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
Reef Roamer Catamaran Snorkel Sail
Catamaran snorkeling tours exploring Key Largo’s coral reefs.
Key West
Air Key West
Air Key West offers private, on-demand charters from Key West International Airport, specializing in flights to Cuba, the Bahamas, and throughout Florida.
Islamorada
Deep Sea Scuba
Deep Sea Scuba & Snorkel in Islamorada offers top-quality personalized scuba diving, snorkeling, eco-tours, PADI training, and six-pack charters, all backed by over 25 years of safety-focused experience.
The Lower Keys
Rippin Line Charters
Explore Florida Keys waters with Captain Anthony—fishing, eco tours, and sunset cruises!
Key West
Island Vibe Charters
Private Key West boat charters: sandbars, reefs & sunshine memories await.
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 West
Blu Q Catamaran
Blu Q Catamaran offers unique, clothing-optional sailing experiences in Key West, featuring all-male day trips, sunset sails, and private charters aboard their 42-foot catamaran.
Key West
Key West Water Tours
Thrilling 2-hour guided jet ski tours exploring stunning Key West waters!
Marathon
Sweet E'Nuf Charters
Experience top fishing adventures in Marathon, FL with expert captains and unforgettable catches!
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.
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
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
Blue Horizon Charters
Blue Horizon Charters offers private boat adventures in Key West—ranging from sandbar escapes and snorkeling to sunset cruises—crafted by three lifelong friends passionate about island life and hospitality.
Islamorada
KeyZ Charters
Explore the Florida Keys with KeyZ Charters—unique boat tours, snorkeling, and sunset cruises!
Key West
Wall To Wall Fishing Charters
Wall To Wall Fishing Charters — premier private fishing and sandbar tours out of Key West for all ages and experience levels.
