Exploring the Charms of the Key West Cruise Port

Arriving in Key West by cruise ship is the perfect way to experience this lively island paradise. As the southernmost point in the continental United States, Key West boasts a unique culture, history, cuisine, and natural beauty. With its laid-back vibe, walking and biking-friendly streets, and endless options for entertainment, it’s no wonder Key West is a favorite port of call for Caribbean cruises.

Most major cruise lines like Royal Caribbean, Norwegian Cruise Line, and Holland America offer Key West as a port of call. Docking at the Key West Bight pier right off Mallory Square, cruise passengers can easily explore all the iconic attractions of Key West on foot or bike.

And with a huge range of restaurants, bars, museums, and shops located just steps from the pier, you’ll have no problem finding ways to soak up the island life.

From snapping a photo at the Southernmost Point buoy to sipping cocktails on Duval Street, a day spent in Key West offers the quintessential Florida Keys experience.

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Key West Cruise Ship Port Map

Arriving at the Key West Cruise Port

The Key West cruise port has three different piers: Mallory Square Pier, Outer Mole Pier, and Pier B.

Depending on your cruise ship’s capacity and specific itinerary, you’ll arrive at one of these piers.

Mallory Square Pier and Pier B are within walking distance of Old Town. If you dock at Outer Mole Pier, you will be trolleyed into Old Town.

Approaching Key West by cruise ship is an exciting experience. As your ship pulls into the narrow channel, you’ll get your first glimpse of Key West’s pastel conch houses and the blue-green waters surrounding the island.

The cruise port places you just steps away from all the action.

Once your ship docks, you’ll go through customs and immigration pre-clearance before disembarking. The process is usually quick and efficient. Just make sure you have your passport, customs forms, and cruise ID ready.

After clearing customs, you’ll exit right onto Mallory Square or Duval Street, depending on your pier. This puts the island’s top attractions and eateries immediately at your footsteps, allowing you to maximize your Key West vacation.

Getting Around Key West

Key West is a walkable cruise port. However, I visited from San Antonio, Texas, where I am used to warm weather. If you are not accustomed to warmer temperatures, you may be more comfortable with one of the convenient transportation options in Key West.

Either way, Key West visitors can easily explore all the sights and attractions from the cruise port in a day.

Conch Train vs. Old Town Trolley

Riding the Conch Tour Train or Old Town Trolley makes navigating Key West easy and fun. You can sit back, relax, and take in the island’s charm without worrying about driving or parking. They are a hassle-free way to hit all the highlights at your own leisure.

The main difference is that the trolley will take you around the island while the train stays in Old Town.

Also, these tours can be booked on shore or in advance and are the exact same tours offered on the cruise ships. 

Key West Bike and Golf Cart Rentals

Additionally, if you prefer a more hands-on approach to exploring the island, Key West offers an array of transportation rental options, which can be booked directly on the pier when you disembark.

Bike and golf cart rentals are popular for cruising the island at a relaxed pace.

You will see bikes everywhere in Key West!

The best way to see everything in a short amount of time is to take a guided bike tour of Key West. You’ll meet your guide at the end of the cruise ship pier. Not only will they take you to the Key West’s highlights, but they will also share interesting history with you. Plus, you will end with a slice of Key Lime Pie!

Golf carts are another common way to get around the island. They are easy to park and are street-legal in Key West. Drivers must have a valid license and follow the same laws as cars, but they are much easier to use on the island.

You can book a golf cart directly with a vendor when you disembark. A four-seat golf cart costs between $30 and $50 per hour, but the prices seem to be negotiable based on what I saw.

I don’t recommend renting a car in Key West because of the limited parking and the bustling streets. Plus, you’ll miss the charm of slow-paced exploration that a car would not provide.

Key West Cruise Port Things to Do

Mallory Square

The Key West cruise port is within walking distance of Mallory Square, a bustling plaza located alongside Key West Harbor. Mallory Square is filled with shops, restaurants, and street performers and is one of the most popular waterfront destinations in Key West.

In the evening, Mallory Square transforms into a lively open-air entertainment venue. You’ll find a vibrant mix of talented street performers, artists, jugglers, and musicians. Sunset Celebration takes place each evening at Mallory Square as visitors clap and cheer the famous Key West sunset.

Grab a drink and stroll around the square, taking in panoramic views of the harbor.

Mallory Square offers excellent shopping and dining options.

Browse through souvenir kiosks and local art galleries showcasing Key West treasures.

Refuel at a waterfront restaurant like Bistro 245, serving Caribbean classics and seafood.

With its festive atmosphere and harborfront location, Mallory Square is a highlight of the Key West cruise port experience.

Duval Street

Duval Street is located in the heart of Key West and serves as the island’s main street. This famous 1.25-mile stretch offers the city’s best shopping, restaurants, galleries, and nightlife.

Strolling down Duval Street, you’ll find a vibrant, pedestrian-friendly street lined with charming buildings housing boutique shops, famous restaurants, tropical bars, and popular attractions.

Duval Street comes alive at night with its legendary nightlife scene. There’s something for everyone with laidback beach bars, lively piano bars belting out singalong hits, dance clubs with DJs, drag queen cabaret shows, and more. Think New Orleans’ Bourbon Street!

Some popular spots for drinks include Irish Kevin’s, with its nightly entertainment, and Bourbon Street Pub, known for its drag shows and dance parties. Make sure to order Florida’s best margarita at Sloppy Joe’s, known to be Ernest Hemingway’s favorite bar in Key West.

During the day, Duval Street offers excellent shopping and dining. Browse the souvenir shops and art galleries or eat at one of the many excellent restaurants.

Whether you’re looking for shopping, drinking, dining, or people-watching, a stroll down festive Duval Street captures the spirit and charm of Key West.

Southernmost Point

Once you disembark, I recommend visiting Mallory Square and then walking down Duval Street toward Whitehead Street. Duval will dead end, and then you will turn right onto Whitehead to get to the Southernmost Point buoy.

The Southernmost Point is one of Key West’s most iconic landmarks. Located on the corner of South Street and Whitehead Street, this large concrete buoy proudly marks the southernmost point of the contiguous United States.

This brightly painted buoy is a hugely popular photo location. Tourists line up to get their pictures taken in front of the big red, yellow, blue, and black marker.

Be prepared to wait your turn if you want that quintessential “southernmost point in the continental US” photo.

The landmark makes for a great photo backdrop, with the words “Southernmost Point Continental U.S.A.” painted on its side. It’s a fun way to document your Key West travels and prove you made it to the very bottom of the Sunshine State.

Key West Museums

Surprisingly, there are quite a few museums showcasing the Key West’s rich history and culture. Many of the museums are among the most popular attractions in Key West.

If there is one you are dying to see, I would go there first before sightseeing since there were lines almost everywhere we went.

Ernest Hemingway’s House

The Ernest Hemingway Home & Museum was the home of the renowned author Ernest Hemingway in the 1930s. Hemingway lived and worked there for over ten years and completed some of his most famous works in Key West, including To Have and Have Not and For Whom the Bell Tolls.

Today, the Spanish colonial house built in 1851 is a designated National Historic Landmark.

Visitors can take a guided tour to see where the author lived and worked, view his typewriter and book collection, see the room where his wife Pauline painted, and walk through lush tropical gardens.

The grounds are also home to dozens of six-toed cats, descendants of Hemingway’s original pet cat, Snow White. Fans of the author and lovers of literature, writing, and history will appreciate exploring this glimpse into the daily life of one of America’s literary icons.

Key West Lighthouse & Museum

One of the most iconic landmarks in Key West is the Key West Lighthouse.

The Key West Lighthouse is a must-see attraction for history buffs and those seeking panoramic views. The current lighthouse, built in 1848, is the oldest lighthouse in South Florida and one of the oldest in Florida.

Originally, the lighthouse was an important beacon for ships entering the dangerous waters of the Florida Keys.

Today, the Key West Lighthouse Museum features exhibits on Key West’s maritime past history. Climb the 88 steps to the top balcony for sweeping views of Key West Harbor. The views are especially stunning at sunset when the skies erupt in color.

Snap photos from diverse angles around the tower’s balconies. The black-and-white spiral pattern creates an iconic nautical scene. End your visit with a stop in the gift shop, which sells lighthouse-themed souvenirs and keepsakes.

Truman Waterfront Park

Truman Park is a great waterfront park to visit during your cruise stop in Key West.

Located about a twenty-minute walk from the cruise port, this free public park provides lovely views out over the water.

You will find the U.S. Coast Guard Cutter Ingham Maritime Museum here. Walk aboard and take the excellently laid out self-guided tour with pre-recorded information.

The tour will take you about an hour. You can end by visiting the gift shop or having a drink on the deck overlooking the Key West Marina.

Besides the vessel, the park offers pleasant shaded areas with benches to sit and enjoy the scenery, clean bathrooms, and a play place for kids.

Truman Waterfront Park is a nice spot to relax after exploring the bustle of Key West.

Key West Museum of Art & History at the Custom House

You can’t miss the Key West Museum at the Custom House overlooking Mallory Square. This historic building is a great place to stop and learn about Key West, Ernest Hemingway, and enjoy the art displays.

Make sure you stop at the gift shop at the entrance. It may be small, but you will find many authentic Key West souvenirs.

Mel Fisher Maritime Museum

The Mel Fisher Maritime Museum is fascinating. It features artifacts from shipwrecks and treasures discovered by the famous shipwreck salvor Mel Fisher. For example, you can see artifacts like jewels and gold from the 1622 Spanish galleon Atocha. The museum also has interactive exhibits explaining the challenging process of shipwreck salvage.

Key West Shipwreck Museum

The Key West Shipwreck Museum is near Mallory Square and the cruise ship port. It’s a small but interesting museum that focuses on the way of life of shipwreck salvagers. You’ll definitely want to climb the tower for a great view.

Truman Little White House

The Harry S. Truman Little White House, where the former president stayed for working vacations, is the only Presidential museum in Florida. It is located near the Westin Hotel on Front Street.

The site was used by six presidents, and the museum is filled with artifacts and historical tidbits.

If the tour is too pricey for you, there are two free exhibits and a free self-guided garden tour. You should also visit the Presidential gift shop on the premises.

Key West Butterfly and Nature Conservatory

On your way from Mallory Square to the Southernmost Point, the Key West Butterfly and Nature Conservatory is on Duval. It showcases over 60 species of butterflies, colorful birds, and flowers. If you are traveling with kids or have a strong interest in nature, I recommend you stop to enjoy the relaxing displays.

Shore Excursions

Dry Tortugas National Park is one of the top attractions to visit on a shore excursion from the Key West cruise port.

This 100-square-mile park is located 70 miles off Key West in the Gulf of Mexico and can only be accessed by boat or seaplane. The Yankee Freedom high speed catamaran takes visitors to the National Park but leaves at 7:30 AM, which may not work for all cruise passengers.

Dry Tortugas is almost entirely water with seven small islands. Most islands are undeveloped, but you can visit historic Fort Jefferson on Garden Key. Fort Jefferson is a huge 19th-century coastal fortress that makes for an incredibly unique and picturesque spot.

Key West Snorkeling

Key West snorkeling trips are also very popular excursions. The warm, clear waters surrounding the islands make it a prime area to spot tropical fish, rays, turtles, and coral reefs.

Most snorkeling excursions will provide all necessary gear and a knowledgeable guide. The coral formations and sea life you’ll encounter are truly world-class.

Key West Beach Access

On the south side of Key West, you’ll find Fort Zachary Taylor Historic State Park, home to Key West’s favorite beach.

The National Historic Monument dates back to the Civil War and houses the world’s largest collection of Civil War weaponry. Beyond its historical significance, Fort Taylor is the southernmost state park in the continental United States.

You have several ways to get to Fort Taylor, including walking, biking, or taking a bus. The walk will take around twenty-five minutes, whereas biking or taking a bus will take around ten.

The park’s entrance fee is less than $10, and at the Chickhee Hut Beach Rentals, you can rent beach chairs and umbrellas for around $40 for the day.

If you visit this beach, you will want to make sure you have water shoes since it is a coral beach with rocky sand.

Where to Eat and Drink in Key West

You will have no shortage of outstanding places to eat and drink in Key West. After exploring the island, refresh yourself at one of Key West’s top restaurants.

Key West Restaurants

We stumbled upon Blue Heaven on our way back to the cruise ship port from the Southernmost Point. Located in Bahama Village, it is quite a popular spot. You can expect to wait up to an hour for a table, but it is so worth it.

I recommend putting your name on the waitlist and then heading around the corner to see the Hemingway House & Museum. By the time your visit is complete, your table should be ready.

Dine outside in the restaurant’s tropical courtyard, surrounded by lush trees and flowers, live music, roosters, and cats.

Try their made-from-scratch pancakes, any of the fish dishes, or the Blue Heaven benedicts. Make sure to save room for the gigantic key lime pie!

For casual, open-air dining, check out Two Friends Patio Restaurant. Sit on the patio, feast on coastal favorites like the crab bisque or shrimp and lobster pasta, and sip an award-winning Bloody Mary. Don’t skip their homemade key lime pie for dessert.

Other highly recommended restaurants were the Key West Cuban Coffee Shop, Sunset Pier, Mangoes, Moondogs, and The Seaside Cafe at the Southernmost Mansion.

Key West Bars

You’ll have no trouble finding a drink in Key West, and it is perfectly ok to order a drink and take it with you as you explore. In fact, many of the bars along Duval Street have counter service.

You’ll definitely want to step inside Sloppy Joe’s Bar, a historic watering hole that Hemingway used to frequent, or grab a drink from the Southernmost Point Bar, just steps from the iconic buoy marker. It’s a great place to stop if you don’t want to wait for a picture at the original buoy.

Of course, being that my husband’s name is Kevin, we had to stop at Irish Kevin’s before making it back to the ship.

In Old Town, I recommend Hog’s Breath Saloon for its live music, raw bar, and a “Hog Snort” made of Bacardi Coco, pineapple juice and Blue Curacao.

These are just a few of the many bars in Key West, Let me know if you find a favorite!

Look for the Key West Cruise Port on Your Next Cruise Itinerary

Key West may be a small city, but its personality is larger than life. So the next time you consider a cruise itinerary, watch for Key West. The sights, sounds, and flavors make the Key West Florida cruise port a one-of-a-kind destination you’ll be happy to discover.

As you try the fresh seafood, indulge in a slice of key lime pie, and watch for those funky chickens, you’ll appreciate this slice of paradise.

With its laidback vibe and colorful cast of characters, Key West is a feast for the senses, serving up fun, adventure, and memories flavored with a dash of Florida quirkiness.

Come and discover this playful paradise for yourself, and let its infectious spirit captivate and delight you at every turn.

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