Long Weekend in Key West: An Epic 3 Day Itinerary

Let’s get one thing straight—trying to slap an itinerary on Key West is like trying to put a leash on a cloud. This quirky little island, spanning just two-by-four miles, is all about kicking off your shoes and letting it all hang out. Here, you’ll master the art of “dolce far niente” (sweet doing nothing) better than any Italian ever could.

Forget rigid schedules and rules. Pick a few things you want to see and do, but follow them leisurely and with that unmistakable chill island vibe. Need some inspo? Check out our Key West bucket list in this blog for the must-do experiences.

Long Weekend in Key West: An Epic 3 Day Itinerary

Still need convincing? Think of Ernest Hemingway, who made this place home. His favorite pastimes—catching big fish, eating well, and drinking hard—still define the island’s charm. And let’s not forget the endless water sports and those jaw-dropping sunsets.

So where’s that quirky, laid-back vibe everyone falls in love with? It’s still here, tucked away in the nooks and crannies. You’ll find it biking through Old Town, savoring every bite of key lime pie, sipping a coffee or aperitif on a cozy front porch, and just soaking in the island’s chill vibes. Nail it, and Key West is still that magical place where time ceases to exist. There’s nothing to do and everything to do, all at once.

A Perfect Key West Itinerary

Fancy a weekend that’s as vibrant and spirited as you are? Key West, with its sun-soaked streets and eclectic charm, is calling your name. Let’s dive into a bold, unapologetically authentic itinerary designed to make the most of your weekend in paradise. 

Friday: Channel Your Inner Literary Genius

Morning: Pedal Through Literary History

Key West has been a magnet for literary giants, making it the perfect playground for book lovers and culture buffs alike. Grab a bike from WeCycle—they’ll even deliver it to your door at the Casa Marina resort. Start your self-guided tour at 1431 Duncan Street, the historic home of Tennessee Williams. Continue your ride to 624 White Street, where poet Elizabeth Bishop once lived, and then to 709 Baker’s Lane, the former haunt of “Midnight Cowboy” author James Leo Herlihy. Don’t forget to glide by Richard Wilbur’s writer’s compound at 713 Windsor Lane and Shel Silverstein’s pad at 620 William Street.

Cap off your tour with a visit to Casa Antigua at 314 Simonton Street, and the unmissable Hemingway Home on Whitehead Street, where the great Ernest Hemingway penned some of his most famous works. Just remember, no knocking—respect the current occupants.

Lunch: Dive into Local Flavors at Blue Heaven

Head to Bahama Village’s Blue Heaven for a taste bud explosion. This place isn’t just a restaurant; it’s an experience. Once a bordello and boxing venue (with Hemingway as referee), it’s now an eclectic eatery serving up mouth-watering dishes in an enchanting courtyard filled with roosters, a tiki bar, and live music. Pro tip: Don’t leave without trying the yellowtail snapper or the legendary Key lime pie.

Afternoon: Immerse Yourself in the Local Scene

Explore Coast Projects on Stock Island, where artists, musicians, and craftsmen collaborate to create a vibrant cultural hub. Check out their workshops, fundraisers, and film screenings. Then, head back to town and visit the Tropic Cinema. Restored by the Key West Film Society, this historic theater is a local favorite and a testament to the island’s dynamic arts scene.

Saturday: Sip, Cycle, and Soak Up the Sun

Morning: Coffee and Creativity at Coffee Plantation

A perfect day in Key West starts with coffee—preferably at Coffee Plantation. Settle into a comfy spot with a cup of their organic Blue Moon blend or a creamy café con leche. Owned by artists Diane and Theo Glorie, the café doubles as an art gallery, offering a feast for the eyes as well as the palate. Feeling inspired? Join one of their author readings or art shows.

Midday: Bike Around the Island

There’s no better way to see Key West than by bike. Feel the wind in your hair as you pedal along picturesque streets, discovering hidden gems and iconic landmarks. It’s eco-friendly, fun, and gives you the freedom to explore at your own pace.

Afternoon: Wander the Waterfront

Start at the Angling Company and take a leisurely stroll down Caroline Street to the Harbor Walk. This scenic route offers stunning views of the marina, coupled with the lively atmosphere of street performers and local vendors. Keep an eye out for unique boutiques and charming cafes along the way.

Sunday: Relax and Reflect

Morning: Brunch at a Local Favorite

Treat yourself to a leisurely brunch at one of Key West’s beloved eateries. Whether you opt for a classic eggs Benedict or a tropical fruit platter, you can’t go wrong. Take this time to savor the flavors, soak in the atmosphere, and reflect on your adventures.

Midday: Beach Bliss

Spend your final hours in Key West lounging on the beach. Find a quiet spot, lay down your towel, and let the sound of the waves wash over you. It’s the perfect way to unwind and bid farewell to this island paradise.

Afternoon: Departure with a Smile

As your weekend adventure comes to an end, pack up your memories and head home feeling rejuvenated and inspired. Key West has a way of leaving an indelible mark on your heart, and we have no doubt you’ll be back for more.

Make the Most of Your Key West Trip

Ready to experience Key West in all its glory? Embrace the spontaneity, the culture, and the sheer joy of discovery. Whether you’re a literary aficionado, a foodie, or just someone looking to escape the everyday grind, Key West offers something truly special. 

So, what are you waiting for? Pack your bags, hop on a bike, and prepare to fall in love with the island’s unmatched charm. Your perfect weekend itinerary awaits.

Remember, life’s too short for ordinary weekends. Make yours extraordinary in Key West. Safe travels and happy exploring!

Conclusion: A perfect Key West Travel itinerary?

Key West isn’t the kind of place where you follow an itinerary to a T. This little island paradise, measuring a mere two-by-four miles, is all about kicking off your shoes and feeling the freedom. But let’s get real: if you don’t do Key West right, you might end up more stressed than relaxed. Just take a stroll down lower Duval Street—it’s a chaotic mix of noise, sunburns, and daiquiris.