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
Key West Express
Key West Express — high‑speed ferry service from Fort Myers Beach and Marco Island to Key West for relaxing day trips or island adventures.
Key West
Rusty's Bucket Charters
Rusty's Bucket Charters offers private fishing trips, snorkeling, sunset cruises, and sandbar adventures aboard a 24' Sea Hunt center console. Led by Captain Russ, they provide a hands-on experience for up to six guests, with trips tailored to your preferences.
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
Sea Monkey Ocean Adventures
Exciting Key West boat tours and ocean adventures — snorkeling, sunset cruises & more.
Key West
Key West Conch Life Charters
Customize your perfect Key West adventure with fishing, snorkeling, and sunset cruises!
Key West
Aloha Sailing Key West
Personalized sailing charters aboard a Fountaine Pajot catamaran, exploring the Florida Keys and Dry Tortugas.
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 Largo
Caribbean Watersports
Private charters, sails, and snorkeling adventures in the Florida Keys.
Key West
Brightwild Adventures
Brightwild Adventures offers personalized boat excursions in Key West, including family and adult sandbar trips, sunset cruises, private charters, and golf cart rentals, all tailored to your preferences.
Marathon
Nautica Watersports
Thrilling jet ski adventures and serene sunset rides in Marathon, Florida.
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.
Islamorada
Blackbeard Private Charters
Blackbeard Private Charters offers personalized boat excursions in the Florida Keys, including trips to the Islamorada Sandbar, snorkeling at Alligator Reef, sightseeing, and sunset cruises.
Marathon
Marathon Snorkeling & Sunset Cruise
Explore stunning reefs, sandbars, and sunsets with Marathon's top snorkeling tours!
