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
Two Conchs Fishing Charters
A family-run charter fleet led by Capt. Jack Carlson, offering 20+ boats across The Florida Keys.
Islamorada
Pelagic Raptors Charters
Cast lines with Captain Mike on Pelagic Raptors fishing charters
Key West
SeaEO Luxury Boat Charters
SeaEO offers luxury private boat charters, rentals, and tours—servicing the Florida Keys and beyond. Experience personalized, high-end excursions aboard their ultra-luxury vessels, perfect for snorkeling, sandbars, dolphin safaris, special celebrations, or simply enjoying the sun and surf.
Key West
Above & Below Fishing Adventures - Key West & Lower Keys Fishing Charters
Above & Below Fishing Adventures offers private, all-in-one Florida Keys charters—fishing, snorkeling, sunset cruises, spearfishing, lobster diving, and more—with full gear, Starlink Wi-Fi, and expert guides.
Key West
Screaming Lines Adventures
Four generations of Estenoz heritage leading sportfishing adventures in Key West’s waters.
Marathon
Living Like Larry Charters
Private boat charters in the Florida Keys for unforgettable ocean adventures.
Key Largo
Pirate's Choice Sailing Vessel
Sail Key Largo’s pirate ship for sunset & snorkel adventures
Key West
Key West Ghost Tours: Southernmost Shadows and Ghosts
Discover Key West’s haunted history with a chilling walking ghost tour through cursed graveyards, eerie historic sites, and stories of restless spirits in the heart of Old Town.
Key West
Aloha Sailing Key West
Personalized sailing charters aboard a Fountaine Pajot catamaran, exploring the Florida Keys and Dry Tortugas.
Marathon
Duck Key Watersports
Duck Key Watersports offers unforgettable on-the-water adventures in the Florida Keys, from jet skis and paddleboards to kayaking and snorkeling.
Islamorada
Florida Keys Food Tours
Guided culinary tours through Islamorada & Key Largo featuring local eateries, history, and culture.
Key West
Sea Monkey Ocean Adventures
Exciting Key West boat tours and ocean adventures — snorkeling, sunset cruises & more.
Islamorada
Easy Livin' Charter Boat
Custom boat tours and fishing adventures with local legend Captain Augie in Islamorada.
Islamorada
Reel Attack Charters
Reel Attack Charters — full-service fishing charters in Islamorada, where expert guides, big catches and unforgettable Florida Keys experiences converge.
