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
Clearly Unique Charters
Clearly Unique Charters offers snorkeling, sandbar, and sunset boat tours in Islamorada aboard spacious powerboats designed for family fun and special events.
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.
Key Largo
Blue Water Adventures
Blue Water Adventures offers private fishing charters, snorkeling trips, and sunset cruises aboard a 32-foot Gamefisher, departing from Key Largo Fisheries Marina.
Key West
Fly-Key West Helicopter Tours
Soar above Key West in a helicopter tour — scenic, adventurous, unforgettable.
Key West
Classic Harbor Line Key West
Sail Key West offers unforgettable sunset and specialty cruises aboard the elegant Schooner America 2.0.
Key West
After Hours Yacht
Private yacht charters in Key West for unforgettable sunset cruises and day trips.
Key Largo
Caribbean Watersports
Private charters, sails, and snorkeling adventures in 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.
Marathon
Sweet E'Nuf Charters
Experience top fishing adventures in Marathon, FL with expert captains and unforgettable catches!
Islamorada
Latitude Charters
Private boat charters in the Upper Keys — sandbar trips, sunset cruises, snorkeling & special-occasion charters.
Islamorada
Reel Attack Charters
Reel Attack Charters — full-service fishing charters in Islamorada, where expert guides, big catches and unforgettable Florida Keys experiences converge.
Islamorada
Sundance Watersports
Explore stunning Florida Keys snorkeling, SNUBA, and sunset cruises with Sundance Watersports!
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
Sandy Bottom Charters
Sandy Bottom Charters offers personalized private boat charters in the Florida Keys for snorkeling, sandbar trips, and sunset cruises.
