3 Days in Key West: The Perfect Key West Itinerary

Discover the vibrant island charm, rich history, and crystal-clear waters of America's southernmost paradise. Follow this 3-day Key West itinerary for best results!

West Parker
West Parker
July 18, 2024

As my wife Sarah and I stepped off the plane at Key West International Airport, the warm, salty air hit us like a welcome embrace. We'd spent weeks planning our three days in Key West, poring over travel guides and pestering friends for recommendations. But nothing could have prepared us for the laid-back charm and vibrant energy that greeted us on this tiny island paradise.

Our taxi driver, a local named Chuck with a weather-beaten face and a wide grin, regaled us with stories of famous writers who'd found inspiration in Key West's bohemian atmosphere. "Hemingway, Tennessee Williams, you name it," he chuckled. "Something about this place just gets the creative juices flowing." As we drove down palm-lined streets past colorful conch houses, I could already feel the stress of everyday life melting away. Our 3-day Key West adventure was about to begin, and I couldn't wait to dive in.

If you're planning to spend 3 days in Key West, you're in for a treat. This Key West 3-day itinerary will take you through the best this tropical paradise has to offer, from historical sites to stunning beaches, and of course, the legendary Key West sunset celebration. So grab your sunscreen and let's get started on your perfect Key West itinerary!

Pre-Trip Planning: Making the Most of Your 3 Days in Key West

Before we jump into what to do in Key West for 3 days, let's cover some essential pre-trip planning. Knowing when to visit, what to pack, and how to get around will ensure your Key West 3-day itinerary goes off without a hitch.

Best Times to Visit Key West

Key West boasts beautiful weather year-round, but the best time to visit depends on your preferences. Here's a quick breakdown:

  • March to May: This is the sweet spot. The winter crowds have thinned out, hotel rates become more reasonable, and the weather is perfect with temperatures in the 70s and 80s.
  • June to November: If you're looking for the best deals, consider visiting during these months. Keep in mind that it's hurricane season, so keep an eye on the weather forecast.
  • December to February: This is peak season with perfect weather, but expect higher prices and larger crowds.

We chose to visit in April, and it was perfect – warm enough for beach days but not too hot for exploring the town.

What to Pack for Your Key West Trip

Key West has a casual, beach-town vibe, so leave your fancy clothes at home. Here's what you should pack:

  • Lightweight, breathable clothing
  • Multiple swimsuits
  • Sunscreen (reef-safe if you plan on snorkeling)
  • Sunglasses and a hat
  • Comfortable walking shoes and sandals
  • Insect repellent
  • Light rain jacket or umbrella (just in case)
  • Waterproof phone case
  • Reusable water bottle

Pro tip: Don't forget to pack a light sweater or jacket for evenings. While days are warm, it can get a bit breezy at night, especially if you're out on the water.

Getting To and Around Key West

Getting to Key West is half the fun! Here are your options:

  • Flying: Key West International Airport offers direct flights from several major cities.
  • Driving: The scenic Overseas Highway connects Key West to mainland Florida. It's a beautiful drive, but be prepared for traffic during peak seasons.
  • Ferry: Take the Key West Express from Fort Myers or Marco Island for a relaxing journey across the Gulf of Mexico.

Once you're on the island, you have several options for getting around:

  • Walking: Key West is small and walkable, especially if you're staying in Old Town.
  • Biking: Rent a bike to cover more ground. It's a popular and fun way to explore the island.
  • Duval Loop: This free hop-on, hop-off bus service is perfect for getting around the main tourist areas.
  • Taxis and ride-sharing services: Available if you need to go further afield.

We mostly walked and used the Duval Loop during our stay, which allowed us to soak in the island atmosphere and stumble upon hidden gems.

Where to Stay in Key West

Choosing the right place to stay can make or break your Key West experience. Here's a rundown of the best neighborhoods and accommodation options for your 3 days in Key West:

Key West Neighborhoods

  1. Old Town: This is the heart of Key West, featuring colorful Conch-style houses, historic sites, and the bustling Duval Street. It's perfect if you want to be in the middle of the action.
  2. Bahama Village: A vibrant neighborhood showcasing Key West's Afro-Caribbean heritage. It's great for foodies and those looking for a more local experience.
  3. Truman Annex: An upscale, gated community with well-manicured streets and proximity to popular attractions. Ideal for a quieter, more luxurious stay.
  4. Casa Marina: Known for its beautiful beaches and historic Casa Marina Resort. Perfect for beach lovers.
  5. New Town: A more residential area with modern amenities and local businesses. It's a bit removed from the tourist hotspots but offers a more authentic local experience.

Accommodation Recommendations

Key West offers a range of accommodations to suit every budget. Here are some top picks:

Budget-Friendly Options:

  • Southwinds Motel: A budget-friendly option with a pool and complimentary breakfast. It's just a short walk from Duval Street and Higgs Beach.
  • NYAH (Not Your Average Hotel): This unique hotel offers flexible room configurations perfect for groups or solo travelers on a budget.

Mid-Range Options:

  • Almond Tree Inn: This charming boutique hotel offers excellent amenities and a central location near Duval Street.
  • The Grand Guesthouse: A cozy bed and breakfast with personalized service and a quiet location.

Luxury Options:

  • Ocean Key Resort & Spa: Located at the end of Duval Street, this resort offers stunning views of the Gulf of Mexico.
  • Sunset Key Cottages: For ultimate luxury, stay in a private cottage on Sunset Key, just a short boat ride from Key West.

We chose to stay at the Almond Tree Inn for its central location and great reviews. The lush tropical courtyard and friendly staff made it the perfect home base for our 3-day Key West adventure.

Key West Safety Guidelines

While Key West is generally a safe destination, it's always good to keep a few safety tips in mind:

  1. Sun Safety: The Florida sun can be intense. Always wear sunscreen, stay hydrated, and seek shade during the hottest parts of the day.
  2. Water Safety: If you're planning water activities, always follow safety guidelines and be aware of current conditions.
  3. Bike Safety: If you're cycling, follow traffic rules and use bike lanes where available.
  4. Nightlife Safety: While Duval Street is lively at night, stay aware of your surroundings and don't leave drinks unattended.
  5. Hurricane Awareness: If you're visiting during hurricane season (June to November), keep an eye on weather forecasts.

Emergency Information:

  • Police/Fire/Ambulance: 911
  • Key West Police Department: (305) 809-1000
  • Lower Keys Medical Center: (305) 294-5531

Now that we've covered the basics, let's dive into our 3-day Key West itinerary!

Day 1: Historic Old Town Exploration

Morning: Duval Street and Breakfast at Blue Heaven

Bustling Duval Street in Key West with pedestrians, colorful shops, and lively bars, showcasing the heart of the island
Duval Street is the beating heart of Key West. I love how it comes alive at night with music pouring out of every bar!

Start your 3 days in Key West with a stroll down Duval Street, the main artery of Key West's Old Town. This mile-long stretch is lined with shops, bars, and restaurants, perfectly capturing the island's eclectic charm.

As you walk, you'll pass by colorful conch houses and quirky boutiques. Don't be surprised if you spot a few roosters strutting about – they're as much a part of Key West as the palm trees and ocean breeze.

Quirky outdoor dining area at Blue Heaven restaurant in Key West with free-roaming roosters, showcasing local charm
Breakfast at Blue Heaven is a must! The roosters roaming around add such a unique touch to the experience.

For breakfast, head to Blue Heaven. This Key West institution is famous for its "breakfast in paradise" served in a whimsical outdoor setting.

Why Visit: Blue Heaven offers a quintessential Key West dining experience with great food and a laid-back atmosphere.

Insider Tip: Try the Lobster Benedict or the Key Lime Pie Pancakes. They're both local favorites!

Key Information:

  • Location: 729 Thomas St, Key West, FL 33040
  • Hours: 8:00 AM - 2:00 PM, 5:00 PM - 10:00 PM daily
  • Price Range: $15-$30 per person for breakfast

Midday: Ernest Hemingway Home and Museum

Interior of Ernest Hemingway's writing studio in Key West, featuring his typewriter and desk, preserving literary history
Standing in Hemingway's studio, I could almost feel the creative energy. Did you know he wrote "For Whom the Bell Tolls" here?

After breakfast, it's time to dive into some Key West history at the Ernest Hemingway Home and Museum. This Spanish Colonial-style house is where the famous author lived and wrote for over a decade.

As you tour the house, you'll see Hemingway's writing studio and learn about his life in Key West. Keep an eye out for the descendants of Hemingway's six-toed cats – they still roam the property!

Why Visit: It's a must-see for literature lovers and history buffs alike, offering a glimpse into the life of one of America's greatest writers.

Insider Tip: Look for the penny embedded in the pool deck – there's a great story behind it!

Key Information:

  • Location: 907 Whitehead St, Key West, FL 33040
  • Hours: 9:00 AM - 5:00 PM daily
  • Admission: $17 for adults, $7 for children (6-12)

Afternoon: Harry S. Truman Little White House

Exterior view of the historic Harry S. Truman Little White House in Key West, a significant presidential landmark
The Little White House offers a fascinating glimpse into presidential history. Truman spent 175 days of his presidency here!

Continue your historical tour with a visit to the Harry S. Truman Little White House. This unassuming building served as the winter White House for President Truman and has hosted several other presidents over the years.

The guided tour offers fascinating insights into Truman's presidency and Key West's role in American history. You'll see the rooms where important decisions were made and get a sense of what life was like for the president during his Key West retreats.

Why Visit: It's a unique piece of presidential history in an unexpected tropical setting.

Insider Tip: Ask your guide about the "Key West Summit" – a lesser-known but significant event in Cold War history that took place here.

Key Information:

  • Location: 111 Front St, Key West, FL 33040
  • Hours: 9:00 AM - 4:30 PM daily
  • Admission: $22.52 for adults, $10.75 for children (5-12)

Evening: Sunset Celebration at Mallory Square

Lively sunset celebration at Mallory Square in Key West with crowd and street performers, capturing iconic daily event
The sunset celebration at Mallory Square is pure Key West magic. The energy of the crowd and performers is infectious!

As the day winds down, make your way to Mallory Square for the famous Key West Sunset Celebration. This nightly festival is a Key West tradition that you absolutely can't miss during your 3 days in Key West.

Arrive about an hour before sunset to enjoy the full spectacle. Street performers, food vendors, and artists create a carnival-like atmosphere as everyone gathers to watch the sun sink into the Gulf of Mexico.

Why Visit: It's the quintessential Key West experience, combining natural beauty with quirky local culture.

Insider Tip: For the best view, find a spot along the seawall. And don't leave right after the sun sets – the afterglow can be just as spectacular!

Key Information:

  • Location: 400 Wall St, Key West, FL 33040
  • Hours: Begins about 2 hours before sunset daily
  • Admission: Free

Night: Dinner and Drinks on Duval Street

Cap off your first day with dinner and drinks back on Duval Street. For a taste of Key West's seafood, try Pepe's Cafe, the oldest eating house in the Keys. If you're in the mood for something more upscale, Nine One Five offers sophisticated cuisine in a charming Victorian house.

After dinner, experience Key West's famous nightlife. Pop into iconic bars like Sloppy Joe's (a Hemingway favorite) or Green Parrot Bar for live music and strong drinks.

Remember, Key West has an open container law, so you can take your drink to-go as you stroll Duval Street. Just make sure it's in a plastic cup!

Day 2: Water Adventures and Nature

Morning: Dry Tortugas National Park Day Trip

Impressive Fort Jefferson surrounded by crystal-clear waters in Dry Tortugas National Park, showcasing natural and historical beauty
The ferry ride to Dry Tortugas is worth it for this view alone. The snorkeling around the fort is out of this world!

Rise and shine early for an unforgettable day trip to Dry Tortugas National Park. This remote island park, home to the impressive Fort Jefferson, is one of the highlights of any Key West 3-day itinerary.

The Yankee Freedom III ferry departs at 8:00 AM for the 70-mile journey. During the 2.5-hour trip, you'll be treated to stunning views of the Gulf of Mexico and maybe even spot some dolphins!

Once at the park, you can tour Fort Jefferson, a massive 19th-century fort with a fascinating history. After the tour, grab your snorkel gear (provided on the ferry) and explore the crystal-clear waters around the fort. The snorkeling here is some of the best in the Florida Keys, with vibrant coral reefs and colorful tropical fish.

Why Visit: It's a unique combination of history and natural beauty that you won't find anywhere else.

Insider Tip: Bring plenty of water, snacks, and sunscreen. There are no stores on the island!

Key Information:

  • Location: Ferry departs from 100 Grinnell St, Key West, FL 33040
  • Hours: 8:00 AM - 5:15 PM (ferry schedule)
  • Admission: $190 for adults, $135 for children (4-16) including ferry and park entrance

Afternoon: Key West Butterfly and Nature Conservatory

Vibrant butterflies on flowers at Key West Butterfly and Nature Conservatory, highlighting the delicate beauty of the attraction
Walking through a cloud of butterflies at the Conservatory was like stepping into a fairy tale. Keep an eye out for the flamingos!

After returning from Dry Tortugas, take a break from the sun at the Key West Butterfly and Nature Conservatory. This tropical paradise is home to over 50 species of butterflies and 20 species of exotic birds.

As you walk through the climate-controlled habitat, you'll be surrounded by hundreds of free-flying butterflies. It's a magical experience that feels worlds away from the bustling streets of Key West.

Why Visit: It's a serene and beautiful attraction that offers a unique glimpse into the world of butterflies.

Insider Tip: Visit late in the afternoon when the butterflies are most active. And keep an eye out for the flamingos, Rhett and Scarlett!

Key Information:

  • Location: 1316 Duval St, Key West, FL 33040
  • Hours: 9:00 AM - 5:00 PM daily
  • Admission: $15 for adults, $11 for children (4-12)

Evening: Smathers Beach Relaxation

Serene scene at Smathers Beach in Key West with beachgoers, palm trees, and tranquil waters, showcasing island relaxation
Smathers Beach is the perfect spot to unwind after a day of sightseeing. The gentle waves and soft sand are so soothing.

After a busy day, unwind at Smathers Beach, Key West's largest public beach. This two-mile stretch of sand is the perfect place to relax and soak up the last rays of sunshine.

Rent a beach chair or bring a towel and find your spot on the soft sand. The calm waters are great for a refreshing dip, and you might even catch sight of kiteboarders showing off their skills.

Why Visit: It's a beautiful spot to relax and enjoy a classic beach sunset.

Insider Tip: Stop by a local store and pick up some snacks and drinks for a casual beach picnic.

Key Information:

  • Location: 2601 S Roosevelt Blvd, Key West, FL 33040
  • Hours: Open 24/7
  • Admission: Free

Night: Dinner at Latitudes on Sunset Key

Romantic outdoor dining setting at Latitudes restaurant on Sunset Key, featuring stunning ocean views and elegant ambiance
Dinner at Latitudes is an experience to remember. The short boat ride over adds to the feeling of escaping to a private island.

For a truly special dining experience, take a short boat ride to Latitudes on Sunset Key. This upscale restaurant offers breathtaking views and exquisite cuisine.

The complimentary ferry departs from the Margaritaville Key West Resort Marina every 30 minutes. As you dine on fresh seafood and innovative dishes, you'll be treated to stunning views of the sun setting over the Gulf of Mexico.

Why Visit: It's one of the most romantic and picturesque dining experiences in Key West.

Insider Tip: Make reservations well in advance, especially for the coveted outdoor tables.

Key Information:

  • Location: 245 Front St, Key West, FL 33040 (ferry departure point)
  • Hours: Dinner served 5:30 PM - 10:00 PM daily
  • Price Range: $40-$60 per entree

Day 3: Cultural Immersion and Relaxation

Morning: Key West Shipwreck Museum

Intriguing display of shipwreck artifacts at Key West Shipwreck Museum, showcasing the island's maritime history
The Shipwreck Museum is a treasure trove of history. It's amazing to think about the stories behind each artifact!

Start your final day in Key West with a visit to the Key West Shipwreck Museum. This fascinating museum tells the story of Key West's maritime history and its once-thriving wrecking industry.

Climb the 65-foot observation tower for panoramic views of the island, then explore exhibits featuring artifacts from actual shipwrecks. The museum's actors bring history to life with entertaining presentations about the wreckers of Key West.

Why Visit: It offers a unique perspective on Key West's history and its relationship with the sea.

Insider Tip: Don't miss the short film about the Isaac Allerton shipwreck – it sets the stage for the whole museum experience.

Key Information:

  • Location: 1 Whitehead St, Key West, FL 33040
  • Hours: 9:30 AM - 5:00 PM daily
  • Admission: $17.50 for adults, $9.50 for children (4-12)

Midday: Fort Zachary Taylor State Park

Scenic beach at Fort Zachary Taylor State Park with historic fort visible, highlighting blend of nature and history
Fort Zachary Taylor State Park has the best beach in Key West, hands down. The snorkeling right off the shore is fantastic!

Next, head to Fort Zachary Taylor State Park for a mix of history and natural beauty. This Civil War-era fort is surrounded by one of the best beaches in Key West.

Start with a tour of the fort, which played important roles in the Civil War and Spanish-American War. Then, spend some time relaxing on the beach or snorkeling in the clear waters offshore.

Why Visit: It combines historical interest with beach relaxation, offering something for everyone.

Insider Tip: Bring water shoes if you plan to swim – the beach can be a bit rocky.

Key Information:

  • Location: 601 Howard England Way, Key West, FL 33040
  • Hours: 8:00 AM until sunset daily
  • Admission: $6 per vehicle, $2.50 for pedestrians and bicyclists

Afternoon: Key West First Legal Rum Distillery Tour

Interior of Key West First Legal Rum Distillery featuring rum barrels and copper still, showcasing local craft spirits production
The free tour at the Rum Distillery is super informative. Don't leave without trying their Key Lime Rum - it's dangerously good!

Cool off from the midday sun with a tour of the Key West First Legal Rum Distillery. This small-batch distillery offers free tours and tastings, providing insight into Key West's rum-running history and modern craft spirits scene.

Learn about the distilling process, see the equipment up close, and of course, sample some of their unique rums. From traditional silver rum to intriguing flavors like Key lime rum, there's something for every palate.

Why Visit: It's a fun and flavorful way to experience a different side of Key West culture.

Insider Tip: Try the rum cake – it makes for a great souvenir or gift.

Key Information:

  • Location: 105 Simonton St, Key West, FL 33040
  • Hours: Tours at 1:00 PM, 2:00 PM, 3:00 PM, 4:00 PM daily
  • Admission: Free (21+ only)

Evening: Sunset Sail with Sebago Watersports

Tourists enjoying a sunset sail with Sebago Watersports in Key West, capturing the beauty of the ocean and sky
There's nothing quite like watching the sun sink into the Gulf of Mexico from the deck of a sailboat. Pure bliss!

For your final evening in Key West, take to the water with a sunset sail. Sebago Watersports offers a variety of options, from laid-back sailboat cruises to more festive party boats.

As you sail out into the Gulf of Mexico, you'll be treated to unobstructed views of the famous Key West sunset. Many tours include light snacks and drinks, adding to the celebratory atmosphere.

Why Visit: It's a magical way to cap off your 3 days in Key West, combining stunning views with the thrill of being out on the water.

Insider Tip: Bring a light jacket – it can get breezy out on the water after sunset.

Key Information:

  • Location: 205 Elizabeth St, Key West, FL 33040 (departure point)
  • Hours: Typically depart 1.5-2 hours before sunset
  • Price Range: $60-$100 per person, depending on the type of cruise

Night: Farewell Dinner at Louie's Backyard

Picturesque oceanfront dining deck at Louie's Backyard in Key West, showcasing the restaurant's stunning location and ambiance
The view from Louie's Backyard is unbeatable. Their conch fritters are the perfect way to end a Key West adventure!

End your Key West adventure with a memorable meal at Louie's Backyard. This upscale restaurant, set in a Victorian home overlooking the Atlantic Ocean, is known for its innovative "Floribbean" cuisine.

Enjoy dishes that blend local seafood with Caribbean and Southern influences while soaking in the ocean views from the multi-level deck. It's the perfect setting for reflecting on your Key West experiences.

Why Visit: It offers a refined dining experience with a menu that captures the flavors of the Keys.

Insider Tip: If you're not ready for the night to end, head to their Afterdeck Bar for a nightcap under the stars.

Key Information:

  • Location: 700 Waddell Ave, Key West, FL 33040
  • Hours: Dinner served 6:00 PM - 10:00 PM daily
  • Price Range: $30-$50 per entree

Alternative Activities and Customization

While this 3-day Key West itinerary hits many of the highlights, there's always more to explore. Here are some alternative options to customize your trip:

For History Buffs

  • Custom House Museum: Learn about Key West's history through art and artifacts.
  • Key West Cemetery: Take a self-guided tour of this unique above-ground cemetery.

For Nature Lovers

For Foodies

For Families

Extending Your Trip

If you have more than 3 days in Key West, consider:

  • A day trip to nearby islands like Stock Island or Bahia Honda State Park.
  • A fishing charter to try your hand at catching some of the Keys' famous game fish.
  • A more in-depth exploration of the culinary scene, including a visit to a key lime pie factory.

Local Tips and Tricks

  1. Key Lime Pie: You can't leave Key West without trying this local dessert. Kermit's Key West Key Lime Shoppe is a popular spot, but don't miss the chocolate-dipped key lime pie on a stick at Key West Key Lime Pie Co.
  2. Happy Hour: Many bars offer great happy hour deals. Check out The Porch for craft beers or Alonzo's Oyster Bar for half-price appetizers and drinks.
  3. Free Entertainment: Besides the Sunset Celebration, look out for free concerts at Sunset Pier and street performances along Duval Street.
  4. Local Markets: Visit the Key West Artisan Market (Sundays) or the Petronia Street Farmers Market (Thursdays) for local crafts and produce.
  5. Conch Republic Independence Celebration: If you're visiting in April, don't miss this quirky 10-day festival celebrating Key West's "secession" from the U.S. in 1982.

Money-Saving Tips

  1. Use the Duval Loop: This free bus service hits most major attractions in Old Town.
  2. Visit during shoulder season: Late spring and fall offer good weather with lower prices.
  3. Look for combo tickets: Many attractions offer discounted rates when you buy tickets to multiple sites.
  4. Eat like a local: Try small, off-the-beaten-path restaurants for more affordable meals.
  5. Bring a reusable water bottle: Florida tap water is safe to drink, and you'll save money on bottled water.


As our taxi pulled away from the hotel on our last morning in Key West, Sarah and I found ourselves already planning our return trip. Three days in Key West had flown by in a whirlwind of sun-soaked adventures, historical discoveries, and culinary delights.

We'd watched the sun set from Mallory Square and from out on the water. We'd walked in Hemingway's footsteps and snorkeled in crystal-clear waters. We'd feasted on fresh seafood and key lime pie that tasted like sunshine. But most of all, we'd fallen in love with the laid-back charm and vibrant spirit of this unique island paradise.

Whether you're a history buff, a nature lover, a foodie, or just someone in need of a tropical getaway, Key West has something for everyone. This 3-day Key West itinerary barely scratches the surface of what the Conch Republic has to offer. So come with an open mind, a sense of adventure, and maybe an extra day or two if you can swing it. The southernmost point of the continental U.S. is calling, and trust me, you won't want to miss it.

Remember, the beauty of Key West lies not just in its attractions, but in its ability to make you slow down, relax, and embrace the island way of life. So don't stress if you can't fit everything in – there's always margarita o'clock at the nearest beach bar.

Safe travels, and enjoy your Key West adventure!

West Parker
West Parker
Article updated:
July 18, 2024 8:12 AM

West Parker, a Cornell University School of Hotel Administration graduate, has spent two decades as the secret weapon of the jet-set elite, crafting bespoke adventures that redefine luxury travel. Now a resident writer for Town & Tourist, this 45-year-old "Architect of Extraordinary Journeys" combines razor-sharp insights with unparalleled industry connections to deliver experiences that even the most discerning globetrotters can't help but rave about. West's expertise spans from exclusive real estate to fine dining, making him the go-to strategist for those who demand nothing but the extraordinary in their travels.

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