Key West, the southernmost point of the continental United States, offers a plethora of vibrant experiences, from breathtaking sunsets and historical landmarks to thrilling water activities and lively street performances. If you find yourself on a cruise that makes a stop at this enchanting island, make the most of your limited time with a well-planned 1 Day Key West Itinerary. In just one day, you can explore the highlights of Key West, immersing yourself in its unique culture, and creating unforgettable memories. Get ready to embark on a whirlwind adventure, filled with tropical delights and a laid-back island charm.
1 Day Key West Itinerary
Morning in Key West
Start your day with a hearty breakfast
In the beautiful and vibrant city of Key West, there’s no better way to start your day than with a hearty breakfast. Whether you prefer a traditional American breakfast or want to try some local specialties, you’ll find plenty of options to satisfy your appetite. Head to one of the charming cafes or restaurants in the Old Town area and indulge in delicious pancakes, eggs Benedict, or Cuban toast. A favorite among locals and visitors alike is Blue Heaven, known for its fluffy pancakes, tropical ambiance, and friendly atmosphere.
Visit the Ernest Hemingway Home and Museum
After fueling up with a delicious breakfast, take a step back in time and visit the famous Ernest Hemingway Home and Museum. This historic landmark was once the residence of the renowned American writer, Ernest Hemingway. Explore the beautiful Spanish colonial-style house and lush gardens, where Hemingway wrote some of his most famous works. Marvel at the vintage furniture and personal belongings of the author, and don’t forget to say hello to the resident six-toed cats, descendants of Hemingway’s original pets.
Explore Mallory Square
Next, make your way to Mallory Square, a bustling waterfront square that is famous for its lively atmosphere and breathtaking sunsets. During the day, you can browse through the vibrant local shops and boutiques, offering a wide range of unique souvenirs and local artwork. Grab a refreshing drink or snack from one of the many street vendors and take a moment to enjoy the stunning views of the Gulf of Mexico. Mallory Square is also home to the nightly Sunset Celebration, where street performers, musicians, and artisans come together to create a truly unforgettable experience.
Take a stroll along Duval Street
No visit to Key West is complete without a leisurely stroll along Duval Street. This iconic street is the heart and soul of the city, lined with charming shops, restaurants, and lively bars. From art galleries to clothing boutiques and souvenir stores, Duval Street offers something for everyone. Take your time to explore the unique shops and maybe even find the perfect gift or keepsake to remember your trip by. As you walk, you’ll also come across historic buildings and vibrant street art, adding to the charm and character of this vibrant street.
Mid-Morning Activities
Visit the Key West Aquarium
For those who love marine life and want to learn more about the local underwater ecosystem, a visit to the Key West Aquarium is a must. This family-friendly attraction offers a chance to get up close and personal with a variety of marine creatures, including sharks, turtles, and tropical fish. Take a guided tour, watch interactive feedings, and even have the opportunity to touch and hold some of the fascinating sea creatures. The Key West Aquarium is not only educational but also provides a unique and immersive experience for visitors of all ages.
Discover the Key West Shipwreck Museum
Step back in time and delve into the rich maritime history of Key West at the fascinating Key West Shipwreck Museum. This immersive museum offers a glimpse into the era of shipwrecks and salvage in the Florida Keys. Learn about the treacherous waters surrounding Key West and the brave men and women who risked their lives to salvage goods from wrecked ships. Through interactive exhibits and captivating storytelling, you’ll gain a deeper understanding of the island’s history and the impact of shipwrecks on its development.
Take a guided tour of the Truman Little White House
If you’re interested in politics and history, make sure to visit the Truman Little White House. This historic landmark served as a winter White House for President Harry S. Truman during his presidency. Take a guided tour and explore the rooms where Truman made important decisions and hosted dignitaries. Learn about the fascinating history of this presidential retreat and gain insight into Truman’s life and legacy. The Truman Little White House is not only a significant piece of American history but also offers stunning views of the surrounding gardens and waterfront.
Explore the Key West Butterfly and Nature Conservatory
Immerse yourself in the beauty of nature at the Key West Butterfly and Nature Conservatory. This enchanting tropical paradise is home to a vast array of colorful butterflies and exotic plants. Walk through the glass-enclosed conservatory and marvel at the fluttering butterflies as they dance around you. Learn about the different species of butterflies and their life cycles, and discover the importance of conservation efforts. The conservatory also features a tranquil garden where you can relax and enjoy the serene atmosphere.
Lunchtime in Key West
Enjoy fresh seafood at a local restaurant
Key West is renowned for its fresh seafood, so why not indulge in a delicious seafood feast for lunch? Head to one of the many local restaurants that specialize in serving the best catch of the day. From succulent shrimp and mouthwatering lobster to perfectly grilled fish, you’ll find an abundance of options to satisfy your seafood cravings. Some popular seafood establishments include Half Shell Raw Bar, Conch Republic Seafood Company, and Louie’s Backyard. Pair your meal with a refreshing tropical drink and soak in the laid-back atmosphere of Key West.
Try Key Lime Pie
No visit to Key West is complete without trying the iconic Key Lime Pie. This tangy and refreshing dessert is a local specialty that is loved by both residents and visitors alike. Made with fresh Key lime juice, a crunchy graham cracker crust, and topped with whipped cream, Key Lime Pie is the perfect sweet treat on a hot day. You’ll find this delectable dessert on the menus of most restaurants and cafes around town. Be sure to savor every bite and experience the true taste of Key West.
Grab a quick bite at a food truck
For those who prefer a quick and casual lunch, Key West is home to numerous food trucks offering a variety of culinary delights. From tacos and burgers to Cuban sandwiches and fresh ceviche, these mobile eateries serve up delicious bites that are perfect for a quick and satisfying lunch. Grab your food to-go and find a scenic spot to enjoy your meal, whether it’s by the beach or at one of the many picturesque parks in Key West. Don’t forget to try some of the local hot sauces and salsas to add an extra kick to your meal.
Dine at a waterfront restaurant
If you’re in the mood for a leisurely lunch with stunning waterfront views, Key West boasts an array of charming waterfront restaurants. Enjoy a relaxing meal while overlooking the crystal-clear turquoise waters and watching boats and sailboats pass by. Indulge in fresh seafood dishes, savory steaks, or mouthwatering tropical-inspired cuisine. With the warm sea breeze and panoramic views, dining at a waterfront restaurant in Key West is an experience to remember.
Afternoon Adventures
Go snorkeling or take a glass-bottom boat tour
Key West is famous for its vibrant coral reefs, making it a paradise for snorkeling enthusiasts. Dive into the crystal-clear waters and explore the diverse marine life that inhabits the reefs. Admire the colorful fish, sea turtles, and even the occasional stingray or nurse shark. If snorkeling isn’t your thing, you can still marvel at the underwater wonders by taking a glass-bottom boat tour. Hop aboard and cruise above the reefs, peering through the glass bottom to witness the breathtaking coral formations and marine life below.
Visit the Southernmost Point of the Continental U.S.
No visit to Key West is complete without a visit to the Southernmost Point of the Continental U.S. Located at the corner of South Street and Whitehead Street, this iconic landmark is marked by a colorful buoy that designates the southernmost point of the contiguous United States. Join the line of visitors waiting to take a photo with this famous buoy, and be sure to capture the moment to commemorate your visit to Key West. While you’re there, take a moment to appreciate the picturesque views of the ocean and enjoy the gentle ocean breeze.
Discover the Key West Lighthouse and Keeper’s Quarters Museum
For a glimpse into Key West’s maritime past, head to the Key West Lighthouse and Keeper’s Quarters Museum. Climb the 88 steps to the top of the lighthouse for panoramic views of the island and its surrounding waters. Learn about the history of the lighthouse and the role it played in guiding ships to safety during the 19th and early 20th centuries. Explore the restored keeper’s quarters, which provide a fascinating look into the daily life of the lighthouse keepers and their families. This historic site offers a unique opportunity to step back in time and experience a piece of Key West’s seafaring heritage.
Take a tour of the Key West Cemetery
For those with an interest in history and the macabre, a visit to the Key West Cemetery is a must. This charming and historic cemetery is the final resting place for many colorful characters, including pirates, smugglers, and notable Key West residents. Take a self-guided tour and wander through the labyrinth of gravestones, many of which tell intriguing stories about the lives of those buried there. Admire the unique and often humorous epitaphs and marvel at the eclectic mix of architectural styles. Despite its somewhat eerie reputation, the Key West Cemetery is a peaceful and fascinating place to explore.
Outdoor Activities
Relax at the beautiful beaches
Key West is blessed with stunning beaches, offering the perfect opportunity to relax and soak up the sun. Whether you prefer a lively beach with water sports and beach bars or a secluded spot away from the crowds, you’ll find a beach that suits your preferences. Smathers Beach, located on the Atlantic side of the island, is the largest and most popular beach. Here, you can rent beach chairs, umbrellas, and various water sports equipment. For a quieter and more secluded experience, visit Fort Zachary Taylor State Park, which boasts a beautiful sandy beach nestled amidst lush vegetation and historic fortifications.
Rent a bicycle or scooter to explore the island
With its compact size and flat terrain, Key West is the perfect place to explore on two wheels. Rent a bicycle or scooter and cruise around the island, taking in the sights and sounds at your own pace. Pedal or ride along the charming streets of Old Town, admiring the colorful Victorian houses and lush tropical gardens. As you explore, you’ll come across numerous historical landmarks and points of interest, such as the Southernmost House and the Key West Cemetery. Riding a bicycle or scooter allows you to cover more ground and discover hidden gems that may not be easily accessible by car.
Go kayaking or paddleboarding
For those who enjoy being on the water, kayaking or paddleboarding is an excellent way to explore the coastlines of Key West. Rent a kayak or paddleboard and set off on an adventure, gliding through the calm waters and observing the abundant marine life. Paddle along the mangrove forests, where you might spot herons, egrets, and even manatees. Enjoy the tranquility and serenity of the surroundings, as you navigate through the crystal-clear waters. Whether you’re a beginner or an experienced paddler, kayaking or paddleboarding in Key West provides a unique perspective of the island’s natural beauty.
Take a sunset cruise
There’s no better way to experience the beauty of a Key West sunset than by taking a sunset cruise. Climb aboard a sailboat or catamaran and set sail into the open waters, just in time to witness the sky come alive with vibrant colors as the sun sets on the horizon. Relax on the deck, sipping a cold drink as the boat gently glides through the waves. Watch as the sun dips below the water, casting a breathtaking glow across the sky. Many sunset cruises also include live music and even a champagne toast, creating a romantic and unforgettable experience.
Key West Art and Culture
Visit the Key West Art and Historical Society
For art enthusiasts, a visit to the Key West Art and Historical Society is a must. This cultural institution aims to preserve and showcase the rich artistic heritage of Key West. Explore the various galleries and exhibitions that feature a diverse range of artworks, including paintings, sculptures, and mixed-media installations. Learn about the significant role that Key West has played in inspiring artists throughout history, and discover the works of both local and internationally acclaimed artists. The Key West Art and Historical Society offers a fascinating insight into the artistic spirit of the island.
Explore the Studios of Key West
If you’re interested in discovering the vibrant local art scene, don’t miss the opportunity to explore the Studios of Key West. This nonprofit organization provides studio space for artists in various disciplines, including painting, sculpture, photography, and performance art. Wander through the studios and galleries, where you can witness artists at work and learn about their creative process. The Studios of Key West also host regular exhibitions, workshops, and performances, providing a platform for artists to share their work with the community. It’s a unique chance to immerse yourself in the creativity and talent that thrive in Key West.
Attend a live performance at the Key West Theater
Immerse yourself in the world of performing arts by attending a live performance at the Key West Theater. This historic theater, located in the heart of Old Town, showcases a diverse lineup of shows, including musicals, plays, concerts, and comedy performances. From local talent to nationally recognized acts, the Key West Theater offers an eclectic mix of performances that cater to all tastes. The intimate setting allows for a truly immersive experience, where you can connect with the performers and feel the energy of the live performances. Check the schedule and treat yourself to an evening of entertainment during your visit to Key West.
Discover the Key West Museum of Art & History at the Custom House
Step into the grandeur of the Custom House and discover the Key West Museum of Art & History. Housed in a magnificent historic building that once served as the island’s customs office, this museum offers a captivating journey through Key West’s past. Learn about the island’s maritime heritage, its connections to Cuba and the Bahamas, and the impact of the railroad on the island’s development. Explore the various exhibits that showcase the works of local artists, as well as artifacts that highlight the unique history and culture of Key West. The Key West Museum of Art & History provides a comprehensive and engaging experience for visitors of all ages.
Shopping in Key West
Browse unique boutiques on Duval Street
Duval Street is a shopper’s paradise, offering an array of unique boutiques and shops that cater to every taste. Browse through the eclectic mix of stores, where you’ll find everything from clothing and jewelry to handmade crafts and artwork. Discover locally made products and one-of-a-kind souvenirs that you won’t find anywhere else. Support local businesses and artists by purchasing their creations, and take home a piece of Key West’s vibrant culture and charm.
Visit the Key West Market
For a truly immersive shopping experience, visit the Key West Market. This vibrant and bustling open-air market is located at the corner of Caroline and Margaret streets. Wander through the stalls and embrace the lively atmosphere as you browse through a wide range of merchandise. From fresh produce and locally sourced products to handmade crafts and artwork, the Key West Market offers an abundance of unique and high-quality items. Take the opportunity to interact with the vendors, learn about their stories, and support the local economy.
Explore the Key West Bight
Located in the Historic Seaport District, the Key West Bight is a picturesque waterfront area that offers a mix of shopping, dining, and marina facilities. Stroll along the boardwalk and admire the colorful fishing boats and yachts that line the docks. Explore the charming boutiques and galleries, where you’ll find nautical-themed gifts, handmade jewelry, and maritime artwork. The Key West Bight is also home to several seafood markets, where you can purchase fresh catch to prepare at home. Don’t forget to pause and enjoy the view, as you watch the boats sail by and take in the vibrant ambiance of this waterfront gem.
Check out the Key West Historic Seaport
The Key West Historic Seaport is a vibrant and bustling district that reflects the island’s rich seafaring history. Here, you’ll find a variety of shops, restaurants, and attractions to explore. Browse through the maritime-themed stores, where you can find everything from nautical apparel and home decor to diving and fishing gear. Indulge in fresh seafood at one of the waterfront restaurants, while enjoying panoramic views of the marina. The Key West Historic Seaport also serves as a departure point for various water-based activities, such as fishing charters and sailing excursions. Immerse yourself in the maritime heritage of Key West and enjoy the lively atmosphere of this historic district.
Sunset and Evening Entertainment
Watch the famous Key West sunset at Mallory Square
As the day draws to a close, join the crowds at Mallory Square to witness the world-famous Key West sunset. This nightly Sunset Celebration has become a beloved tradition for locals and visitors alike. As the sun begins its descent, street performers and musicians gather to entertain the crowd with their talents. Breathe in the salty sea air, listen to the sounds of live music, and watch as the sky turns into a spectacular canvas of vibrant colors. This magical experience is best enjoyed with a refreshing drink in hand, as you bid farewell to the day and welcome the night in true Key West style.
Enjoy live music at one of the many bars and clubs
Key West is known for its vibrant live music scene, and there’s no shortage of bars and clubs where you can enjoy a night of great music. From lively dive bars to sophisticated jazz clubs, there’s something for every music lover. Grab a seat at one of the iconic venues along Duval Street and let the rhythms and melodies transport you to a different world. Whether you prefer rock, reggae, or acoustic tunes, you’ll find talented local musicians and touring acts putting on unforgettable performances.
Take a ghost tour or haunted pub crawl
For those seeking a dose of spooky entertainment, Key West offers a variety of ghost tours and haunted pub crawls. Embark on a guided tour through the dark and mysterious streets of Old Town, where you’ll hear chilling tales of the island’s haunted past. Visit places rumored to be haunted and learn about the eerie encounters experienced by locals and paranormal enthusiasts. If you’re feeling brave, combine your ghost tour with a haunted pub crawl, where you can enjoy a drink while listening to spine-tingling stories of Key West’s haunted past. It’s a thrilling and unique way to explore the darker side of the island’s history.
Attend a comedy show or improv performance
Laugh the night away at one of Key West’s comedy shows or improv performances. Several venues in the city host regular comedy nights, featuring both local comedians and touring acts. Sit back, relax, and let the comedians tickle your funny bone with their witty observations and hilarious anecdotes. If you prefer something more interactive, attend an improv performance, where the cast takes suggestions from the audience to create impromptu scenes and comedic sketches. Prepare for a night of laughter and entertainment that will leave you in high spirits.
Dining Options for Dinner
Experience fine dining at a high-end restaurant
If you’re looking for a memorable dining experience, Key West offers a variety of high-end restaurants that will tantalize your taste buds. Indulge in gourmet cuisine prepared by talented chefs, using the freshest local ingredients. From succulent seafood and prime steaks to innovative culinary creations, these restaurants are dedicated to providing a culinary journey like no other. With impeccable service, elegant ambiance, and stunning waterfront or garden views, dining at a high-end restaurant in Key West is an exquisite and unforgettable experience.
Try local specialties at a seafood shack
For a more casual and authentic dining experience, head to a local seafood shack and savor the flavors of Key West. These laid-back eateries specialize in serving up fresh seafood in a no-frills atmosphere. Feast on conch fritters, peel-and-eat shrimp, and blackened fish tacos, paired with a cold beer or a tropical cocktail. Enjoy your meal in a relaxed and friendly setting, where you can mingle with the locals and savor the true essence of Key West cuisine.
Enjoy a romantic dinner cruise
For a truly romantic evening, embark on a dinner cruise and enjoy a gourmet meal while sailing through the turquoise waters surrounding Key West. Glide across the waves as you savor a delectable meal prepared by skilled chefs, featuring a variety of culinary delights. Whether you prefer a sunset dinner cruise or a moonlit sail, this intimate experience offers breathtaking views, soothing sea breezes, and the perfect setting for a special occasion or a romantic date night. Sit back, relax, and let the beauty of Key West and the flavors of the gourmet cuisine captivate your senses.
Have a casual dinner at a beachside restaurant
Immerse yourself in the island vibe by having a casual dinner at a beachside restaurant. Enjoy a laid-back atmosphere with your toes in the sand as you dine on fresh seafood, tropical-inspired dishes, and refreshing cocktails. Listen to the sound of the waves and watch the palm trees sway as you relish the flavors of Key West. Whether you choose a seafood shack or a waterfront eatery, a casual dinner at a beachside restaurant captures the essence of the island and allows you to unwind and embrace the relaxed lifestyle of Key West.
Nightlife in Key West
Visit the famous Sloppy Joe’s Bar
No visit to Key West is complete without a visit to the legendary Sloppy Joe’s Bar. This iconic watering hole has been a beloved institution since its establishment in 1933. Step inside and be transported back in time to the days of Ernest Hemingway and the Prohibition era. Enjoy live music, sip on a classic cocktail, and dance the night away in the spirited atmosphere of this historic bar. With its lively vibe and friendly patrons, Sloppy Joe’s Bar is the place to be for a night of fun and revelry in Key West.
Dance the night away at a lively nightclub
For those who enjoy dancing and late-night partying, Key West offers a variety of lively nightclubs that cater to different tastes in music. From pulsating beats and electronic dance music to Latin rhythms and reggae vibes, you’ll find a club that suits your preferred style of dance. Put on your dancing shoes and join the energetic crowd, as you groove to the music and let loose on the dance floor. Key West’s vibrant nightlife scene ensures that the fun lasts until the early hours of the morning.
Enjoy a drink at a rooftop bar
For a more relaxed and upscale evening, enjoy a drink at one of Key West’s rooftop bars. Take in the panoramic views of the island, along with stunning sunsets and glittering city lights. Sip on craft cocktails, fine wines, or indulge in a glass of champagne as you watch the world go by from above. With their sophisticated ambiance and chic atmosphere, rooftop bars provide a tranquil setting to unwind and enjoy a memorable night out in Key West.
Try a craft cocktail at a speakeasy
Step back in time to the days of the Prohibition era and experience the thrill of a speakeasy in Key West. These hidden establishments offer a unique and intimate setting to savor the art of craft cocktails. Enter through secret entrances and whisper passwords to gain access to these clandestine bars. Inside, you’ll be greeted with a stylish and atmospheric setting, where skilled mixologists create innovative and handcrafted cocktails. Enjoy the delicious libations and embrace the speakeasy ambiance, as you immerse yourself in the allure of a bygone era.
Key West is a vibrant and diverse destination that offers a wealth of experiences for every traveler. From exploring historical landmarks and immersing yourself in the local art scene to indulging in fresh seafood and enjoying the lively nightlife, there’s something to suit every interest and preference. Whether you have a day or a week to spend in Key West, this comprehensive itinerary will ensure that you make the most of your time and create unforgettable memories in this tropical paradise. So pack your bags, put on your sunscreen, and get ready for an incredible adventure in Key West.
