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Cruises to Key West, Florida are one of the most popular ways to see this walkable, immersive city. It’s easy to feel at home in Key West among swaying palms and small fishing boats glittering off the harbor. Once mostly cut off from the rest of the world, it has persevered through countless hurricanes.
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Credit cards like VISA and MasterCard are accepted most places as well. You can climb to the top of The Lighthouse and Keeper’s Quarters Museum for panoramic views of colorful beach homes, signature Florida greenery, and the waters of the Gulf of Mexico unfolding below you. Stop in after your visit to the Hemingway House; the museum is just around the corner. No Caribbean cruise is quite complete without experiencing Key West’s day-and-night bustle.
Southernmost Beach ResortArrow
Begin planning your U.S. cruise adventure with American Cruise Lines today. From the coast of Maine, to the mighty Mississippi and Pacific Northwest, our Free Cruise Guide provides detailed information about all of our more than 50 U.S. itinerary options. After breakfast on board, begin your journey home, reflecting upon the incredible experiences you’ve had and the wonderful new friends made.
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From Cayo Hueso to Key West:
Hop on the world-famous Conch Train to get a lesson in Key West history and hear local legends while touring Old Town and some of the island’s most iconic landmarks. Lowest pricing is based on our 3rd party pricing supplier and valid as of April 21st, 2024. Furthermore, Cruise Critic makes no guarantees for availability of prices advertised on our site. Key West isn’t as famous for its beaches as it is for other activities, but you can still lay down a beach towel and read a book at Smathers Beach. You’ll find this half-mile stretch of white sand is the largest public beach in Key West. If you have time, drive less than an hour northeast to Bahia Honda for the kind of Florida beach experience the state is famous for.
Afterwards, you’ll head to our private Beach Club experience in Bimini, Bahamas. And not just because a myriad of artists from Jimmy Buffet to Judy Blume will make art inspired by the island’s evening end. In Nassau, you’ll find small-town charm and plenty of exciting things to do and see.
Cruises to Key West, Florida
The park is also home to the 19th century Fort Jefferson, Fort Jefferson, was once used as a prison during the Civil War. Popular bars, T-shirt and souvenir shops and art galleries line both sides of the street and can be found from the 200 block to the end near Mallory Square. Although there is an open-container law in Key West prohibiting alcohol on public streets, it isn't largely enforced on visitors along the 100 and 200 blocks of Duval. Key West is an island, or Key, that is just two miles long by four miles wide, so all the essentials are near the docks -- bars, restaurants, shopping, scuba diving and beach-going. Mallory Square, on the waterfront near the docks, has restaurants, shops and public restrooms. For any cruises listed, Cruise Critic does not guarantee any specific rates or prices.
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We’re making waves from the Caribbean to the Med, the Adriatic to the Red, and everywhere in between across 4 continents. Join us on an unparalleled journey of relaxation and indulgence, and discover the things — and the people — that make each destination so special. Get a delicious taste of the modern romance of sailing that only a Virgin brand could pull off. From beach bonfires to private cabanas and floaty pool parties — all in a resort-like experience where you can actually let your salty hair down. Escape on a delightful Caribbean vacation on one of our cruises from Tampa to Key West.
Islands to Visit
This gallery has been updated with new information since its original publish date. During this time it almost never rains, and even if clouds do push through with some showers, they're gone that day. So we’re making both of those things happen.Wave goodbye to your routine and start planning an exclusively adult experience at sea. Enjoy your time sailing from Key West to Punta Gorda on board one of our brand new Coastal Cats. Admire the natural beauty that stretches out before you as you relax on your private balcony. Meet fellow travelers for lunch and attend an afternoon enrichment program presented by our onboard expert.
The island is home to stunning beaches and world-class golf courses, as well as beautiful parks to that are a paradise to those who relish the outdoors. After a day of adventure, dine at one of the elegant waterfront restaurants or peruse the artsy boutiques and designer outlets, before heading back to the ship. If you're looking for the perfect Mexican getaway with incredible diving and snorkeling, look no further than Cozumel. Visit the island’s more remote and wild east side to find breathtaking and secluded beaches like Punta Morena and Chen Rio.
Located at the southernmost tip of the United States, this cool little island hideaway is closer to Havana, Cuba, than it is to Miami. Visit two of Key West's best attractions, the Key West Shipwreck Treasures Museum and the Key West Aquarium. Developed by the world’s most-talked-about producers and artists, you have a ticket to all of our awe-inspiring shows. Browse, post, and stay connected with wifi — whenever you want, and wherever you are on the ship. Pre-upload your travel docs to the Virgin Voyages app, get Ready to Sail before leaving home, and make boarding a (sea)breeze in just a few minutes.
The result is a year-round paradise — except for hurricane season which typically starts in early June and ends in late November. Stay hydrated with still and sparkling water, non-pressed juices, sodas, teas and even drip coffee. There’s nothing more liberating than having the freedom of charting your own course. No pre-assigned seating, no fixed schedules, no limited options, no nonsense — just a shipload of opportunities to rejuvenate your body and transform your soul. Bask in Key West's laid-back yet wild vibes, knowing you can come and go as you please.
Tapas, tostones, plantains, and traditional Cuban sandwiches are all available here. For dessert, indulge in the coconut flan, then catch the sunset from the outdoor seating overlooking Mallory Square. Even in December, the forest and plants at this botanical garden in Key West retain their leaves and lush palms. The Garden describes themselves as “frost-free,” a benefit of the tropical climate. Bring the kids for an educational tour on the native plants, and don’t miss the butterfly garden. Damage from Hurricane Irma in 2017 affected the plant life, but passionate employees are working tirelessly to bring the garden back to peak fullness.
Head to this Florida State Park and National Historic Landmark for swimming, snorkeling, fishing, paddling, and more. Walk along the beach directly overlooking the warm waters of the Gulf of Mexico. Stop at nearby sandwich stand Cayo Hueso for a cold drink or a sandwich. At the corner of South Street and Whitehead Street in Key West is a concrete buoy marker of the southernmost point of the continental United States. Passengers on cruises that stop in Key West should see why this is one of the most photographed tourist attractions in the world. Every hotel review on this list has been written by a Condé Nast Traveler journalist who knows the destination and has visited that property.
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