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.
Islamorada
Why Knot Boat Rentals & Charters
Why Knot Exclusive Rentals — custom boat rentals and captained charters in the Florida Keys for your perfect day on the water.
Marathon
Sweet E'Nuf Charters
Experience top fishing adventures in Marathon, FL with expert captains and unforgettable catches!
Islamorada
Glass Bottom Boats of Islamorada
See Florida Keys marine life through a clear-bottom boat tour.
Islamorada
Florida Keys Watersports
Boat & jet ski rentals + tours exploring reefs, mangroves & sandbars in Islamorada.
Islamorada
Lightly Salted Charters
Private Islamorada boat tours: snorkel, sandbar, fishing—book your adventure.
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
Morada Mermaid Adventures
The Morada Mermaid is a scenic charter boat experience in the Florida Keys offering sunset cruises, sandbar escapes, and island adventures from Marathon and Islamorada, FL.
Islamorada
Clearly Unique Charters
Clearly Unique Charters offers snorkeling, sandbar, and sunset boat tours in Islamorada aboard spacious powerboats designed for family fun and special events.
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.
Islamorada
Pelagic Raptors Charters
Cast lines with Captain Mike on Pelagic Raptors fishing charters
Islamorada
Reel Attack Charters
Reel Attack Charters — full-service fishing charters in Islamorada, where expert guides, big catches and unforgettable Florida Keys experiences converge.
Key West
Brightwild Adventures
Brightwild Adventures offers personalized boat excursions in Key West, including family and adult sandbar trips, sunset cruises, private charters, and golf cart rentals, all tailored to your preferences.
