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.
Key West
Fury Water Adventures
Fury Water Adventures offers the ultimate Key West experience, from thrilling water excursions to convenient land rentals
Islamorada
Latitude Charters
Private boat charters in the Upper Keys — sandbar trips, sunset cruises, snorkeling & special-occasion charters.
Islamorada
Florida Keys Watersports
Boat & jet ski rentals + tours exploring reefs, mangroves & sandbars in Islamorada.
Islamorada
Coral Keys Adventures
Coral Keys Adventures, founded by longtime Islamorada captain Rebekah Susa, offers immersive boat tours that blend snorkeling, history, and adventure at iconic sites like Alligator Lighthouse and Indian Key.
Key West
Cow Key Marina
Cow Key Marina is a full-service waterfront hub in Key West offering boat and jetski rentals, watersport tours, a waterfront restaurant, and even daily manatee sightings.
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
Salty Soul Charters
Custom private boat charters in Key West offering snorkeling, fishing, eco tours, and sunset cruises.
Marathon
Solé Watersports
Explore stunning snorkeling, sandbar swims, and sunset cruises in Marathon, FL!
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.
Key West
Fun in the Sun
Fun In The Sun Key West is the home of the original Key West sandbar charter, offering private captained boat charters, bareboat rentals, fishing trips, snorkeling, sunset cruises, boat bar crawls, golf cart rentals, and vacation rentals out of Stock Island Yacht Club with a 5-star TripAdvisor rating.
Key West
Sunset Watersports Key West
Sunset Watersports is Key West’s oldest and most trusted watersports provider, offering parasailing, snorkeling, jet ski tours, sunset dinner cruises, and more.
Islamorada
Spray Watersports
Spray Watersports is Islamorada's premier on-water adventure company offering guided jet ski tours, catboat tours, reef snorkeling, sandbar excursions, sunset cruises, and private tiki boat charters departing from Three Waters Resort & Marina with 1,000+ five-star reviews.
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.
