Key West Cruise: Discover Cruises to Key West Florida

Tabs View Key West Cruises

View Key West Cruises

Key West Cruise Port Guide

On a cruise to Key West, you’ll discover a tiny tropical island at the very tip of the Florida Keys, packed with quirky shops, cool pubs, and historic houses. You’ll find everything here from kitsch to karaoke and crab claws to Cuban-style cigars.

There’s military history, the museum-house of literary legend Ernest Hemingway, and the daily festival scene of Mallory Square. And this is before you’ve spent time on one of the soft, white sand beaches, or browsed boho boutiques and galleries for local art and handmade jewelry. What’s more, Key West is enchantingly beautiful, with its tropical blooms and pastel-colored gingerbread houses. It’s easy to see why locals are so passionate about their little slice of paradise.

Cruises to Key West, Florida

View All Cruises to Key West

See Key West Cruises

View Cruises

View Cruises

Top Sights & Attractions for Cruises to Key West

Southernmost Point of the United States

On the corner of South and Whitehead streets, you’ll find a red, black, and yellow concrete buoy marking the southernmost point of the continental United States. It was put there by the City of Key West in 1983 and, unsurprisingly, has become a popular spot for selfies. Head several blocks north to the corner of Fleming and Whitehead, and there’s another marker for your collection: Mile 0 of Route 1. At 2,370 miles, it’s the longest highway in the United States.

Mallory Square

Mallory Square, a plaza facing the ocean, buzzes with life day and night. You’ll find bars and restaurants here, as well as souvenir and craft shops, art galleries, and the Key West Aquarium. Arrive from mid-afternoon as people start to gather before sunset to see fire-eaters, acrobats, fortune tellers, and buskers. Pick up conch fritters from the kiosk, buy some ice-cold beers, and take a ringside seat for people-watching.

Fort Zachary Taylor State Park

Fort Zachary Taylor, on the western tip of Key West, was built in 1845 and contains the world’s largest cache of Civil War armaments. It was used during the Civil War to defend the island from Confederate ships. Tour the fort to get a sense of life as a soldier here and admire cannons and gun ports. Then head to the pine-shaded beach for excellent snorkeling and the popular Cayo Hueso beach shack, where you can pick up wraps, burgers, and hot dogs, as well as ice-cold beer for lunch.

Top Things to Do in Key West

Explore Duval Street

Key West comes alive along the Old Town’s main strip, Duval Street, a long string of bars, drag shows, art studios, craft shops, and restaurants. Sit at one of the sidewalk cafés with a Cuban coffee during the day and later, drop into the iconic Sloppy Joe’s, which has stood here since 1933. Every historic building here tells a story. Captain Tony’s Saloon, for example, just off Duval on Greene Street, has served variously as a morgue, telegraph station, and cigar factory.

See the House Where Hemingway Lived

Visit the home of author Ernest Hemingway, who lived at 907 Whitehead Street from 1931 to 1939. This plantation-style home, built in 1851, is a National Historic Landmark. You can see the study and desk where Hemingway wrote some of his most famous novels, and gaze at hunting trophies and antiques. Some 60 cats roam the leafy grounds, many of them with six toes. They’re descendants of Hemingway’s original feline, Snow White, given to him by a ship’s captain.

Take a Break at Smathers Beach

Half a mile of soft, white sand, pretty Smathers is the longest beach on Key West, lined with palm trees. You can rent watersports gear and lounge chairs, or join a game of beach volleyball. Fuel up at Tropical Vibes Cones & Bowls, which does everything from acai bowls to Hawaiian shave ice. The water is warm and shallow, with a smattering of marine life and a sandbar just offshore. The beach is packed during Spring Break, but relatively quiet and family friendly for the rest of the year.

Top Food and Drink in Key West

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.

Culture & History of Key West

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 Cruise Port Facilities & Location

The Port of Key West comprises three docks: Pier B, Mallory Square, and the Navy Mole, or Outer Mole Pier. If your ship docks at the Navy Mole, there will be a shuttle trolley available to take you into town. You will most likely be docked at Pier B or Mallory Square, both of which are a short walk from many shops and attractions. Golf carts, Jeeps, and scooter rentals are available close to each dock.

Transportation in Key West

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.

Shopping Near the Key West Cruise Port

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.

Local Currency & Tipping Customs

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.