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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Marathon
Sailing Catamaran Sirius - Ocean Sailing Inc
Sail the Florida Keys on the luxurious 36ft catamaran "Sirius" for unforgettable sunsets.
Key West
Fury Water Adventures
Fury Water Adventures offers the ultimate Key West experience, from thrilling water excursions to convenient land rentals
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
Wild Dolphin Tours
Wild Dolphin Tours — intimate dolphin-watching and snorkeling excursions in Islamorada where wild pods, reef adventures and island calm meet.
Islamorada
AquaBlue Adventures Sandbar Charter & Boat Tours
AquaBlue Adventures: Your go-to for expert-guided snorkeling, paddleboarding, and private eco-charters in the Florida Keys.
Key West
Key West Sandbar Tours
Escape to hidden sandbars with Key West Sandbar Charters — private boat tours (small or large groups), crystal waters, sun, fun & photo-perfect views.
Islamorada
A Family Fun Boat Tour Company
Family Fun Boat Tours offers private, kid-friendly boating adventures for up to 12 guests in the Upper Florida Keys—perfect for snorkeling, eco-tours, sandbar visits, sightseeing, or sunset cruises.
Islamorada
Forever Young Charter Company
Private dive, snorkel, spearfishing & fishing charters in the Florida Keys.
The Lower Keys
Longtab Charters
Luxury private charters from Summerland Key — fish, snorkel, dive, sandbars & sunset cruises aboard a 30′ Hydrocat.
Marathon
SS Pops Two Conchs Island Tours
Explore stunning Florida Keys boat tours with Two Conchs Island Tours!
Islamorada
Reef Roamer Catamaran Snorkel Sail
Catamaran snorkeling tours exploring Key Largo’s coral reefs.
Islamorada
Allergic to Land Charters
Discover Islamorada's waters with Captain Sue—snorkel, sunset, eco tours.
Key West
Reel Fresh Fishing
Reel Fresh Fishing — private fishing charters in Key West, where expert captains and top-tier gear deliver unforgettable deep-sea, reef and wreck experiences.
Islamorada
Islamorada Fishing Charters Florida Keys
Offshore and inshore sportfishing charters in Islamorada.
