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
Glass Bottom Boats of Islamorada
See Florida Keys marine life through a clear-bottom boat tour.
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
Pirate's Choice Sailing Vessel
Sail Key Largo’s pirate ship for sunset & snorkel adventures
Key West
Adventures Key West
Adventures Key West is a full-service Key West experience booking company curated by local experts, offering everything from on-water adventures and private charters to golf cart and scooter rentals, cultural workshops, wellness experiences, and private event and wedding bookings throughout Key West.
Weddings Max
200
Key West
Aloha Sailing Key West
Personalized sailing charters aboard a Fountaine Pajot catamaran, exploring the Florida Keys and Dry Tortugas.
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.
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.
Islamorada
Reel Attack Charters
Reel Attack Charters — full-service fishing charters in Islamorada, where expert guides, big catches and unforgettable Florida Keys experiences converge.
Islamorada
Deep Sea Scuba
Deep Sea Scuba & Snorkel in Islamorada offers top-quality personalized scuba diving, snorkeling, eco-tours, PADI training, and six-pack charters, all backed by over 25 years of safety-focused experience.
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.
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
Skydive Key West
Experience tandem skydiving over the turquoise waters of the Keys at Skydive Key West.
Marathon
Sailing Catamaran Sirius - Ocean Sailing Inc
Sail the Florida Keys on the luxurious 36ft catamaran "Sirius" for unforgettable sunsets.
Marathon
Adventure Boat Tours
Adventure Boat Tours takes visitors out from Marathon for snorkeling at Sombrero Reef and laid-back sunset eco-history cruises. Slip into the clear water over living coral, then watch the sky light up on the ride home through the Florida Keys.
