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
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.
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
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
Blue Horizon Charters
Blue Horizon Charters offers private boat adventures in Key West—ranging from sandbar escapes and snorkeling to sunset cruises—crafted by three lifelong friends passionate about island life and hospitality.
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
Skydive Key West
Experience tandem skydiving over the turquoise waters of the Keys at Skydive Key West.
Marathon
Island Warbirds - Aerial Tours & Gift Shop
Aviation gear & nostalgia—shop for pilot-apparel, model aircraft & warbird culture.
Key West
Reel Paradise Charters
Experience unforgettable days on the water in the Florida Keys with private and shared charters from Key West.
Marathon
Custom Cat Charters
Custom Cat Charters offers tailored private boat trips for fishing, sightseeing, and special events in the Florida Keys.
Key West
Cow Key Marina
Cow Key Marina is a full-service waterfront hub in Key West offering boat and jetski rentals, watersport tours, a waterfront restaurant, and even daily manatee sightings.
The Lower Keys
Rippin Line Charters
Explore Florida Keys waters with Captain Anthony—fishing, eco tours, and sunset cruises!
Islamorada
Reef Roamer Catamaran Snorkel Sail
Reef Roamer Catamaran Snorkel Sail is a family-owned, 44-foot sailing catamaran that has run reef trips from Old Conch Harbor in Tavernier since 2006. It offers morning and afternoon snorkel sails plus a sunset sail, with gear included and an easy staircase ladder that lets snorkelers of all ages get into the water.
Key West
Casual Monday Charters
Casual Monday Charters offers private, customizable boat excursions in Key West, featuring sandbar hopping, snorkeling, sunset cruises, and eco tours aboard a 25' Hydrasports center console.
Key West
Your Island Charter
Your Island Charter — private boat charters for sandbars, snorkeling, fishing and sunsets in the Florida Keys.
