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
Old Town Trolley Tours Key West
Key West hop-on/hop-off trolley tour with narrated stops & perks.
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.
Key West
Dolphin Safari Charters Key West
Dolphin Safari Charters offers small-group dolphin watching, snorkeling and private boat charters departing from Stock Island near Key West.
Marathon
Island Warbirds - Aerial Tours & Gift Shop
Aviation gear & nostalgia—shop for pilot-apparel, model aircraft & warbird culture.
Islamorada
Robbie's of Islamorada
Robbie’s of Islamorada offers thrilling tarpon feeding, fishing, water sports, and vibrant local dining in the heart of the Florida Keys.
Key West
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.
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
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
Six Fins Charters
Private luxury boat and jet ski charters in Key West — explore hidden reefs, sandbars, and dolphin playgrounds.
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
Forever Salty Charters LLC
Private snorkeling, sandbar, sunset & eco-tours from Islamorada.
Key Largo
Eye Catcher Charters
Private fishing, snorkeling & sunset charters aboard a 30' Sea Hunt with Captain Bry.
Key West
Screaming Lines Adventures
Four generations of Estenoz heritage leading sportfishing adventures in Key West’s waters.
The Lower Keys
Longtab Charters
Luxury private charters from Summerland Key — fish, snorkel, dive, sandbars & sunset cruises aboard a 30′ Hydrocat.
Islamorada
Pelagic Raptors Charters
Cast lines with Captain Mike on Pelagic Raptors fishing charters
