Key West Cruise Port: One Day Key West Itinerary

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This is your guide to your day ashore in Key West.



Where Do Cruise Ships Dock in Key West?

There are two main cruise docks in Key West. Both docks put you in the heart of Key West within a few steps. There's no need for buses, taxis, or other methods of transportation. When you exit your ship, head toward Mallory Square. This should be a 5-minute walk.

Mallory Square - Key West Florida

What to See in Key West

Explore Mallory Square

Mallory Square is a vibrant and iconic destination. Here's a comprehensive overview of visiting Mallory Square:

Location and Overview:

Mallory Square is situated at the northwest tip of Key West, right on the waterfront. It's a historic area that has become a gathering place for both locals and visitors to enjoy various activities, entertainment, shopping, and stunning views.

Mallory Square Sign - Key West Florida

Sunset Celebrations:

The most famous attraction at Mallory Square is the nightly Sunset Celebration. As the sun begins to set over the Gulf of Mexico, Mallory Square comes alive with performers, musicians, artists, and food vendors. This festive event draws crowds looking to enjoy the vibrant ambiance and breathtaking views as the sun sinks below the horizon. The Sunset Celebration is a key reason many people visit Mallory Square, creating a lively and festive atmosphere that's perfect for socializing, taking photos, and enjoying the arts.

Street Performers:

Mallory Square is renowned for its eclectic mix of street performers. You can expect to see magicians, fire jugglers, acrobats, musicians, and artists showcasing their talents. These performers contribute to the unique energy of the square, making it a dynamic and captivating place to explore.

Shopping and Art:

The area around Mallory Square is dotted with shops, galleries, and boutiques. You can find a wide range of items, from local crafts and artwork to souvenirs and clothing. The galleries often feature works by local artists, allowing you to take home a piece of Key West's creative spirit.

Key West Shell Warehouse Mallory Square Key West Florida

Don’t miss The Key West Shell Warehouse for an impressive collection of shells, shell art, and other “Conch Republic” merchandise.

Historical Significance:

Mallory Square has historical significance as it was named after Stephen Mallory, who was a United States Senator and Secretary of the Navy for the Confederate States during the American Civil War. The square has evolved over the years from a bustling maritime port to the vibrant hub it is today.

Key West Cruise Port - Mallory Square

The Key West Shipwreck Museum:

The Key West Shipwreck Museum is a small but fun museum dedicated to the maritime history of the area. Even if you’re only moderately interested there are plenty of free displays outside the museum to enjoy. The museum does a great job of making history come to life. Families with children would likely find this museum worth the time and money.

Dining and Cuisine:

Mallory Square and the surrounding area offer a wide range of dining options, from casual seafood shacks to upscale restaurants. You can enjoy fresh seafood, Caribbean flavors, and other culinary delights while taking in the scenic views.

Be sure to visit the stand selling conch fritters, a deep-fried local favorite.

Key West Cruise Port One Day Key West Itinerary - Key West Conch Fritter stand at Malory Square sunset

Getting There:

Mallory Square is easily accessible by walking from various points in Key West, as it's located near the heart of the city. If you're arriving on a cruise ship, it's within walking distance of the cruise port.

Tips for Visiting:

  • Arrive early for the Sunset Celebration to secure a good spot, especially if you're hoping to capture the perfect sunset photo.

  • Bring cash for tipping street performers and purchasing items from local vendors.

  • Consider exploring Mallory Square during the day to enjoy the shops, art galleries, and attractions without the crowds.

Mallory Square's unique blend of entertainment, art, culture, and natural beauty makes it a must-visit destination for anyone traveling to Key West, Florida. Whether you're captivated by the Sunset Celebration, the vibrant street performances, or the historic charm, Mallory Square offers an unforgettable experience.

You could easily spend the entire day exploring the attractions around Mallory Square.



Duval Street

Duval Street is the heart and soul of Key West, Florida. Known for its vibrant energy, diverse attractions, shopping, dining, and nightlife, it's a must-visit destination for anyone exploring the island. Our suggestion is to pick a side of the street and walk the 1.2-mile (2 km) street until the end, then repeat. Here's a comprehensive overview of visiting Duval Street:

Location and Overview:

Duval Street is the main thoroughfare running through the historic district of Key West. Stretching approximately 1.25 miles from the Gulf of Mexico to the Atlantic Ocean, Duval Street is a lively hub that offers a mix of cultural, entertainment, and recreational experiences.

Duval Street shops in Key West Florida

Attractions and Activities:

Duval Street is brimming with things to see and do, catering to a wide range of interests:

  • Shopping: Duval Street is lined with an eclectic mix of boutiques, galleries, and souvenir shops. You'll find everything from clothing and jewelry to local artwork and unique gifts.

    • Be sure to stop in for a slice of pie at Kermit's Key West Key Lime Shoppe. The key lime is king in Key West. Here you’ll find pretty much anything you can think of in the key lime flavor.

    • By now, you’ve likely seen your fair share of chickens running around the island. The Funky Chicken Store celebrates the chickens with amusing Key West chicken merchandise.

  • Dining: The street is a culinary paradise, featuring an array of restaurants, cafes, and eateries. From seafood shacks to upscale dining establishments, you can indulge in Caribbean flavors, fresh seafood, and international cuisine.

  • Historic Sites: Duval Street is home to historical landmarks, including the Ernest Hemingway Home and Museum, where the renowned author lived and wrote.

  • Museums: Explore attractions like the Key West Lighthouse and Keeper's Quarters Museum, which offer insights into the island's maritime history.

  • Art Galleries: Browse galleries featuring works by local artists, showcasing the vibrant art scene of Key West.

  • Live Entertainment: Enjoy live music, street performances, and a lively atmosphere that continues well into the evening.

  • Nightlife: Duval Street is famous for its nightlife, with bars, clubs, and pubs offering a range of entertainment options for night owls.

Kermit's Key Lime Shop in Key West Florida

Key West Historic Seaport:

At the northern end of Duval Street, you'll find the Key West Historic Seaport. This area is known for its marinas, sailing excursions, charter boats, and waterfront dining. It's a great place to explore nautical activities and enjoy fresh seafood while overlooking the water.

Annual Events and Festivals:

Duval Street plays host to various events and festivals throughout the year, including the Key West Fantasy Fest, which is a lively and extravagant Halloween celebration featuring elaborate costumes and parades.

Capt. Tony's Saloon sign in Key West Florida

Getting There:

Duval Street is centrally located in Key West, making it easily accessible by walking, biking, or taking a leisurely stroll from many points within the city. If you're arriving on a cruise, Duval Street is typically within walking distance from the cruise port.

Tips for Visiting:

  • Wear comfortable shoes as you'll likely do a lot of walking.

  • Stay hydrated, especially if you're exploring during the warmer months.

  • Be mindful of the crowds, especially during peak tourist seasons or events.

Whether you're seeking shopping, dining, entertainment, or a taste of local culture, Duval Street has something for everyone. Its vibrant and diverse offerings make it a quintessential Key West experience that captures the essence of the island's charm and uniqueness.

The most famous street on the island is home to loads of bars, dining, and shopping. Our suggestion is to pick a side of the street and walk the 1.2-mile (2 km) street until the end, then repeat.



A one-square block diversion from Duval Street will get you to The Hemingway Home and Museum.

The Hemingway Home and Museum

The Ernest Hemingway Home and Museum in Key West, Florida, is a historic landmark that offers visitors a glimpse into the life and legacy of the renowned American author, Ernest Hemingway. Here's everything you need to know about visiting The Hemingway Home and Museum:

Location and Overview:

The Hemingway Home and Museum is located at 907 Whitehead Street in Key West. The property includes a Spanish colonial-style house where Ernest Hemingway lived from 1931 to 1939. The museum is dedicated to preserving the history of Hemingway's time in Key West and showcasing his literary contributions.

House and Grounds:

The house itself is a beautiful structure with distinctive features, including a second-story wraparound veranda. The lush grounds are adorned with tropical gardens and a serene swimming pool. Cats also roam the property—many of them polydactyl (six-toed)—which is a nod to Hemingway's fondness for these unique feline companions.

secluded Key West Beach

Highlights and Attractions:

When you visit The Hemingway Home and Museum, you can expect to experience the following:

Guided Tours: Knowledgeable guides lead visitors through the home, providing insights into Hemingway's life, writing, and the historical context of the era.

Hemingway's Writing Studio: Hemingway's second-story writing studio, located above the carriage house, is a highlight. This is where he worked on some of his most famous works, including "To Have and Have Not" and "For Whom the Bell Tolls."

Personal Artifacts: The museum displays personal artifacts, memorabilia, and furnishings that belonged to Hemingway and his family. These items provide a deeper understanding of his life and interests.

Polydactyl Cats: The famous six-toed cats are a distinctive feature of the property. Hemingway was given a polydactyl cat by a ship's captain, and the descendants of that original cat still reside on the premises.

Gardens and Pool: The lush gardens and tranquil pool area provide a serene backdrop and offer visitors a chance to relax and enjoy the tropical ambiance.

Importaint Information:

  • Hours: The museum is open to the public daily from 9:00 AM to 5:00 PM.

  • Guided Tours: Guided tours are included in the admission price and last approximately 20-30 minutes.

  • Admission: $18 for adults, $7 for children aged 6-12, free for children 5 and under. Tickets are cash only and cannot be bought in advance or online.

  • Gift Shop: The museum has a gift shop offering books, souvenirs, and merchandise related to Hemingway and his works.

  • Photography: Photography is allowed on the grounds but not inside the house.

Tips for Visiting:

Comfortable Attire: Wear comfortable shoes and clothing suitable for walking and exploring the property.

Sun Protection: Key West can be sunny and warm, so bring sunscreen, a hat, and sunglasses.

Arrive Early: To avoid crowds, consider visiting earlier in the day.

Respect the Cats: The cats are a beloved part of the property, so treat them with care and respect.

Visiting The Hemingway Home and Museum is a chance to step back in time and immerse yourself in the world of one of America's literary icons. The museum provides a unique blend of history, literature, and tropical beauty, making it a must-visit destination for literature enthusiasts and history buffs alike.

Across the street, you’ll find the Key West Lighthouse.

Key West Lighthouse Key West Florida

Key West Lighthouse

The Key West Lighthouse is a historic landmark located in Key West, Florida. It offers visitors the opportunity to learn about the area's maritime history, enjoy panoramic views of the city and ocean, and explore a piece of the island's past. Here's a comprehensive guide to visiting the Key West Lighthouse:

Location and Overview:

The Key West Lighthouse is situated at 938 Whitehead Street in Old Town Key West. The lighthouse, constructed in 1847, served as a beacon for ships navigating the treacherous waters around the Florida Keys.

Historical Significance:

The lighthouse played a vital role in guiding ships through the coral reefs and shallow waters of the Florida Straits. It was built to replace an earlier lighthouse that had been destroyed by a hurricane. The light's design was unique for its time, featuring a central brick tower surrounded by a spiral staircase. The lighthouse keepers' quarters were located adjacent to the tower.

Attractions and Activities:

Lighthouse Tower: Climb the 88 steps to the top of the lighthouse tower for breathtaking panoramic views of Key West, the surrounding waters, and the historic district. The climb is rewarded with stunning vistas that showcase the island's beauty.

Museum and Exhibits: The lighthouse keeper's quarters have been converted into a museum that provides insights into the history of the lighthouse, its keepers, and maritime life in Key West. The exhibits include historical artifacts, photographs, and displays.

Gift Shop: The museum has a gift shop where you can purchase souvenirs, books, and items related to the lighthouse's history and maritime heritage.

Useful Information:

  • Hours: The lighthouse is open to the public daily from 9:30 AM to 4:30 PM.

  • Admission: $15.59 for adults, $11.50 for seniors,$7.50 for children aged 7-18, free for active military and children 6 and under.

  • Accessibility: The lighthouse tower climb involves ascending a narrow spiral staircase, which may not be suitable for those with mobility issues.

Tips for Visiting:

Comfortable Shoes: Wear comfortable footwear, as you'll be climbing the tower's spiral staircase.

Sun Protection: Key West can be sunny, so bring sunscreen, a hat, and sunglasses.

Camera: Don't forget your camera to capture the stunning views from the top of the lighthouse.

Historical Context: Take the time to read the exhibits and learn about the lighthouse's history to fully appreciate its significance.

Visiting the Key West Lighthouse offers a unique opportunity to learn about the region's maritime history while enjoying spectacular views from the top of the tower. The combination of history, culture, and scenery makes it a memorable stop for history enthusiasts, families, and anyone looking to delve into Key West's past.

Authentic Cuban Lunch

For lunch, take a diversion to El Siboney Restaurant at 900 Catherine St. The ten-minute walk off Duval is worth every step when you sink your teeth into their authentic Cuban cuisine. In addition to being delicious, you’ll also find that it is one of the best deals for food on the island.

Must-Try Dishes:

  • Ropa Vieja: A classic Cuban dish featuring shredded beef cooked with onions, peppers, and tomatoes. It's often served with rice and black beans.

  • Puerco Asado: Slow-roasted marinated pork that's tender and flavorful, usually served with rice, black beans, and plantains.

  • Cuban Sandwich: A pressed sandwich made with Cuban bread, roast pork, ham, Swiss cheese, pickles, and mustard.

  • Picadillo: Ground beef cooked with onions, bell peppers, olives, raisins, and spices, served with rice and sweet plantains.

Reservations: While El Siboney does not usually take reservations, arriving slightly earlier or later than peak dining hours might help you avoid a long wait. It is a popular spot for locals.

Sharing Dishes: The portions are often generous, so consider sharing dishes if you're not looking to have leftovers.

Prices: El Siboney offers good value for the quality and portion sizes of the food. The prices are reasonable and reflect the casual dining experience.

After lunch return to Duval and keep walking.

The Southernmost Point of the Continental U.S.A.

When you reach the end of Duval Street, take a final one-block diversion to the popular photo spot, The Southernmost Point of the Continental U.S.A.

Visiting the Southernmost Point of the Continental U.S.A. in Key West, Florida, is a popular and iconic experience. This historic marker represents the southernmost point of the contiguous United States and offers visitors a unique photo opportunity. Here's what you can expect when visiting this landmark:

The Southernmost Point marker is located at the corner of South Street and Whitehead Street. It's situated in a residential area near the shoreline.

The Southernmost Point marker is a brightly painted buoy-like structure that marks the southernmost point of the continental United States. The marker is a favorite photo spot for tourists and has become an iconic symbol of Key West.

Photo Opportunity: Visitors often stand in line to take photos with the marker as a backdrop. This is your best Instagram moment.

**Tips for Visiting:**

While the Southernmost Point marker itself is a relatively quick visit, it's a symbolic and memorable experience that many visitors enjoy.

Southernmost Point of the Continental USA marker in Key West Florida

From here you can choose to walk Duval Street back to Mallory Square or call a rideshare or taxi back to your starting point.

Other Things to See in Key West

If you have more time a visit to Fort Zachary Taylor Historic State Park is a great way to spend the day.

Fort Zachary Taylor Historic State Park in Key West Florida

Fort Zachary Taylor Historic State Park

Visiting Fort Zachary Taylor Historic State Park in Key West, Florida, offers a unique combination of history, outdoor recreation, and natural beauty. This state park is home to a historic Civil War-era fort, beautiful beaches, nature trails, and opportunities for relaxation and exploration.

  • Location: Fort Zachary Taylor Historic State Park is located at 601 Howard England Way. It's situated on the western edge of the island, offering stunning views of the Gulf of Mexico.

  • Admission: $2 per person or $8 per car

Historic Fort:

The park's main attraction is Fort Zachary Taylor, a historic military fort built in the mid-1800s to defend the Florida coastline. Visitors can explore the fort's well-preserved walls, artillery pieces, and interior rooms. Self-guided tours and informational signs provide insights into the fort's history and its role during the Civil War.

Beaches:

The park boasts two beautiful sandy beaches—the main beach and a smaller, more secluded beach. These beaches are known for their clear turquoise waters and are popular for swimming, sunbathing, and picnicking. The calm waters also make them suitable for snorkeling and other water activities.

Nature Trails:

Fort Zachary Taylor Historic State Park offers nature trails that wind through native vegetation and offer glimpses of the island's flora and fauna (mostly chicken and iguanas). The trails are easy to navigate and provide a peaceful escape from the bustle of downtown Key West.

Key West - Iguana

Picnic Areas:

The park provides shaded picnic areas equipped with grills and tables, making it an ideal spot for a leisurely picnic lunch or a barbecue with friends and family.

Snorkeling and Diving:

The park's clear waters make it a popular spot for snorkeling and diving. Underwater, you can explore coral formations, tropical fish, and other marine life. Snorkeling gear and equipment rentals are often available.

Truman Little White House

President Harry Truman was a huge fan of Key West and helped put it on the map while using it as his winter residence in the late 1940s and early 1950s. You can take a tour of the Truman Little White House for a deeper dive into the president’s life and legacy.

Location:

The Truman Little White House is located at 111 Front Street. It's situated in Old Town Key West, near the waterfront and within walking distance of other attractions.

Historical Significance:

The Little White House was originally built in 1890 as the naval station's command headquarters during the Spanish-American War. President Truman began using it as a retreat during his presidency in the late 1940s. The house has hosted numerous U.S. presidents and foreign dignitaries over the years. It's not only a historic residence but also a place where important decisions were made during Truman's presidency.

Guided Tours:

Visits to the Truman Little White House are conducted through guided tours. The knowledgeable guides provide insights into the history of the house, its role in presidential history, and the events that took place within its walls. You'll learn about Truman's time in Key West, the house's architectural features, and its significance in Cold War history.

Presidential History:

The Truman Little White House is often referred to as the "Winter White House" due to Truman's frequent visits during his presidency. The house's rooms are preserved to reflect the time period when Truman used it as a retreat, complete with original furnishings and decor.

Gardens and Grounds:

The property includes beautifully landscaped gardens that offer a serene and picturesque backdrop. Visitors can stroll through the gardens, admire the tropical vegetation, and enjoy the peaceful ambiance.

Key Information:

  • Hours: Guided tours from 9:30 am - 4:30 pm. Closed Sundays.

  • Admission: $22.95 per person for a one-hour guided tour.

Visiting the Truman Little White House offers a glimpse into both the personal life of a U.S. president and the historical context of the time. It's a must-visit for history enthusiasts, those interested in presidential history, and anyone looking to learn more about Key West's role in shaping the nation's history.

Key West Beach

In Closing

A visit to Key West from your cruise ship is a great way to get a taste of what Key West has to offer. Hopefully, you’ll fall in love with the island’s cham and decide to come back for a longer stay.

This map was created with Wanderlog, the best trip planner app on iOS and Android


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