Whether you’re a local looking for a quick getaway, an adventure lover or simply a traveler eager to discover every unique corner of this tropical paradise, Key West has an endless list of experiences. This itinerary is designed to give you the best day trip to Key West, filled with iconic sights, memorable activities and delicious bites that showcase the true spirit of the island.
Savor a Sunrise Breakfast at Two Friends Patio Restaurant
Kick off your one day in Key West with a visit to Two Friends Patio Restaurant, a beloved local establishment known for its laid-back ambiance and fantastic breakfast menu. Located in the heart of Key West, this charming spot is just a short stroll from many key attractions. Their Key West omelet, made with the freshest local ingredients, is a popular choice, bursting with flavors that reflect the island’s culinary style. Or, indulge in their French toast, topped with seasonal fruits that add a refreshing twist to this classic dish. The friendly service, lush setting and relaxed vibe make Two Friends Patio Restaurant a perfect starting point for your day trip to Key West, setting a warm and welcoming tone for the adventures ahead.
Explore the Historic Truman Little White House
After a delicious breakfast, head over to the Truman Little White House, a site rich in history and charm that offers a window into the past. Originally built as a naval command post in 1890, this house later served as the winter retreat for President Harry S. Truman, where he spent nearly 175 days during his presidency. As you step inside, you’re transported back to the mid-20th century, with each room telling stories of crucial decisions made within these walls. The guided tours offered here bring history to life, with knowledgeable staff sharing intriguing anecdotes about Truman’s time on the island and the events that shaped his presidency. From preserved artifacts to authentic furnishings, every detail in the Truman Little White House helps you connect to a significant era in American history. This visit is not only an enriching part of your one day in Key West but also an opportunity to walk through a piece of presidential history.
Hop on the Old Town Trolley Tour
To maximize your one day in Key West, hop aboard the iconic Old Town Trolley Tour, a trusted and convenient way to see the island’s most beloved landmarks. With the hop-on, hop-off flexibility, you can enjoy Key West at your own pace while listening to the entertaining and informative live narration from Old Town Trolley’s expert guides. They’ll share captivating stories, local lore, and insights into the island’s rich history and unique culture, bringing each stop to life.
The trolley takes you to key spots like Mallory Square, a bustling waterfront filled with local artisans and performers; the Key West Butterfly & Nature Conservatory, a serene escape with colorful butterflies in every corner; and the famed Southernmost Point, where you’re just 90 miles from Cuba. Each location gives you the chance to capture memorable photos, pick up distinctive souvenirs and immerse yourself in Key West’s vibrant atmosphere.
Wander Through the Ernest Hemingway Home & Museum
A day trip to Key West must include visiting the Ernest Hemingway Home & Museum, one of the island’s most famous landmarks. This historical residence, where the celebrated author wrote some of his most iconic works, is a treasure trove for literature lovers and history enthusiasts. As you wander through the rooms filled with Hemingway’s personal belongings, you’ll gain insight into his adventurous spirit and creative life. The museum’s unique residents — the famous six-toed cats that descend from Hemingway’s own pet — add a touch of charm and whimsy to the setting. Outside, the lush gardens offer a tranquil escape, with tropical foliage providing a beautiful backdrop to the Spanish Colonial architecture. Visiting the Ernest Hemingway Home is a highlight of any one day in Key West, offering an intimate look at the life of one of America’s literary legends.
Enjoy a Relaxed Lunch at Blue Heaven
Blue Heaven offers a truly unique Key West dining experience, bringing together the island’s laid-back charm with a menu full of Caribbean-inspired flavors. This well-loved spot, known for its lively surroundings and colorful decor — including whimsical artwork and free-roaming chickens — invites guests to enjoy an open-air meal under shady trees. With options like the famed fish tacos and the Blue Heaven burger crafted with fresh, local ingredients, every dish captures the rich flavors of the island. Pair your meal with an ice-cold tropical cocktail or a refreshing iced tea as you take in the distinct ambiance. Friendly staff, a relaxed vibe and the unmistakable character of Blue Heaven make this stop a memorable highlight of your day trip to Key West, offering a meal as memorable as the destination itself.
Snap a Photo at the Iconic Southernmost Point in Key West
The Southernmost Point Buoy stands as one of Key West’s most iconic landmarks, symbolizing its unique geographical position just 90 miles from Cuba. Painted in bold colors, this buoy has become a popular stop for both locals and visitors alike, offering a scenic backdrop of the Atlantic and a memorable photo opportunity. With the warm ocean breeze and panoramic water views, this spot embodies the relaxed, sun-soaked spirit of Key West. Take some time here to snap a keepsake photo, appreciate the surrounding scenery and soak in the buoy’s significance as the southernmost tip of the continental United States. Arriving early or in the evening often means shorter lines, allowing you to enjoy the relaxed ambiance of the area.
Discover the Haunted Side of Key West on the Ghosts & Gravestones® Tour
As twilight falls, add a bit of thrill to your one day 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 one day in Key West, leaving you with stories you’ll be talking about long after.
Dinner and Drinks on Duval Street
After your ghostly encounters, head over to Duval Street, Key West’s most lively strip and the heart of its nightlife. Known for its diverse lineup of bars, restaurants, and music venues, Duval Street is where Key West’s unique character truly comes to life after dark. Start with a stop at Sloppy Joe’s, an iconic spot with live music, great cocktails and a crowd that captures the island’s energetic spirit. For a more laid-back vibe, the Green Parrot Bar offers a local feel, with live music, strong drinks and a welcoming atmosphere. As you stroll along Duval, you’ll find an endless variety of entertainment options — from karaoke to live bands — that create the perfect end to a memorable day trip to Key West.
Conclusion
One day in Key West brings together adventure, history and a taste of the island’s unique charm. Starting with a sunrise breakfast, diving into historical landmarks, meeting ghostly legends and ending with an evening on Duval Street, this itinerary lets you experience the highlights of the island. Key West’s inviting atmosphere and mix of sights ensure a full day of memories, and no matter how you choose to spend it, the island will leave a lasting impression.
FAQs
What is the best way to explore Key West in a day?
For an unforgettable day trip to Key West, planning a structured itinerary with a blend of local dining, historical sites and must-see landmarks is key. Old Town Trolley Tours® is a fantastic option for those wanting to experience the island’s highlights with ease and convenience. This hop-on, hop-off tour lets you explore Key West’s attractions at your own pace while providing engaging and informative commentary from knowledgeable guides.
Are there family-friendly activities in Key West?
Absolutely! Key West offers a wide range of activities perfect for visitors of all ages, making it an ideal destination for families. The Key West Aquarium is a favorite for young visitors, offering interactive exhibits and close-up views of local marine life, from colorful tropical fish to fascinating sharks in the touch tank.
Where can I find the best sunset views in Key West?
One of the best ways to end your day trip to Key West is by witnessing the renowned sunset at Mallory Square. Known for its nightly Sunset Celebration, Mallory Square comes alive with a lively atmosphere as locals and tourists gather to watch the sun dip below the Gulf of Mexico. The scene is bustling, with street performers, musicians, and local vendors creating an unforgettable Key West experience. Grab a drink, browse local art stands and soak in the views of one of the most stunning sunsets you’ll find in the Keys — an ideal conclusion to a perfect day in paradise.
Is there a local art scene in Key West?
Yes, Key West boasts a dynamic and diverse art scene that adds depth to any visit. Scattered across the island, you’ll find galleries featuring works by local artists, outdoor murals, and creative public installations. Walking down streets like Duval and Whitehead, you can explore boutique galleries, street art, and artisan shops, each showcasing Key West’s creative spirit and unique artistic flair.
