The best time to enjoy Key West is during the winter and early spring months, typically from December through April. The weather is mild and pleasant, with warm days and cooler evenings, making it ideal for outdoor activities like exploring historical landmarks, relaxing on the beaches and dining alfresco. This time of year also brings fewer chances of rain, ensuring your weekend plans stay on track. Keep in mind that this is the peak tourist season, so planning ahead and booking tours, accommodations and dining reservations early will help you make the most of your two days in Key West. If you’re looking for fewer crowds and better deals, late fall offers a great alternative, though temperatures may still be warmer.
Key West, with its sun-soaked landscapes, unique history and relaxed island vibes, is a destination like no other. Two days in Key West offers the perfect blend of adventure, culture and relaxation. This guide will help you maximize your visit, hitting all the must-see landmarks and ensuring you make the most of your time.
Day 1: Discovering History and Scenic Beauty
Day 1 is packed with some of the most iconic attractions Key West has to offer, allowing you to soak up the history, stunning coastal views and laid-back charm that make this island a beloved getaway spot.
Ride the Old Town Trolley
Kick off your two days in Key West with a ride on the Old Town Trolley, the perfect way to explore the island at your own pace while letting someone else do the driving. With convenient hop-on, hop-off stops, you can easily access Key West’s most treasured attractions without worrying about navigating traffic or parking. The trolley takes you through the heart of the island, stopping at landmarks like Mallory Square, the Hemingway House, and the Southernmost Point. Along the way, friendly and knowledgeable guides share captivating stories about Key West’s unique history, from its days as a bustling port to its reputation as a haven for pirates, artists and writers. The trolley’s open-air design offers scenic views and refreshing breezes, making it the most enjoyable way to see the island’s highlights in a short amount of time. For first-time visitors, Old Town Trolley Tours® provides both an entertaining overview and the flexibility to explore each stop at your leisure — ensuring you don’t miss a thing.
Breakfast at Blue Heaven
A morning in Key West wouldn’t be complete without a stop at Blue Heaven. Known for its whimsical outdoor seating, this beloved local gem combines charm with bold Caribbean-inspired flavors. Enjoy breakfast under the shade of tropical trees while roosters wander freely, adding to the laid-back island atmosphere. Their banana pancakes are a crowd-pleaser, light and fluffy with a hint of natural sweetness, while the savory eggs Benedict hits the spot for heartier appetites. Don’t leave without tasting their world-famous Key lime pie — a slice of tart, creamy perfection that pairs perfectly with a morning cup of coffee.
Strike a Pose at the Southernmost Point
Next, head to the Southernmost Point buoy, one of the most photographed landmarks in the United States. This colorful concrete buoy marks the southernmost tip of the continental U.S., sitting just 90 miles from Cuba. A quick stop here gives you the opportunity to grab an iconic photo while appreciating the geographical significance of Key West. Early mornings are ideal to beat the crowds and capture the best lighting for your snapshot. This short but memorable stop is an essential part of any two-days-in-Key-West itinerary.
Visit the Ernest Hemingway Home & Museum
No trip to Key West is complete without stepping into the legendary Ernest Hemingway Home & Museum. This beautifully preserved Spanish Colonial residence offers a fascinating look into the life of one of America’s greatest literary figures. Wander through Hemingway’s former writing studio, where he penned some of his most famous works, and learn about his time in Key West surrounded by inspiration and adventure. The lush gardens are home to the famous six-toed cats, descendants of Hemingway’s beloved pet Snow White. As you explore, the stories of Hemingway’s creative process and colorful life come alive, making this stop a highlight for history buffs and literature lovers alike.
Explore the Key West Butterfly & Nature Conservatory
Take a peaceful break and reconnect with nature at the Key West Butterfly & Nature Conservatory. This glass-enclosed paradise is teeming with hundreds of butterflies in a rainbow of colors, along with vibrant tropical birds fluttering freely throughout the lush landscape. The serene pathways wind through fragrant blooms and cascading waterfalls, creating a calming atmosphere ideal for relaxation. For families, couples or solo travelers, this stop is an enchanting experience that brings you closer to the natural beauty of Key West. It’s a wonderful addition to your two days in Key West, offering both tranquility and stunning photo opportunities.
Scenic Lunch at Seaside Café at the Mansion
When it’s time to refuel, head to Seaside Café at the Mansion for a laid-back waterfront lunch. Nestled by the ocean, this charming spot combines stunning coastal views with fresh, flavorful fare. Their signature lobster pizza, topped with buttery lobster and melted cheese, is a must-try and pairs perfectly with a refreshing tropical cocktail. The relaxed, open-air ambiance lets you enjoy the ocean breeze and clear blue skies while savoring a memorable meal. Whether you opt for seafood, a wood-fired pizza or a crisp salad, Seaside Café is the perfect midday stop to take in the beauty of Key West while indulging in its coastal flavors.
Relax at Fort Zachary Taylor State Park
After lunch, make your way to Fort Zachary Taylor State Park, a must-visit destination during your two days in Key West. This historic site blends natural beauty with significant history, making it a highlight for both explorers and beachgoers. Begin by strolling through the 19th-century fort, which played a pivotal role during the Civil War and remains one of the most intact examples of military architecture from that era. Informational markers throughout the grounds share fascinating stories of the fort’s construction and its strategic importance in defending the coastline.
Beyond its historical appeal, the park’s beach offers a tranquil retreat. Known for its clear waters and coral formations, the area is perfect for snorkeling. Beneath the surface, you’ll find tropical fish darting among the rocks, making this a favorite spot for underwater enthusiasts. If you prefer to stay dry, the park’s picnic tables and shady spots are ideal for a laid-back afternoon.
Witness the Sunset Celebration at Mallory Square
No Key West itinerary is complete without the Sunset Celebration at Mallory Square — a nightly event that captures the island’s lively energy and stunning natural beauty complete with street performers, artists, and vendors. Expect fire jugglers, musicians and magicians who captivate visitors of all ages, creating a festive, interactive experience.
The real draw, however, is the breathtaking sunset. Visitors gather along the waterfront to watch as the sky bursts into shades of gold, pink and purple, reflecting off the tranquil waters of the Gulf of Mexico. While you’re there, explore the artisan stalls offering handmade jewelry, art, and keepsakes — perfect for commemorating your two days in Key West.
Dinner at Latitudes
Conclude your evening with an upscale dining experience at Latitudes, located on Sunset Key, just a short ferry ride away from Key West. The journey to this exclusive waterfront restaurant sets the tone for a romantic and refined evening. Upon arrival, you’ll be met with sweeping views of the ocean and a peaceful, island ambiance that feels miles away from the bustle of Downtown Key West.
Latitudes is known for its exceptional seafood and locally inspired dishes. Start your meal with the Key West lobster bisque or fresh ceviche, followed by expertly prepared mains like the seared grouper or filet mignon. The restaurant’s focus on fresh, seasonal ingredients elevates every dish, offering flavors that reflect the region’s coastal heritage. Latitudes is the perfect way to cap off a day of sightseeing during your Key West weekend getaway.
Day 2: Iconic Attractions and Local Flavors
Day 2 of your two days in Key West offers even more opportunities to explore the island’s unique charm and culture. From must-see landmarks to delicious local fare, this day blends history, nature and culinary delights.
Breakfast at Cuban Coffee Queen
Kick off your morning at Cuban Coffee Queen, a local gem that’s earned its reputation for serving some of the best coffee and breakfast on the island. Known for its strong, authentic Cuban espresso, this small yet popular café delivers bold flavors that fuel a full day of activities. Pair your coffee with a hearty “Key Wester” breakfast sandwich or the classic Cuban toast, both of which highlight the café’s simple yet flavorful offerings.
As you enjoy your meal, take a moment to snap a photo in front of the colorful “Greetings from Key West” mural, a popular landmark that adds a splash of personality to the café’s setting. Cuban Coffee Queen is the perfect introduction to another round of Key West adventures on your Key West weekend getaway.
Tour the Harry S. Truman Little White House
Step into history at the Harry S. Truman Little White House, a significant landmark that offers a unique glimpse into the presidency of Harry S. Truman. Originally built in 1890 as a naval command headquarters, this charming Key West retreat evolved into a presidential sanctuary. President Truman spent 175 working days here, escaping the pressures of Washington while continuing to make crucial decisions that shaped postwar America.
During a guided tour, visitors can explore rooms preserved in their original condition, from the formal living spaces to Truman’s personal quarters. Original furnishings, photographs and artifacts provide an intimate look into both his personal and professional life. Visitors often enjoy learning about Truman’s daily routines here, including morning walks, poker games and casual meetings with cabinet members. The house’s peaceful surroundings make it easy to imagine the president finding both focus and relaxation here. A visit to the Truman Little White House offers history lovers an essential stop during their two days in Key West and provides an enriching look into America’s political past.
Explore the Key West Shipwreck Treasure Museum
Continue your journey into Key West’s storied past at the Key West Shipwreck Treasure Museum, where the island’s maritime history comes alive. Key West was once a bustling hub for shipwreck salvaging in the 1800s, as treacherous waters caused many vessels to run aground. At the museum, costumed actors vividly portray the lives of “wreckers” who braved danger to recover cargo, playing a vital role in the island’s economic success.
Inside, you’ll find carefully preserved artifacts recovered from actual shipwrecks, including tools, silver and other cargo that reveal the life and commerce of the era. The highlight of the museum is the climb to the top of the 65-foot lookout tower. Historically, this was where wreckers kept a watchful eye for distressed ships on the horizon. Today, the tower offers panoramic views of Key West’s waterfront and turquoise waters, providing a picture-perfect spot for visitors.
Lunch at El Meson de Pepe’s
Take a break from exploring and savor the flavors of Key West’s Cuban heritage at El Meson de Pepe’s. Located in the heart of Mallory Square, this lively restaurant has been a staple of the island for over three decades, serving authentic Cuban cuisine in a festive setting. Inside, you’ll find vibrant décor, colorful murals, and the rhythmic sounds of Latin music that add to the welcoming atmosphere.
The menu features timeless Cuban dishes, each crafted with bold, traditional flavors. Start your meal with crispy yucca frita or a refreshing mango salad. For a heartier option, try ropa vieja, a savory dish of shredded beef simmered with onions, peppers and tomatoes, or lechón asado, tender roast pork marinated in garlic and citrus. Pair your meal with a side of black beans and sweet plantains for the full experience. To cap off your lunch, sip on a classic Cuban espresso or enjoy a chilled mojito.
Dining at El Meson de Pepe’s is more than just a meal; it’s a celebration of Key West’s Cuban influence and community.
Discover the Charms of Duval Street
An afternoon on Duval Street is the perfect way to experience the colorful essence of Key West. Stretching from the Gulf of Mexico to the Atlantic Ocean, this lively street invites visitors to stroll through a mix of eclectic shops, historic bars and inviting cafés. Whether you’re enjoying a leisurely walk, hunting for treasures or savoring local drinks, Duval Street is a must-see stop during your two days in Key West.
Bars to Explore:
Sloppy Joe’s Bar: For a taste of history, visit Sloppy Joe’s Bar, a favorite haunt of Ernest Hemingway. With its welcoming vibe, live music, and classic cocktails, it’s an iconic stop.
The Original Margaritaville: Another can’t-miss spot is Margaritaville, where the breezy atmosphere and refreshing margaritas embody Key West’s laid-back spirit. Grab a seat, sip a drink and take in the tropical energy that makes these bars local favorites.
Duval Street Shops To Explore:
Shopping along Duval Street blends charm, craftsmanship and unique finds.
For the Fashionista: Boutiques like Vignette and Lilly Pulitzer feature resort-inspired clothing and accessories perfect for the island lifestyle. Browse light fabrics, stylish dresses and accessories designed to help you look your best while staying cool in Key West’s coastal climate.
For Unique Souvenirs: Pick up meaningful mementos at the Key West Sponge Market, where you’ll find natural sponges, candles and marine-inspired gifts. Local Color is another gem, showcasing handcrafted jewelry, colorful scarves and artisan treasures.
Experience Key West Nightlife at the Key West Theater
Housed in a beautifully restored 19th-century building, the Key West Theater is an intimate venue that offers a lineup of live performances ranging from energetic concerts to stand-up comedy and dramatic plays. The theater’s warm atmosphere, excellent acoustics, and engaging shows provide an ideal way to unwind after a day of exploring.
The diverse programming often includes local musicians and nationally recognized acts, making it easy to find something you’ll enjoy. Live music lovers can expect acoustic sets, blues and rock bands, while comedy fans will appreciate the intimate setting for a night of laughs. If you’re planning your two days in Key West, check the theater’s calendar in advance to catch a show that adds a fun and cultural twist to your evening plans.
Finish the Night on a Ghosts & Gravestones Tour
Wrap up your Key West weekend with a spine-tingling adventure with Ghosts & Gravestones. This popular nighttime tour brings Key West’s haunted history to life through chilling tales, eerie locations and atmospheric storytelling. Known for its rich history and ghostly legends, the island has earned its reputation as one of America’s most haunted destinations. Climb aboard the tour’s trolley and journey through dimly lit streets as your guide shares ghostly stories of long-departed residents and mysterious events.
The journey may include visits to haunted Old Town, historic buildings, and shadowy cemeteries, where the past seems to linger. Whether you’re fascinated by history or intrigued by the paranormal, the Ghosts & Gravestones Tour offers an unforgettable and atmospheric way to experience Key West after dark. Be sure to book ahead, as this chilling tour is one of the most popular nighttime activities for visitors exploring two days in Key West.
FAQs
Absolutely! Key West is a culinary haven, and you can’t spend two days in Key West without indulging in some signature dishes and local hot spots. Start with a slice of Key lime pie at Blue Heaven, a whimsical and iconic eatery known for its Caribbean-inspired cuisine. For seafood lovers, Latitudes on Sunset Key is a must-visit for its elegant dishes like fresh lobster tail and yellowtail snapper served with oceanfront views. If you prefer Cuban flavors, El Meson de Pepe’s offers traditional dishes like ropa vieja and Cuban sandwiches alongside vibrant, lively ambiance. Don’t miss trying conch fritters, a local favorite, or lobster pizza at Seaside Café at the Mansion.
Spending two days in Key West as a family offers countless activities that kids and adults alike will enjoy. Visit the Key West Butterfly & Nature Conservatory, where children can marvel at colorful butterflies, exotic birds and tropical plants. Stop by the Key West Aquarium to get up close with marine life, including stingrays and sea turtles, or take in the views from the top of the Key West Shipwreck Treasure Museum. Families will also love Fort Zachary Taylor State Park, where you can explore historical fort grounds, swim, snorkel and enjoy a picnic by the beach. For a unique evening experience, head to Mallory Square for the Sunset Celebration, featuring street performers, artisans and breathtaking views that the entire family will remember.
Key West is a small, walkable island, making it easy to get around during your two days in Key West. Walking is the best way to explore iconic streets like Duval Street and local landmarks like the Southernmost Point. If you prefer a quicker option, rent bicycles or electric golf carts, both of which are popular and fun ways to explore. The Old Town Trolley Tour is another fantastic option, providing a hop-on, hop-off experience that connects you to all of the island’s top attractions with ease. Additionally, taxis, ridesharing services, and pedicabs are readily available for short trips around town. For those staying further from the main attractions, renting a scooter offers a perfect balance of flexibility and island-style travel.
The perfect two days in Key West combines history, nature, food and local charm. Start Day 1 with an Old Town Trolley Tour to get acquainted with the island, followed by breakfast at Blue Heaven. Visit iconic stops like the Ernest Hemingway Home & Museum, the Southernmost Point, and the Key West Butterfly & Nature Conservatory. Spend the afternoon relaxing at Fort Zachary Taylor State Park and wrap up the day at Mallory Square for the Sunset Celebration before enjoying dinner at Latitudes. On Day 2, dive deeper into Key West’s unique culture with visits to the Harry S. Truman Little White House and the Key West Shipwreck Treasure Museum. Stroll through Duval Street, where you can shop, dine and experience the vibrant energy of the island. Finish your weekend with an evening at Key West Theater or a spooky adventure on the Ghosts & Gravestones Tour. By blending relaxation and exploration, you’ll make the most of your two days in Key West.