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
Island Vibe Charters
Private Key West boat charters: sandbars, reefs & sunshine memories await.
Islamorada
Allergic to Land Charters
Discover Islamorada's waters with Captain Sue—snorkel, sunset, eco tours.
Key West
Green Turtle Charters
Private charters in Key West offering sandbar trips, snorkeling, eco-tours, and dolphin watching.
Key West
Florida Keys Air Tours LLC
Experience safe, scenic air tours and expert flight training in the Florida Keys—based at Key West International Airport.
Islamorada
Florida Keys Boat Rentals, Jetski & Island Tours
Boat & jetski rentals, island & state park tours in Islamorada from Robbie’s Marina.
Islamorada
A Family Fun Boat Tour Company
Family Fun Boat Tours offers private, kid-friendly boating adventures for up to 12 guests in the Upper Florida Keys—perfect for snorkeling, eco-tours, sandbar visits, sightseeing, or sunset cruises.
Islamorada
Coastal Outfitters Sport Fishing Charters
Coastal Outfitters offers customized fishing charters and sunset cruises in Islamorada, delivering relaxed, captained outings tailored to your preferences.
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
Latitude Charters
Private boat charters in the Upper Keys — sandbar trips, sunset cruises, snorkeling & special-occasion charters.
Marathon
Sailing Catamaran Sirius - Ocean Sailing Inc
Sail the Florida Keys on the luxurious 36ft catamaran "Sirius" for unforgettable sunsets.
Islamorada
Florida Keys Food Tours
Guided culinary tours through Islamorada & Key Largo featuring local eateries, history, and culture.
