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.
Filters
Key West
Key West Coastal Charters
Set sail with Key West Coastal Charters and discover Key West’s famous sandbars on private charters full of snorkeling, dolphin-watching, nature, fishing & more.
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
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.
Islamorada
Bluewater Adventure
Bluewater Adventure – The Keys offers guided two-person catamaran tours in Islamorada, allowing guests to drive their own boat while exploring the scenic waterways of the Florida Keys.
Key West
Dauntless Excursions
Dauntless Excursions offers private, customizable charters from Key West, featuring activities like lobstering, snorkeling, reef fishing, and sandbar hopping aboard the 32-foot Dauntless vessel.
Islamorada
Lightly Salted Charters
Private Islamorada boat tours: snorkel, sandbar, fishing—book your adventure.
Key Largo
Pirates Cove Watersports
Pirates Cove Watersports, located at Reefhouse Resort & Marina in Key Largo, is a top-rated watersports hub offering jet ski rentals, scuba diving & snorkeling, parasailing, eco-tours, sunset cruises, dolphin swims, fishing charters, and more—all under one roof.
Marathon
Two Conchs Fishing Charters
A family-run charter fleet led by Capt. Jack Carlson, offering 20+ boats across The Florida Keys.
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.
Marathon
Sweet E'Nuf Charters
Experience top fishing adventures in Marathon, FL with expert captains and unforgettable catches!
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
Forever Salty Charters LLC
Private snorkeling, sandbar, sunset & eco-tours from Islamorada.
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.
