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.
Filters
Islamorada
MyKeys Tours of Islamorada
MyKeys Tours offers private snorkeling, sandbar, sunset & sightseeing charters aboard a 26′ SeaFox in Islamorada.
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
Key West Ghost And Mysteries Tour
Guided walking tours of Key West’s haunted side, full of local lore, ghosts, and history—90 minutes of spooky fun whether you believe in the paranormal or not.
Marathon
Sailing Catamaran Sirius - Ocean Sailing Inc
Sail the Florida Keys on the luxurious 36ft catamaran "Sirius" for unforgettable sunsets.
Islamorada
Pelagic Raptors Charters
Cast lines with Captain Mike on Pelagic Raptors fishing charters
Islamorada
Friend With A Boat Charters
Friend With A Boat Charters: Enjoy private, family-friendly boat tours out of Key Largo — snorkeling, sandbars, and BYOB fun on the water.
Marathon
Living Like Larry Charters
Private boat charters in the Florida Keys for unforgettable ocean adventures.
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
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 Largo
Tropic Ocean Airways
Tropic Ocean Airways — seaplane and charter flight service across Florida & the Bahamas, where effortless skies meet elevated coast-to-coast travel.
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 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.
Key West
Reel Fresh Fishing
Reel Fresh Fishing — private fishing charters in Key West, where expert captains and top-tier gear deliver unforgettable deep-sea, reef and wreck experiences.
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
Aloha Sailing Key West
Personalized sailing charters aboard a Fountaine Pajot catamaran, exploring the Florida Keys and Dry Tortugas.
