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 Water Tours
Thrilling 2-hour guided jet ski tours exploring stunning Key West waters!
Tiki Boat Adventures Key West Sandbar Charters
Tiki Boat Adventures — private tiki-bar boat charters in Key West for sandbars, sunsets & island-style fun.
Six Fins Charters
Private luxury boat and jet ski charters in Key West — explore hidden reefs, sandbars, and dolphin playgrounds.
Two Conchs Fishing Charters
Capt. Jack Carlson has guided the Keys for more than 20 years, and all three of his sons run boats now too, which is how one family ends up with a fleet this size. More than 20 boats from 17 to 43 feet means the boat gets matched to your day, whether that is poling a flat for bonefish or a long run out to the Dry Tortugas.
Reef Quest Tours
ReefQuest Tours: Explore the vibrant reefs, wildlife, and sandbars of the Florida Keys on tailor-made, eco-educational boat adventures.
Off the Charts!
Off the Charts! offers personalized fishing charters, eco-tours, and sandbar excursions aboard a 32' Whitewater center console in Key West. Led by a captain with over 40 years of experience, they provide all necessary gear, safety equipment, and fishing licenses are included.
Green Turtle Charters
Private charters in Key West offering sandbar trips, snorkeling, eco-tours, and dolphin watching.
After Hours Yacht
Private yacht charters in Key West for unforgettable sunset cruises and day trips.
Florida Keys Air Tours LLC
Experience safe, scenic air tours and expert flight training in the Florida Keys—based at Key West International Airport.
Aloha Sailing Key West
A small, captain-run sailing charter out of Stock Island Marina Village, building each trip around what you actually want: backcountry anchorages, uninhabited islands, snorkeling in the national marine sanctuary. For the ambitious, a three day voyage out to Fort Jefferson in the Dry Tortugas.
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.
FishMonster & IslandJane Charters
A family run outfit fishing Key West since 2006, with boats at three Old Town docks: a 64 foot air conditioned catamaran running $85 half day party trips, a fleet of sportfishers, and a 52 foot sailing ketch for sunset charters and weddings. Fishing license and bait come included in the party boat fare.
Captain Stewys Charters
Captain Stewy's Charters offers private, personalized boat excursions in Key Largo, specializing in snorkeling trips, sandbar tours, eco tours, and sunset cruises for up to six guests.
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.