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Rich retirees rub elbows here with those who work two and three jobs to be able to call Key West home. And not just because a myriad of artists from Jimmy Buffet to Judy Blume will make art inspired by the island’s evening end. For any cruises listed, Cruise Critic does not guarantee any specific rates or prices. You can catch all kinds of exotic fish in Key West’s tropical waters, so it’s no surprise that much of the local cuisine centers on fresh seafood.
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The artist lineup of country music favorites includes John Michael Montgomery, Deana Carter, The Bellamy Brothers, Neal McCoy and Lacy J. Dalton. This is your chance to meet and greet the country stars, join in on jam sessions and attend panel discussions. If you like to kick up your heels, you'll have plenty of opportunities for line dancing, Texas swing and two-stepping. The city famously appeals to all types of folks, and attracts artists, hipsters, foodies and beach bums along with cruise ships. Locals love to repeat the line about never knowing if the guy beside you at the bar in flip flops and a tank top is a millionaire or a former merchant marine -- or both.
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Cruise ships have been coming to Key West for half a century. Here are the big moments - Miami Herald
Cruise ships have been coming to Key West for half a century. Here are the big moments.
Posted: Sun, 03 Apr 2022 07:00:00 GMT [source]
If you're a little more country than rock 'n' roll, maybe a cruise with a country twang is the right vacation for you. In February, Norwegian Gem will host the ninth installment of the popular Outlaw Country Cruise. This Sixthman voyage will sail from Miami and stop in Nassau, Bahamas, and St. Thomas. Maybe one stop in Jamaica isn't enough, and reggae vibes are calling your name. Cruise from vibrant Miami to Key West for a day spent splashing around in the cerulean waters or exploring the lively downtown scene.
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Key West was also a home away from home for President Harry Truman, whose one-time respite from Washington, D.C., is the "Little White House," a museum by the waterfront. The 2025 lineup includes Kool & The Gang, Shalamar, Lisa Lisa, George McCrae, Boogie Wonder Band, Rose Royce and other classic disco acts. In addition to more than 40 live performances, entertainment will include dance and costume parties, theme nights, dance contests and game shows. Passengers will appreciate the opportunity to go behind the music as artists sit for intimate Q&A sessions, panel discussions and meet-and-greets. Embark on a relaxing journey along Florida’s coast and through its sun-drenched island chain on cruises from Miami to Key West.
When the workday ends (or a little before), stop in for a drink at Rick’s Bar or Sloppy Joe’s and find live music along the way. Pub crawls down Duval are famous here, giving travelers a true sense of how fun the Key West nightlife can be. When your cruise ship docks, seek out a cafe con leche and a slice of key lime pie immediately.
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Shop for hand-made hammocks with Mayan prints, painted ceramics, sculptures, and artisan tequila at the Mercado Municipal, a short ride from the cruise terminal. Jam out at sea to the greatest disco anthems as Ultimate Disco Cruise and Beyond returns for a fifth year in 2025. The six-night cruise is an immersive, nonstop music festival with legendary music acts performing and hosting events throughout Norwegian Pearl. The round-trip itinerary from Miami includes port stops in Cozumel and Costa Maya, Mexico. For blues and jazz fans, Sixthman also offers the Keeping the Blues Alive at Sea X cruise, which sails from Miami and stops in Harvest Caye, Belize, and Costa Maya, Mexico. Aboard Norwegian Gem, passengers will have access to ship amenities like pools and a casino in addition to special music events.
If you’re looking for art galleries and clothing boutiques, head to Duval Street. 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. In Nassau, you’ll find small-town charm and plenty of exciting things to do and see.
Day 4: Fun Day at Sea
But there are also a variety of other methods to see Key West, like the Old Town Trolley. You can also rent bikes or scooters to catch the Key West breeze while you explore. For a sightseeing tour you’ll never forget, take the Conch Tour Train, which has been showing tourists around town since 1958. 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. Stop in after your visit to the Hemingway House; the museum is just around the corner.
Keep an eye on your belongings while you're downing a rum drink or frosty brew, or while singing along with the whole bar to a Jimmy Buffett or Kenney Chesney classic. While federal agents were trying to stymie drug smugglers, Keys residents decried the roadblock as a tourism disaster as well as disrespectful to its people. But Key West's mayor and his supporters failed to sway a federal court in Miami to lift the roadblock. Soon after, he read a proclamation at Mallory Square declaring the Keys no longer a part of the U.S. and demanding $1 million in foreign aid.
Walk in the footsteps of famous Pulitzer Prize-winning author Ernest Hemingway, who lived at 907 Whitehead Street in Key West from 1931 to 1939. Come see where Hemingway wrote several critically-acclaimed short stories, plus catch sight of the six-toed cats roaming the grounds. 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.
Key West cruise ship passengers, who number some 820,000 a year among the island's 3 million visitors, disembark at Mallory Square, a Navy pier near the Westin Resort. But the island city is a breeze to explore by walking, bike, scooter or even pedicab. Famous residents have included Pulitzer Prize-winner Ernest Hemingway, whose home on Simonton Street is now a museum where six-toed cats roam the grounds, pool and living quarters.
Visit the historic home of Ernest Hemingway and the beautiful Butterfly and Nature Conservatory. Enjoy the comfort, relaxation, and world-class service that you get on each and every luxury cruise with Celebrity. The lineup of '70s rock legends includes Air Supply, Kansas, The Guess Who, Melissa Manchester, The Family Stone and Dire Straits Legacy. They'll be performing, hosting events and attending special meet-and-greets.
You don't need to be able to tell a Monet from a Renoir to dine in our two artful dining rooms, you just need to be hungry. You don't even need to be a critic to enjoy Dive-In Movies, where cinematic favorites are up on the big screen, poolside. In the hours leading up to dusk, head to Mallory Square and watch as it comes to life with acrobats, dancers and performers.
The 2025 edition aboard Carnival Cruise Line's Carnival Magic will start in Miami and include stops in St. Thomas and Half Moon Cay, the line's private island in the Bahamas. Note that these specialty music cruises sell out — often as soon as cabins are made available. You'll be notified if someone cancels, as well as be among the first to be alerted of on-sale dates for future sailings. Rocking and rolling is not how most people prefer their cruise ships.
While on cruises to Key West, Florida, you’ll find no shortage of souvenir shacks, roadside t-shirt vendors, and Florida-related memorabilia celebrating and embracing Key West’s quirkiness. Head to Duval Street for the majority of shops, independently-owned boutiques, and galleries in the city. Or shop at Mallory Square for interesting goods like sandal and surf shops or markets for seashells and sea sponges. Just the right amount of kitsch, Key West bursts with sunlight, boasts year-round tropical weather, and some of the clearest snorkeling and most preserved coral reef structures in the world.
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