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.
Filters
Islamorada
Sundance Watersports
Explore stunning Florida Keys snorkeling, SNUBA, and sunset cruises with Sundance Watersports!
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
Keys Seaplanes
Fly in style over Florida’s waters — Keys Seaplanes offers private amphibious charters and scenic flights across the Keys.
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.
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
Argo Navis Key West Sailing Charters
Argo Navis is a 75-foot luxury catamaran offering intimate, all-inclusive sailing experiences in Key West, including sunset cruises, brunch sails, and private charters, with curated food and drink pairings.
Key West
The Water Traveler Vacations
The Water Traveler is your luxury guide to private boat charters, all-inclusive captained getaways, and bespoke waterfront events.
Islamorada
Florida Keys Boat Rentals, Jetski & Island Tours
Boats, jet skis and the Lignumvitae ferry, all out of Robbie's Marina at mile marker 77.5 bayside. The ferry runs Friday through Sunday afternoons to an island you cannot otherwise reach without a boat.
Marathon
Custom Cat Charters
Custom Cat Charters offers tailored private boat trips for fishing, sightseeing, and special events in the Florida Keys.
Marathon
Z Flight Watersports | Marathon FL
Zip into the sky with Z-Flight Watersports: parasailing thrills await.
The Lower Keys
Sandbar Somewhere Charter
Sandbar Somewhere Charter, led by Captain Hoyt Watkins, offers relaxed inshore and backcountry fishing trips around Summerland Key and Big Pine Key.
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.
The Lower Keys
Livin' the Dream Charters
Livin' The Dream Charters is a laid-back, locally run outfit fishing, diving, and cruising the Lower Keys out of Parmer's Resort on Little Torch Key. Whether you want to chase mahi offshore, spearfish the reef, scoop up lobster, or just soak in a sandbar sunset, Capt. Ray and Leah shape the day around you.
Key Largo
Caribbean Watersports
Private charters, sails, and snorkeling adventures in the Florida Keys.
