Imagine a getaway where rich history meets breathtaking natural beauty, all set against the backdrop of sparkling turquoise waters. Key West offers the perfect destination for travelers seeking both relaxation and adventure. This guide to two days in Key West is designed to make your weekend in Key West unforgettable.
Day 1
Breakfast at Blue Heaven
Start your day at Blue Heaven, a quintessential breakfast spot beloved by locals and visitors alike. This open-air eatery is famous for its creative dishes like banana pancakes and Key West shrimp and grits, served in a setting brimming with island charm.
With chickens and cats roaming freely and live music often playing in the background, Blue Heaven offers more than just a meal — it’s a true Key West experience. Sip on freshly brewed coffee and enjoy the laid-back atmosphere that sets the tone for your adventures ahead.
See It All With Old Town Trolley
After breakfast, hop on the Old Town Trolley for an effortless way to explore Key West. This fully narrated tour offers a convenient way to visit the island’s top attractions while learning about its rich history and culture.
With stops at key landmarks like the Southernmost Point, Ernest Hemingway Home, and Mallory Square, the trolley allows you to explore at your own pace. Friendly and knowledgeable guides provide fascinating stories and insights, making it perfect for both first-time visitors and those rediscovering Key West.
Whether you’re planning a spontaneous trip or a meticulously organized weekend in Key West, the Old Town Trolley ensures you won’t miss a thing.
Explore the Southernmost Point
Make your way to the iconic Southernmost Point Buoy, a must-visit landmark in Key West. Get there early to avoid the crowds and snap your photo at this colorful marker, which stands as a symbol of Key West’s unique location — just 90 miles from Cuba.
Originally marked by a simple wooden sign, the buoy has a fascinating history. It has survived hurricanes, theft attempts and decades of tourism, standing strong as a representation of Key West’s resilience.
Nearby, explore Higgs Beach for a relaxing stroll or visit the Key West Butterfly & Nature Conservatory for a whimsical escape into a tropical habitat filled with fluttering butterflies.
Ernest Hemingway Home & Museum
Step into literary history with a visit to the Ernest Hemingway Home & Museum. Built in 1851, this stunning Spanish Colonial home served as the residence of Ernest Hemingway during one of his most productive writing periods.
Wander through the beautifully preserved rooms filled with original furniture, Hemingway’s typewriter, and personal belongings that bring his story to life. Outside, the lush gardens and famous six-toed cats, descendants of Hemingway’s own Snow White, add a playful touch to your visit.
Guided tours are available for those who want deeper insights into Hemingway’s life and works, making this attraction a can’t-miss for history buffs and literary enthusiasts.
Explore the Key West Butterfly & Nature Conservatory
For a peaceful afternoon escape, visit the Key West Butterfly & Nature Conservatory. This enchanting habitat immerses you in a tropical wonderland filled with colorful butterflies and exotic birds.
The climate-controlled glass structure recreates a rainforest environment, complete with cascading waterfalls and lush greenery. Here, you can observe over 60 species of butterflies as they flutter freely around you. Be sure to stop by the learning center to discover fascinating facts about the life cycle of these delicate creatures.
Don’t miss the resident flamingos, Rhett and Scarlett, who add an extra touch of charm to this serene retreat.
Enjoy a Scenic Lunch at Seaside Cafe at the Mansion
Take a break for lunch at Seaside Café at the Mansion, an idyllic spot where delicious food meets stunning ocean views. This beachfront eatery offers a menu filled with fresh, locally sourced ingredients. Popular choices include their signature lobster pizza or the refreshing mango chicken salad.
The laid-back atmosphere and attentive service make it an ideal spot to refuel and relax before continuing your journey through Key West.
Afternoon at Fort Zachary Taylor Historic State Park
Dive into history and natural beauty at Fort Zachary Taylor State Park, a National Historic Landmark with a picturesque beach. The park’s Civil War-era fort is home to the largest collection of seacoast cannons in the U.S. and offers a fascinating glimpse into the island’s past.
After exploring the fort, head to the beach for snorkeling in the crystal-clear waters or take a peaceful walk along the shaded nature trails. The park’s serene setting makes it a favorite for both history buffs and outdoor enthusiasts.
Evening Sunset Celebration at Mallory Square
The History of Mallory Square
Mallory Square has played a vital role in Key West’s history since the city’s formation in the early 1820s. Originally established as a base for the U.S. Navy’s West Indies Squadron under Commodore David Porter in 1823, its primary mission was to combat piracy, a significant issue in the region at the time. Later, during the Civil War, Mallory Square became a strategic location for both Union and Confederate forces, underscoring its importance in American military history.
By the mid-20th century, Mallory Square had become a symbol of Key West’s cultural heritage. Restoration efforts began in 1961, aiming to return the square to its 19th-century appearance. Today, it’s a must-visit destination for anyone spending two days in Key West. Known for its iconic Sunset Celebration and lively atmosphere, the square remains a cultural and historical cornerstone of the island.
Things To Do at Mallory Square
Sponge Market
Immerse yourself in the unique charm of the Sponge Market, where you’ll find an array of handcrafted souvenirs and local products. From decorative sea sponges to artisan jewelry, the market offers a glimpse into Key West’s rich maritime history while providing a vibrant shopping experience.
Sunset Celebration
No weekend in Key West is complete without experiencing the famous Sunset Celebration at Mallory Square. This nightly tradition draws visitors and locals alike to enjoy breathtaking views of the sun dipping below the horizon. The festivities include street performers, musicians, and artisans, creating a carnival-like atmosphere.
Art Galleries and Boutiques
Explore the nearby art galleries and boutiques offering works from local and international artists. From vibrant paintings to unique sculptures, these galleries showcase the creative energy of the island. Boutique shops in the area feature one-of-a-kind finds, including tropical apparel, home décor and locally inspired gifts.
Sweet Treats and Coffee Shops
Indulge your sweet tooth with a stop at one of the local dessert spots offering Key lime pie, cookies and fudge. For coffee lovers, cozy cafés serve rich brews and pastries, perfect for sipping as you take in the lively surroundings of Mallory Square.
Treasure Hunting in Local Shops
Take time to explore the shops offering a mix of nautical-themed goods, handcrafted items, and souvenirs. Each store adds its own touch to the Mallory Square experience, making it easy to find something memorable to bring home.
Dinner at Latitudes
Conclude your first day in Key West with an unforgettable dining experience at Latitudes, an upscale restaurant located on the serene Sunset Key. Accessible by a short ferry ride, this renowned eatery is celebrated for its stunning ocean views and elegantly prepared dishes. The menu highlights fresh, locally sourced ingredients, with options like lobster tail, yellowtail snapper and mouthwatering steaks.
The atmosphere at Latitudes is unmatched, with candlelit tables set against the backdrop of the gently lapping waves. Whether you’re enjoying a romantic evening or celebrating a special occasion, the setting ensures a perfect ending to your first day during your two days in Key West.
Day 2
Breakfast at Cuban Coffee Queen
Start the second day of your weekend in Key West with a visit to the beloved Cuban Coffee Queen. Known for its strong, flavorful coffee and authentic Cuban-inspired menu, this casual café is a favorite among both locals and visitors. Try their famous Cuban breakfast sandwich, made with fresh bread, eggs and ham, or enjoy a sweet guava pastry alongside a creamy café con leche.
The laid-back vibe and waterfront views make it a perfect spot to ease into your day. Grab your coffee to-go and take a peaceful stroll along the nearby marina, soaking in the early morning ambiance of Key West.
Visit the Harry S. Truman Little White House
The History of the Truman Little White House
The Harry S. Truman Little White House offers a fascinating journey into the life of one of America’s most impactful presidents. Built in 1890 as officer quarters for the U.S. Navy, the home later served as a winter retreat for President Truman during his presidency. From hosting key discussions about the Marshall Plan to drafting parts of the Truman Doctrine, the house became a backdrop for pivotal decisions in U.S. history.
As the only presidential museum in Florida, the house has been carefully restored to reflect its 1949 appearance, offering visitors a glimpse into Truman’s personal and professional life.
Things To Do at the Truman Little White House
Guided Tours
Take an immersive tour led by knowledgeable guides who bring Truman’s legacy to life. Walk through the very rooms where critical meetings took place and gain insights into the president’s time spent in Key West.
Explore Original Furnishings
Marvel at the original furniture and personal items preserved within the home. These artifacts provide a unique window into Truman’s lifestyle and tastes, from the dining room where he entertained to the bedroom he called his own.
Learn About Historic Events
Delve into the pivotal moments that occurred within the walls of the Truman Little White House. From the drafting of the Marshall Plan to strategic discussions during the Cold War, the house played host to key decisions that shaped global history. Guided tours provide fascinating details about Truman’s work in Key West, offering insight into how this peaceful retreat became a hub for high-stakes diplomacy and national strategy.
See the Presidential Limousine
Step outside to admire the beautifully preserved presidential limousine, an enduring symbol of mid-20th-century America. This iconic vehicle once transported President Truman and his distinguished guests around the island, and its sleek design and historical significance make it a must-see for visitors. Photographs and stories shared by the guides add an extra layer of context, bringing this piece of history to life.
Shopping on Duval Street
The History of Duval Street
Duval Street is not just a thoroughfare — it’s a vibrant centerpiece of Key West’s culture and history. Named after William Pope Duval, the first territorial governor of Florida, this iconic street has evolved from a humble road to a bustling destination. Over the decades, it has become synonymous with Key West’s unique charm, blending historical significance with modern attractions. From lively bars and restaurants to boutique shops and art galleries, Duval Street is the beating heart of Old Town Key West.
Its storied history and dynamic present make it a must-visit spot for anyone spending two days in Key West. Visitors from around the globe flock here to immerse themselves in the island’s lively atmosphere, enjoying everything from late-night entertainment to leisurely daytime shopping.
Bars To Explore on Duval Street
No weekend in Key West is complete without experiencing the famous nightlife along Duval Street. Here are three standout spots that capture the street’s spirited essence:
Sloppy Joe’s
A Key West institution since 1933, Sloppy Joe’s is a bar rich in history and fun. A favorite haunt of Ernest Hemingway, this lively spot offers a festive vibe with live music every night. Guests can enjoy signature cocktails like the Sloppy Joe Mojito while soaking in the energetic atmosphere. With its connection to one of America’s greatest authors and its ongoing popularity, this bar is a must-stop for both history buffs and partygoers alike.
Rick’s Bar
Rick’s Bar is not just a bar — it’s an experience. Spanning multiple levels, it includes a nightclub, a live music stage, and an outdoor tiki bar. Known for its cheap drinks and vibrant energy, Rick’s is a hub for those who want to dance the night away or relax with friends in an upbeat setting.
Irish Kevin’s
Irish Kevin’s is where entertainment meets interaction. Performers onstage frequently involve the audience, creating a uniquely engaging atmosphere. Known for its playful banter and lively music, Irish Kevin’s is a place where patrons are part of the show. It’s the perfect spot for letting loose, laughing and enjoying the dynamic energy that makes Duval Street unforgettable.
Duval Street Shops To Explore
For those who prefer shopping over sipping, Duval Street offers an array of unique stores and galleries that cater to every taste.
For the Art Enthusiast
Art lovers will find plenty to admire along Duval Street. Wyland Gallery showcases stunning marine-inspired works by renowned artist Wyland, while SeaSister Island Gallery features vibrant creations by local artisans, including jewelry, sculptures and paintings. If you’re looking for something more contemporary, Gallery on Greene and Alan S. Maltz Gallery offer cutting-edge photography and modern art exhibitions. For those who appreciate handcrafted pottery, KeyWestPottery combines tradition with creativity, making it a must-visit stop for collectors.
For the Fashionista
Fashion-forward visitors will appreciate the chic offerings at Indigo Boutique, known for its curated selection of clothing and accessories. The Green Pineapple blends stylish apparel with wellness items and home décor, creating a unique shopping experience. If bohemian vibes are more your style, Earthbound Trading Company offers an array of jewelry, crystals and boho-inspired clothing. For footwear needs, the Sandal Factory, a Key West staple since 1990, provides comfortable and stylish options perfect for exploring the island.
For Unique Souvenirs
No weekend in Key West is complete without bringing home a memento. There are many shops that provide an opportunity to take home a piece of Key West’s maritime history.
Indulge in a Dinner at Two Friends Patio Restaurant
After a day of shopping and exploring, unwind with a delicious meal at Two Friends Patio Restaurant, a local gem known for its friendly atmosphere and fresh seafood. The outdoor patio, adorned with twinkling lights, creates a magical setting perfect for enjoying the island breeze. Start your meal with their famous conch fritters, then dive into their “Two Friends” seafood platter, which showcases the best local catches.
Pair your dinner with a refreshing Key lime margarita, and don’t forget to save room for dessert — their Key lime pie is a crowd favorite. Whether you’re dining with friends or enjoying a romantic evening, Two Friends Patio Restaurant offers a quintessential Key West dining experience.
Ghosts & Gravestones Tour
As twilight falls, add a bit of thrill to your weekend in Key West with the Ghosts & Gravestones Tour. This guided experience immerses you in the island’s haunted history, whisking you away to Key West’s eeriest spots aboard the “Trolley of the Doomed.” Led by knowledgeable and costumed guides, this tour takes you through shadowed streets and historic locations while unraveling tales of famous spirits, chilling legends, and the island’s darker chapters. This ghostly tour introduces you to the city’s lesser-known side, blending fact with folklore and offering a memorable nighttime experience for anyone intrigued by history’s haunted tales. The Ghosts & Gravestones Tour is an excellent way to add some mystery to your two-day itinerary in Key West, leaving you with stories you’ll be talking about long after.
FAQs
What are the best activities for families in Key West?
Families will love exploring the Key West Butterfly & Nature Conservatory, visiting the interactive exhibits at the Key West Shipwreck Treasure Museum or relaxing on the beach at Fort Zachary Taylor State Park. The Old Town Trolley is another family-friendly option, offering a convenient and fun way to see the island.
What local dishes should I try in Key West?
Key West is known for its conch fritters, fresh seafood like grouper and Key West pink shrimp, and, of course, Key lime pie. For a true taste of the island, try the Cuban-inspired dishes at El Meson de Pepe or the decadent banana pancakes at Blue Heaven.
What are some must-see attractions in Key West?
A weekend in Key West wouldn’t be complete without visiting the Southernmost Point, the Ernest Hemingway Home, and Mallory Square’s Sunset Celebration. Don’t miss the shops and bars on Duval Street for a mix of history and nightlife.
How do I get around Key West?
Key West is easily navigable on foot or by bike. For those who prefer a guided experience, the Old Town Trolley offers a convenient way to explore the island while learning about its history.
What is the best way to spend two days in Key West?
Start with breakfast at Blue Heaven, visit iconic landmarks like the Hemingway Home and spend your evenings enjoying the Sunset Celebration at Mallory Square. Be sure to include shopping on Duval Street and catching a performance at the Key West Theater for a well-rounded itinerary.
