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
Cruisin’ Tikis Key West
Cruisin’ Tikis Key West offers fun, BYOB tiki-bar boat cruises—including sunset sails, swim-stop excursions, and eco tours—aboard floating tiki bars navigated by USCG-certified captains.
Key West
Ghosts & Gravestones Tour Key West
Nighttime trolley tour revealing Key West’s haunted history, including eerie tales and historic sites.
Key Largo
Tropic Ocean Airways
Tropic Ocean Airways — seaplane and charter flight service across Florida & the Bahamas, where effortless skies meet elevated coast-to-coast travel.
Islamorada
Sandy Bottom Charters
Sandy Bottom Charters offers personalized private boat charters in the Florida Keys for snorkeling, sandbar trips, and sunset cruises.
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 Largo
Pirate's Choice Sailing Vessel
Sail Key Largo’s pirate ship for sunset & snorkel adventures
Islamorada
Florida Keys Food Tours
Guided culinary tours through Islamorada & Key Largo featuring local eateries, history, and culture.
Marathon
Solé Watersports
Explore stunning snorkeling, sandbar swims, and sunset cruises in Marathon, FL!
Islamorada
Islamorada Fishing Charters Florida Keys
Offshore and inshore sportfishing charters in Islamorada.
Islamorada
Z Flight Watersports | Islamorada FL
Soar with Z-Flight Watersports—book your unforgettable adventure today.
Key West
Tiki Boat Adventures Key West Sandbar Charters
Tiki Boat Adventures — private tiki-bar boat charters in Key West for sandbars, sunsets & island-style fun.
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 Largo
Key Largo Princess Glass Bottom Boat
Glass-bottom cruises over Molasses Reef—see the reef without getting wet.
Marathon
Salt Dance Boat Tours
Custom private boat excursions in Marathon with sandbar trips, snorkeling adventures, and sunset cruises on a pet-friendly deck boat for families and friends.
Key West
Air Key West
Air Key West offers private, on-demand charters from Key West International Airport, specializing in flights to Cuba, the Bahamas, and throughout Florida.
