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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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
Adventures Key West
Adventures Key West is a full-service Key West experience booking company curated by local experts, offering everything from on-water adventures and private charters to golf cart and scooter rentals, cultural workshops, wellness experiences, and private event and wedding bookings throughout Key West.
Weddings Max
200
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
Key West Ghost And Mysteries Tour
Guided walking tours of Key West’s haunted side, full of local lore, ghosts, and history—90 minutes of spooky fun whether you believe in the paranormal or not.
Marathon
Manic Sportfishing
Manic Sportfishing is a top-rated Florida Keys fishing charter in Marathon offering private offshore, reef, and family-friendly fishing trips with experienced captains and premium boats.
Islamorada
AquaBlue Adventures Sandbar Charter & Boat Tours
AquaBlue Adventures: Your go-to for expert-guided snorkeling, paddleboarding, and private eco-charters in the Florida Keys.
Key West
Key West Seaplane Adventures
Soar over crystal waters and land on the Gulf—Key West’s premier seaplane tours to Dry Tortugas and beyond.
Islamorada
Sandy Bottom Charters
Sandy Bottom Charters offers personalized private boat charters in the Florida Keys for snorkeling, sandbar trips, and sunset cruises.
Key West
Classic Harbor Line Key West
Sail Key West offers unforgettable sunset and specialty cruises aboard the elegant Schooner America 2.0.
The Lower Keys
Longtab Charters
Luxury private charters from Summerland Key — fish, snorkel, dive, sandbars & sunset cruises aboard a 30′ Hydrocat.
Marathon
Sweet E'Nuf Charters
Experience top fishing adventures in Marathon, FL with expert captains and unforgettable catches!
Key West
After Hours Yacht
Private yacht charters in Key West for unforgettable sunset cruises and day trips.
Marathon
Sailing Catamaran Sirius - Ocean Sailing Inc
Sail the Florida Keys on the luxurious 36ft catamaran "Sirius" for unforgettable sunsets.
Islamorada
Morada Mermaid Adventures
The Morada Mermaid is a scenic charter boat experience in the Florida Keys offering sunset cruises, sandbar escapes, and island adventures from Marathon and Islamorada, FL.
