishing
Cora Beth Fishing offers personalized, limited-load party boat and private fishing charters from Key West Bight Marina.
Marathon
Two Conchs Fishing Charters
A family-run charter fleet led by Capt. Jack Carlson, offering 20+ boats across The Florida Keys.
Key West
Up The Keys Tours
Up The Keys — immersive land-based eco-tours through the Florida Keys with expert local guides and scenic drives along the Overseas Highway.
Marathon
Crazy Banana Charter
Premier private fishing charters and scenic sunset cruises in Marathon and the Florida Keys — target mahi, tuna, wahoo and more with expert captains.
Islamorada
Wild Dolphin Tours
Wild Dolphin Tours — intimate dolphin-watching and snorkeling excursions in Islamorada where wild pods, reef adventures and island calm meet.
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.
Key West
Screaming Lines Adventures
Four generations of Estenoz heritage leading sportfishing adventures in Key West’s waters.
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
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.
Key West
FishMonster & IslandJane Charters
Key West’s premier fishing and adventure charters, offering everything from party boat fishing to private eco-tours and sunset sails.
Key West
Yankee Freedom Dry Tortugas Ferry
Dry Tortugas National Park — remote Florida Keys paradise 70 miles west of Key West featuring historic Fort Jefferson, turquoise water, pristine beaches and world-class snorkeling.
