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Ultimate Weekend Itinerary for Key West

Key West offers a unique blend of history, charm, and outdoor adventure. Immerse yourself in the island’s past, explore coral reefs teeming with life, and savor delicious fresh seafood. Unwind on pristine beaches, soak up the festive Sunset Celebrations, and discover hidden gems along the way. Get ready for an unforgettable weekend getaway with this ultimate itinerary for Key West!

Itinerary for Key West


Morning (9 am – 12 pm):

Kick off the weekend in Key West with a narrated tour around the island to fully experience its charm. Old Town Trolley Tours and Conch Tour Train are popular options for unlimited hop-on, hop-off access during your stay. Both tours are fully narrated by knowledgeable and friendly guides who love to share Key West’s secrets, and stops are conveniently located throughout the island, allowing you to explore historic sites. Learn about the unique architecture, colorful characters, and history of the Conch Republic. Create your own customized itinerary for Key West and discover the magic of this island at your own pace.

While traveling through Bahama Village, Old Town, or Truval Village on your weekend in Key West, admire the charming pastel-colored conch houses and soak in the laid-back island vibes. Hop off at the Southernmost Point for a quirky photo opportunity. This iconic landmark marks the southernmost point in the continental United States. Or hop off at the Historic Seaport, packed with shops, restaurants, and historical sites offering a vibrant atmosphere and plenty to explore.

Afternoon (12 pm – 3 pm):

Hop off and grab a delicious lunch at El Meson de Pepe, a renowned Cuban restaurant serving authentic cuisine in a vibrant setting. This local favorite is known for its generous portions and lively atmosphere. Their menu features all the classics, such as ropa vieja (shredded flank steak) and flavorful Cuban sandwiches, served in ample portions. Don’t forget to try their famous mojitos or a refreshing mango daiquiri to complete the authentic Cuban experience. Fuel up for your afternoon adventures from this itinerary for Key West!

Immerse yourself in history during your weekend in Key West with a tour of the Harry S. Truman Little White House, a winter White House used by President Harry S. Truman. Originally constructed in 1890 as the headquarters of a naval station, it later became President Truman’s winter White House during his presidency. Over 11 visits, Truman spent a total of 175 days living and working in this charming house. Today, it stands as a historic site where visitors can tour the original furnishings, view Truman’s personal belongings, and step back in time to experience a glimpse into the life of the 33rd president.

Harry Truman Little White House

Craving some underwater adventure? Take a break from history and hop off at the Key West Aquarium! This exciting spot is perfect for curious minds of all ages. Come face-to-fin with exotic fish, sea turtles, and even sharks! The highlight for many kids (and perhaps even some adults!) is the touch tank experience. Here, you can gently get up close to some of the amazing sea creatures that call the Florida Keys home. This interactive experience is a must-add to any Key West itinerary!

Key West Aquarium

Evening (6 pm onward):

Conclude your first day in Key West with a spooky evening adventure on a Ghosts & Gravestones Tour. Delve into the haunted side of Key West as you listen to tales of restless spirits, shipwrecks, and local lore. These tours typically pass by the Key West Cemetery, renowned for its aboveground crypts and intriguing stories. As the sun dips below the horizon and Key West’s shadowy corners come alive, prepare for goosebumps and a newfound appreciation for the island’s fascinating, and sometimes frightening, history following this itinerary for Key West.


Morning (9 am – 12 pm):

Delve into Key West’s fascinating maritime history on the second day of your weekend in Key West with a visit to the Key West Shipwreck Treasure Museum. Explore captivating artifacts and exhibits that bring to life the perilous journeys of the island’s past. This museum houses treasures recovered from shipwrecks scattered across the Florida Keys, offering a glimpse into the dangers and rewards of maritime exploration. This is just a taste of what awaits you on this exciting itinerary for Key West!

Visit the Key West Butterfly and Nature Conservatory, a beautiful place to see butterflies from all over the world. Kids will love walking through the lush conservatory and watching the butterflies flutter around. Step into a lush climate-controlled habitat teeming with hundreds of free-flying butterflies from around the globe. The conservatory also houses fascinating bird species and a dedicated learning center, making it a perfect place for families and nature enthusiasts to explore the delicate beauty and importance of butterflies.

Key West Butterfly and Nature Conservatory

Afternoon (12 pm – 3 pm):

Head over to the Lobster Shack Key West, a beloved local eatery renowned for its mouthwatering lobster dishes, conveniently located near the Key West Butterfly and Nature Conservatory. This laid-back establishment prioritizes freshness and quality in its lobster offerings. Choose from a variety of lobster rolls, including classic New England style and unique Key West variations. Additionally, indulge in tempting options like lobster bisque and lobster BLTs. It’s the ideal spot to savor the flavors of the sea during your weekend getaway in Key West.

If you’re not in the mood for seafood, make sure to visit Sloppy Joe’s Bar, a must-see in Key West. Established in 1933, the year prohibition ended, it was a favored hangout of Ernest Hemingway and other literary giants. Today, Sloppy Joe’s pulsates with live music, dancing, and vibrant energy. Grab a drink, soak in the atmosphere, and imagine yourself rubbing elbows with the ghosts of literary heroes.

No visit to Key West is complete without exploring Duval Street, the vibrant heart of the island. This mile-long stretch is bursting with color and character, making it the energetic pulse of the island. Duval Street offers something for everyone — art aficionados can browse unique galleries, history enthusiasts can admire the well-preserved conch houses and food lovers can savor delicious cuisine from a variety of restaurants while shopping for souvenirs and local treasures. Don’t miss out on this essential part of your itinerary for Key West.

Duval Street

Evening (6 pm onward):

Head to Mallory Square for a vibrant Sunset Celebration — an essential experience on any Key West itinerary. Immerse yourself in the lively atmosphere filled with street performers, artisans, and vendors as the sun gracefully sets below the horizon. Enjoy the sounds of live music, savor a refreshing drink, and take in the breathtaking views. After the sunset spectacle, indulge in Key West’s renowned nightlife along Duval Street, where a plethora of bars, restaurants, and live music venues await, catering to every taste.

Mallory Square

Looking to elevate your sunset experience? Embark on a sunset cruise for an unforgettable conclusion to your weekend in Key West. Step aboard Fury’s Commotion on the Ocean Sunset Cruise for a dynamic evening on the water. This lively adventure combines the mesmerizing Key West sunset with live music and a festive atmosphere. Dance beneath the twilight sky on spacious decks as the sun dips below the horizon, all while indulging in delectable food and refreshing beverages. It’s the ideal way to cap off a day filled with excitement in Key West and create lasting memories.

Have an Extra Day?

A visit to Fort Zachary Taylor Historic State Park is a must on your itinerary for Key West, offering a fascinating look into the island’s military history. Or, discover the imposing 19th-century Fort Jefferson at Dry Tortugas National Park, reachable by hopping aboard the Yankee Freedom ferry for a full-day excursion during your weekend getaway. This park offers fantastic snorkeling and swimming opportunities, ideal for unwinding after touring the fort. Lounge on the beach, take a refreshing dip, and bask in the sunshine. Remember to pack sunscreen, sunglasses, and a hat — essential items for an enjoyable day exploring this historic site!


Are two days enough for Key West?

Yes, a two-day trip allows you to get a taste of everything that makes this island special! Hop on a fun Old Town Trolley Tour or the world-famous Conch Tour Train for a fully narrated historical tour of the island. Explore the fascinating Harry S. Truman Little White House or explore the island’s spooky side with a Ghosts & Gravestones Tour. Immerse yourself in the vibrant Mallory Square Sunset Celebration, or learn about Key West’s maritime past at the Key West Shipwreck Treasure Museum. Forty-eight hours in Key West pack a punch, leaving you wanting more!

What is Mallory Square known for?

Mallory Square, a vibrant hub in Key West, is renowned for its historical significance and lively atmosphere. It’s celebrated for its daily Sunset Celebration, where crowds assemble to witness the sun’s descent. The square, housing attractions like the Key West Aquarium and Key West Shipwreck Treasure Museum, also boasts an eclectic mix of shops and eateries. Its unique charm perfectly captures the spirit of Key West.

What’s the best time to go to Key West?

The best time to visit Key West is generally during spring, from March through May. The weather is pleasantly warm with less rainfall, and you can enjoy outdoor activities and attractions comfortably. The city is less crowded, as it’s not the peak tourist season, offering a more relaxed experience. Remember, however, that the exact timing can depend on what you want to do, so always check the local weather and event calendar when planning your trip.