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
Robbie's of Islamorada
Robbie’s of Islamorada offers thrilling tarpon feeding, fishing, water sports, and vibrant local dining in the heart of the Florida Keys.
Key West
Dauntless Excursions
Dauntless Excursions offers private, customizable charters from Key West, featuring activities like lobstering, snorkeling, reef fishing, and sandbar hopping aboard the 32-foot Dauntless vessel.
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.
Marathon
SS Pops Two Conchs Island Tours
Explore stunning Florida Keys boat tours with Two Conchs Island Tours!
Marathon
Island Girl Charters
Experience unforgettable Florida Keys adventures with Island Girl Charters—fishing, snorkeling, and more!
Marathon
Two Conchs Fishing Charters
A family-run charter fleet led by Capt. Jack Carlson, offering 20+ boats across The Florida Keys.
Key West
Fun in the Sun
Fun In The Sun Key West is the home of the original Key West sandbar charter, offering private captained boat charters, bareboat rentals, fishing trips, snorkeling, sunset cruises, boat bar crawls, golf cart rentals, and vacation rentals out of Stock Island Yacht Club with a 5-star TripAdvisor rating.
Key West
Above & Below Fishing Adventures - Key West & Lower Keys Fishing Charters
Above & Below Fishing Adventures offers private, all-in-one Florida Keys charters—fishing, snorkeling, sunset cruises, spearfishing, lobster diving, and more—with full gear, Starlink Wi-Fi, and expert guides.
Key West
Lost Reef Adventures
Lost Reef Adventures is a 5-Star PADI dive center in Key West offering daily scuba diving, snorkeling trips, certifications, sunset cruises, and private charters—all backed by 30 years of experience and full-service gear support.
Key West
Sea Monkey Ocean Adventures
Exciting Key West boat tours and ocean adventures — snorkeling, sunset cruises & more.
Islamorada
Easy Livin' Charter Boat
Custom boat tours and fishing adventures with local legend Captain Augie in Islamorada.
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
Pirate's Choice Sailing Vessel
Sail Key Largo’s pirate ship for sunset & snorkel adventures
Islamorada
Reef Quest Tours
ReefQuest Tours: Explore the vibrant reefs, wildlife, and sandbars of the Florida Keys on tailor-made, eco-educational boat adventures.
