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
CN-it Adventures
CN-IT Adventures offers personalized boat excursions in Key West aboard a 26-foot Twin Vee, delivering custom eco-tours, snorkeling, and island hopping catered to your preferences and weather conditions.
Islamorada
Islamorada Turtle Tours
Sandbar trips, snorkeling, sunset cruises & private charters in Islamorada.
Key West
Aloha Sailing Key West
Personalized sailing charters aboard a Fountaine Pajot catamaran, exploring the Florida Keys and Dry Tortugas.
Islamorada
Blackbeard Private Charters
Blackbeard Private Charters offers personalized boat excursions in the Florida Keys, including trips to the Islamorada Sandbar, snorkeling at Alligator Reef, sightseeing, and sunset cruises.
Islamorada
Bluewater Adventure
Bluewater Adventure – The Keys offers guided two-person catamaran tours in Islamorada, allowing guests to drive their own boat while exploring the scenic waterways of the Florida Keys.
Marathon
Custom Cat Charters
Custom Cat Charters offers tailored private boat trips for fishing, sightseeing, and special events in the Florida Keys.
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.
Key West
Key West Express
Key West Express — high‑speed ferry service from Fort Myers Beach and Marco Island to Key West for relaxing day trips or island adventures.
Key West
Argo Navis Key West Sailing Charters
Argo Navis is a 75-foot luxury catamaran offering intimate, all-inclusive sailing experiences in Key West, including sunset cruises, brunch sails, and private charters, with curated food and drink pairings.
Key Largo
Key Largo Parasail
USCG-certified parasail adventures: soar over Key Largo’s waters in style.
Key West
Green Turtle Charters
Private charters in Key West offering sandbar trips, snorkeling, eco-tours, and dolphin watching.
Key Largo
Kickin It In The Keys Charters
Experience Florida Keys fishing adventures with Captain Forrest.
Key West
Classic Harbor Line Key West
Sail Key West offers unforgettable sunset and specialty cruises aboard the elegant Schooner America 2.0.
Marathon
Nautica Watersports
Thrilling jet ski adventures and serene sunset rides in Marathon, Florida.
