Top Key West Sightseeing Cruises

For the aquatic adventure of a lifetime, take this cruise to North America's only living coral barrier reef. No need to go scuba diving or snorkeling for this great view — from the deck of a glass-bottom catamaran boat, see more than 600 species of tropical fish, sharks, turtles, lobsters and crabs, plus colorful coral and a vast collection of other sea life. Upgrade to a sunset cruise to enjoy a glass of Champagne as the sun settles into the Gulf of Mexico.

Get ready for fun in the sun on this half-day sailing, kayaking and snorkeling adventure off the coast of Key West. Choose from a morning or afternoon excursion and set sail. Kayak through a maze of mangrove-canopied canals and streams, home to a tropical array of birds, rays, sharks, sport fish and more. Then jump into the water for a snorkeling session above a coral reef with 600 different species of marine life. Relax, feel the warm sea breeze and enjoy the day. Snacks, beer, wine, sodas and water included.

Leave behind the crowds of Key West and catch a quintessential Florida sunset while enjoying drinks on a sailboat. There is no better vantage point for watching the sunset over the water than from the water itself. And, while larger sunset cruises can get overcrowded, this small group experience ensures you have a spot at the rail when it comes time to capture photos of the setting sun.

Jam to crowd favorite beats by live musicians, eat, drink, and watch the sunset on this classic party cruise from Key West. Unlimited drinks and appetizers included.

Escape to the still waters off the coast of Key West on this small-group, sunset wine-tasting cruise. Enjoy the scenery and peaceful calm of a late afternoon sail on board a 65-foot schooner. Sample up to eight different wines and/or five different beers. Also included is a gourmet cheese buffet and other appetizers, like summer sausages, water crackers with brie, green apples with a honey drizzle and more. Then watch as the sun glistens and gently settles into the water, a perfect ending to a perfect cruise.

Set sail on a replica of the 1851 Schooner America on a cruise from Key West. See the top sights of the city, including Fort Zachary, Mallory Square, and Sand Key Lighthouse from a unique perspective. Your cruise is accompanied by complimentary hors d’oeuvres along with alcoholic and non-alcoholic beverages. Allow yourself to truly unwind as the sun sinks into the Atlantic Ocean.

Experience a slice of sailing history while soaking up fantastic Key West views on a cruise aboard the America 2.0, a replica of the schooner that won the very first America’s Cup. Relax on decks as your captain navigates the island coastline past landmarks like Fort Zachary Taylor and Sand Key Light Tower, and sip unlimited drinks from the full onboard bar.

Escape to Lake Country for a delightful day of wine tasting during this Kelowna wine tour. With complimentary hotel pick-up and drop-off in a comfortable and vehicle, you can enjoy a restful journey between each stop on your journey. Embark on a day of sipping and savoring at the Valley's finest wineries. Whether it's a romantic retreat or a corporate affair, this tour can be tailored to suit your desires.

Regular boat tours around Key West provide excellent views, but miss the most important view of all: the underwater world beneath the boat. This private glass-bottom boat tour provides the full, 360-degree experience of the waters around Key West. Exclusively for your group, this tour lets you create your own adventure, whether you want to snorkel the reef, explore an offshore island or simply relax on a sandbar.

Save money on top New York City attractions without investing in private transportation and a guide with this New York City sightseeing pass. Make your own way to the Statue of Liberty, Ellis Island, National September 11 Memorial and Museum, and Battery Park—your tickets are booked in ahead for hassle-free entry, and an audio guide is included to provide essential information about each location.

Watch the sun set and the moon rise off the coast of Key West on this private, 2-hour sunset cruise. Enjoy the scenery and peaceful calm of a late afternoon sail on board a private sailing vessel with a captain and mate. Stretch out and enjoy the breathtaking view. Then watch a legendary Key West sunset. Soft drinks are included. A cooler with ice is available to store any beverages brought on board.

Come experience the Crystal clear waters and sandbar island surrounding the Florida Keys. This tour can be completely tailored to whatever you have in mind. From drinking and relaxing on the sandbars to a full eco-tour through the Florida Keys marine sanctuary.