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
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 Largo
Caribbean Watersports
Private charters, sails, and snorkeling adventures in the Florida Keys.
Key West
Old Town Trolley Tours Key West
Key West hop-on/hop-off trolley tour with narrated stops & perks.
Key West
Captain Hook's Dive Key West
A NOAA Blue Star dive operator running two trips a day out to the Vandenberg, Sand Key Lighthouse and the reefs off Key West, with a divemaster in the water on every dive. Snorkelers get their own departures and all the gear, and no experience is required.
Islamorada
Seahorse Water Adventures
Explore reef, sandbars, and waves with jet skis, boats, and snorkeling adventures by Seahorse Water Adventures.
Marathon
Living Like Larry Charters
Private boat charters in the Florida Keys for unforgettable ocean adventures.
Key Largo
Blue Water Adventures
Blue Water Adventures offers private fishing charters, snorkeling trips, and sunset cruises aboard a 32-foot Gamefisher, departing from Key Largo Fisheries Marina.
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
Off the Charts!
Off the Charts! offers personalized fishing charters, eco-tours, and sandbar excursions aboard a 32' Whitewater center console in Key West. Led by a captain with over 40 years of experience, they provide all necessary gear, safety equipment, and fishing licenses are included.
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
Life On The Rocks Charters
Life on the Rocks Charters offers fun, customizable boat trips around Key West—sandbar hopping, snorkeling, sunset cruises, and more.
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.
