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
Fury Water Adventures
Catamarans, parasails, jet skis and a glass bottom boat, running from several docks around Key West including the Historic Seaport and Opal Key. They also rent the golf carts and bikes for the part of the trip that happens on land.
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
Key West Sandbar Tours
Escape to hidden sandbars with Key West Sandbar Charters — private boat tours (small or large groups), crystal waters, sun, fun & photo-perfect views.
Key West
Making Memories Charters
Making Memories Charters — luxury private and custom boat charters, sandbar tours, snorkeling, island cruises, and sunset experiences in Key West.
Marathon
Solé Watersports
Explore stunning snorkeling, sandbar swims, and sunset cruises in Marathon, FL!
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 West
Reel Fresh Fishing
Reel Fresh Fishing — private fishing charters in Key West, where expert captains and top-tier gear deliver unforgettable deep-sea, reef and wreck experiences.
Key Largo
Pirates Cove Watersports
Pirates Cove Watersports, located at Reefhouse Resort & Marina in Key Largo, is a top-rated watersports hub offering jet ski rentals, scuba diving & snorkeling, parasailing, eco-tours, sunset cruises, dolphin swims, fishing charters, and more—all under one roof.
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.
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.
Key West
Salty Bottom Boats
Salty Bottom Boat — private custom charters in Key West for sandbar parties, sunset cruises & island adventures.
Marathon
Custom Cat Charters
Custom Cat Charters offers tailored private boat trips for fishing, sightseeing, and special events in the Florida Keys.
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
Key West Water Tours
Thrilling 2-hour guided jet ski tours exploring stunning Key West waters!
