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
Six Fins Charters
Private luxury boat and jet ski charters in Key West — explore hidden reefs, sandbars, and dolphin playgrounds.
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
Bear Holeman Charters
Bear Holeman offers expert inshore and offshore fishing charters in Key West, with captains boasting over 20 years of experience and ready-to-use gear for families, solo anglers, and seasoned fishers.
Key Largo
Caribbean Watersports
Private charters, sails, and snorkeling adventures in the Florida Keys.
Islamorada
Lightly Salted Charters
Private Islamorada boat tours: snorkel, sandbar, fishing—book your adventure.
Key West
Florida Keys Air Tours LLC
Experience safe, scenic air tours and expert flight training in the Florida Keys—based at Key West International Airport.
Key West
Screaming Lines Adventures
Four generations of Estenoz heritage leading sportfishing adventures in Key West’s waters.
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
Classic Harbor Line Key West
Sail Key West offers unforgettable sunset and specialty cruises aboard the elegant Schooner America 2.0.
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
Key West Tiki Boat
Cruise Key West on a private tiki bar boat: sandbars, sunsets, paddleboards, lily pads, and your playlist—all aboard a fully decked out Tiki Boat for groups up to 12
Key West
Florida Keys Flight Academy Key West
Florida Keys Flight Academy — flight training and scenic tours in Marathon, where aspiring pilots and adventure seekers soar over the stunning Florida Keys.
Key West
Lost Reef Adventures
Lost Reef Adventures is a 5-Star PADI dive center in Key West offering daily scuba diving, snorkeling trips, certifications, sunset cruises, and private charters—all backed by 30 years of experience and full-service gear support.
Key West
Cora Beth Fishing
A 60 foot party boat out of C Dock at the Historic Seaport, running five hour reef trips from $75 with a limited load so nobody fishes elbow to elbow. They fillet your catch at the dock and a restaurant around the corner will cook it for you.
Key West
Aquaholics Charters
Aquaholics Charters offers private, customizable boat tours aboard a brand-new 2022 21' Tahoe, providing a stylish and comfortable way to explore the Florida Keys.
