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
Off the Charts!
Off the Charts! offers personalized fishing charters, eco-tours, and sandbar excursions aboard a 32' Whitewater center console in Key West. Led by a captain with over 40 years of experience, they provide all necessary gear, safety equipment, and fishing licenses are included.
Key West
Dolphin Safari Charters Key West
Dolphin Safari Charters offers small-group dolphin watching, snorkeling and private boat charters departing from Stock Island near Key West.
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
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.
Marathon
Z Flight Watersports | Marathon FL
Zip into the sky with Z-Flight Watersports: parasailing thrills await.
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.
Key Largo
Caribbean Watersports
Private charters, sails, and snorkeling adventures in the Florida Keys.
Key West
Aloha Sailing Key West
Personalized sailing charters aboard a Fountaine Pajot catamaran, exploring the Florida Keys and Dry Tortugas.
Key West
Fly-Key West Helicopter Tours
Soar above Key West in a helicopter tour — scenic, adventurous, unforgettable.
Islamorada
Bluewater Adventure
Bluewater Adventure – The Keys offers guided two-person catamaran tours in Islamorada, allowing guests to drive their own boat while exploring the scenic waterways of the Florida Keys.
Marathon
Marathon Snorkeling & Sunset Cruise
Explore stunning reefs, sandbars, and sunsets with Marathon's top snorkeling tours!
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
Sailing Catamaran Sirius - Ocean Sailing Inc
Sail the Florida Keys on the luxurious 36ft catamaran "Sirius" for unforgettable sunsets.
Islamorada
Islamorada Turtle Tours
Sandbar trips, snorkeling, sunset cruises & private charters in Islamorada.
