Cruises to Key West, Florida

There are legendary dining spots and drinking dens around Mallory Square and restaurants all along Duval Street and in the side streets that radiate from here. You’ll find everything you need in the Old Town, from Hemingway’s old haunts to fine dining establishments.

Key West pink shrimp are found everywhere, sautéed, battered, fried, or in pasta sauces. On menus, you’ll see fresh snapper, grouper, mahi-mahi, and lionfish as ceviche, broiled, or fried. Seafood lovers will also enjoy stone crab claws with a mustard dipping sauce, spiny lobster, and conch chowder. Cuban specialties are rich in pork and beef, spiced and served with black beans, rice, and plantain chips. Then, of course, there’s the sweet, tangy, and irresistible Key lime pie.

Key West was originally inhabited by Calusa Native Americans. The explorer Juan Ponce de León was the first European to arrive, “discovering” the island in 1513. Key West became a Spanish territory, then called Cayo Hueso, or Bone Island. The British claimed ownership of Florida in the 18th century, expelling Native Americans and the Spanish from the area. Eventually, the United States claimed Key West in 1822.

Before the Overseas Highway was built in 1912 to connect the various Florida Keys, Key West itself was isolated from the rest of the world. Just 90 miles from Cuba, the island’s culture is heavily Cuban-influenced, particularly in its food and drink. Today, Key West’s economy is driven by tourism. The island is also known for its inclusive LGBTQ+-friendly community, its association with literary luminaries Ernest Hemingway and Judy Blume, and its gentle eccentricity.

Key West is only about four miles long and two miles wide, which means tackling the city on foot isn’t such a daunting idea. But there are plenty of other ways to see Key West, like the Old Town Trolley. This simple hop-on, hop-off trolley service runs all day. You can also rent bikes or scooters to catch the breeze while you explore. By-the-minute pedicabs are scattered throughout the town, while Uber and Lyft both operate here. For a sightseeing tour packed with narrative and local gossip, take the Conch Tour Train, which has been ferrying visitors around town since 1958.

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 sandals and surf gear. You’ll also find pottery, stylish resortwear, handmade jewelry, art prints, and items made from sea glass. And while you wouldn’t carry a slice of Key lime pie home with you, there are plenty of food items for sale infused with its flavor, from taffy to handmade cookies.

Key West’s official currency is the U.S. dollar (USD), and ATMs are widely available. Credit cards are accepted in most places as well. Tipping in Key West is similar to other U.S. destinations. Leave a 15-20% tip at restaurants and bars. Don’t forget to tip your barista for your morning café con leche, too. Carry a little bit of cash for your tour guide or taxi driver.

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