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
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.
Islamorada
Bamboo Charters
Bamboo Charters, led by Captain Matt Bellinger, offers personalized fishing, snorkeling, sandbar, and sunset excursions aboard the "Chubby Mermaid," providing unforgettable experiences in the Florida Keys.
Islamorada
Islamorada Turtle Tours
Sandbar trips, snorkeling, sunset cruises & private charters in Islamorada.
Marathon
Salty Pup Adventures
Explore unforgettable boat tours and adventures in Marathon, FL with Salty Pup Adventures!
Key Largo
Capt. Sterling's Everglades Tour
Captain Sterling's Everglades Eco-Tours offers personalized, small-group boat excursions through the Everglades National Park, Pennekamp Park, and Florida Bay, led by experienced guides passionate about wildlife conservation.
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 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.
Marathon
Fly Heli Florida Keys
Soar over the stunning Florida Keys with Fly Heli Tours for breathtaking island views!
Islamorada
Sundance Watersports
Explore stunning Florida Keys snorkeling, SNUBA, and sunset cruises with Sundance Watersports!
Marathon
Captain Hook’s Marina and Dive Center
A Blue Star dive shop and marina at mile marker 53 on Vaca Cut, running reef and wreck trips twice a day, plus snorkeling, sunset cruises, boat rentals and a bait and tackle counter. They will also put you on a coral nursery dive with Mote Marine Lab, which is not something most dive shops can offer.
Key West
Sebago Watersports
Top-rated Key West watersports & sailing tours — snorkeling, sunset sails, parasailing & more.
Key West
Second Generation Fishing Charters
We Fish Key West — your local charter partner for top offshore, reef, and backcountry fishing adventures.
Key Largo
Key Largo Tiki Tours
Float, sip & unwind—tiki cruises and private charters in Key Largo’s waters.
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
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