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
Fury Water Adventures
Catamarans, parasails, jet skis and a glass bottom boat, running from several docks around Key West including the Historic Seaport and Opal Key. They also rent the golf carts and bikes for the part of the trip that happens on land.
Key Largo
Key Largo Tiki Tours
Float, sip & unwind—tiki cruises and private charters in Key Largo’s waters.
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 Ghost And Mysteries Tour
Guided walking tours of Key West’s haunted side, full of local lore, ghosts, and history—90 minutes of spooky fun whether you believe in the paranormal or not.
Key Largo
Pirate's Choice Sailing Vessel
Sail Key Largo’s pirate ship for sunset & snorkel adventures
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
CN-it Adventures
CN-IT Adventures offers personalized boat excursions in Key West aboard a 26-foot Twin Vee, delivering custom eco-tours, snorkeling, and island hopping catered to your preferences and weather conditions.
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.
Key Largo
Amoray Dive Resort
Amoray Dive Resort: Dive into adventure and relax in stunning Key Largo bayside rooms.
Weddings Max
60
Meetings Max
60
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
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
The Water Traveler Vacations
The Water Traveler is your luxury guide to private boat charters, all-inclusive captained getaways, and bespoke waterfront events.
Key West
Bear Holeman Charters
Bear Holeman offers expert inshore and offshore fishing charters in Key West, with captains boasting over 20 years of experience and ready-to-use gear for families, solo anglers, and seasoned fishers.
Marathon
Sailing Catamaran Sirius - Ocean Sailing Inc
Sail the Florida Keys on the luxurious 36ft catamaran "Sirius" for unforgettable sunsets.
Islamorada
Forever Young Charter Company
Private dive, snorkel, spearfishing & fishing charters in the Florida Keys.
