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
Islamorada
Bamboo Charters
Bamboo Charters, led by Captain Matt Bellinger, offers personalized fishing, snorkeling, sandbar, and sunset excursions aboard the "Chubby Mermaid," providing unforgettable experiences in the Florida Keys.
Islamorada
Forever Salty Charters LLC
Private snorkeling, sandbar, sunset & eco-tours from Islamorada.
Islamorada
A Family Fun Boat Tour Company
Load up your crew, your cooler and even your dog, then hand the wheel to a Coast Guard certified captain for a private day on the water out of Islamorada. Snorkel the reef, wade out on the sandbar, watch for dolphins in the mangroves or drift through sunset, and the day is yours to build.
Key West
Life On The Rocks Charters
Life on the Rocks Charters offers fun, customizable boat trips around Key West—sandbar hopping, snorkeling, sunset cruises, and more.
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.
Key West
Making Memories Charters
Making Memories Charters — luxury private and custom boat charters, sandbar tours, snorkeling, island cruises, and sunset experiences in Key West.
Key West
Key West Tiki Boat
Cruise Key West on a private tiki bar boat: sandbars, sunsets, paddleboards, lily pads, and your playlist—all aboard a fully decked out Tiki Boat for groups up to 12
Islamorada
Coastal Outfitters Sport Fishing Charters
Coastal Outfitters offers customized fishing charters and sunset cruises in Islamorada, delivering relaxed, captained outings tailored to your preferences.
Key Largo
Capt. Sterling's Everglades Tour
Captain Sterling's Everglades Eco-Tours offers personalized, small-group boat excursions through the Everglades National Park, Pennekamp Park, and Florida Bay, led by experienced guides passionate about wildlife conservation.
Key West
Florida Keys Air Tours LLC
Experience safe, scenic air tours and expert flight training in the Florida Keys—based at Key West International Airport.
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.
Key West
Old Town Trolley Tours Key West
Key West hop-on/hop-off trolley tour with narrated stops & perks.
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.
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.
