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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Marathon
Hawks Cay Marina
Hawks Cay Marina on Duck Key offers wet slips, fuel, fishing charters and convenient access to the waters of the Middle Florida Keys.
Key West
Ghosts & Gravestones Tour Key West
Nighttime trolley tour revealing Key West’s haunted history, including eerie tales and historic sites.
Key West
Tiki Boat Adventures Key West Sandbar Charters
Tiki Boat Adventures — private tiki-bar boat charters in Key West for sandbars, sunsets & island-style fun.
Key West
Bear Holeman Charters
Bear Holeman offers expert inshore and offshore fishing charters in Key West, with captains boasting over 20 years of experience and ready-to-use gear for families, solo anglers, and seasoned fishers.
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 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
Wild Dolphin Tours
Wild Dolphin Tours — intimate dolphin-watching and snorkeling excursions in Islamorada where wild pods, reef adventures and island calm meet.
Key West
Old Town Trolley Tours Key West
Key West hop-on/hop-off trolley tour with narrated stops & perks.
The Lower Keys
Rippin Line Charters
Explore Florida Keys waters with Captain Anthony—fishing, eco tours, and sunset cruises!
Key West
Captain Hook's Dive Key West
A NOAA Blue Star dive operator running two trips a day out to the Vandenberg, Sand Key Lighthouse and the reefs off Key West, with a divemaster in the water on every dive. Snorkelers get their own departures and all the gear, and no experience is required.
Marathon
Two Conchs Fishing Charters
Capt. Jack Carlson has guided the Keys for more than 20 years, and all three of his sons run boats now too, which is how one family ends up with a fleet this size. More than 20 boats from 17 to 43 feet means the boat gets matched to your day, whether that is poling a flat for bonefish or a long run out to the Dry Tortugas.
Islamorada
KeyZ Charters
Explore the Florida Keys with KeyZ Charters—unique boat tours, snorkeling, and sunset cruises!
Key West
Green Turtle Charters
Private charters in Key West offering sandbar trips, snorkeling, eco-tours, and dolphin watching.
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.
