KEY WEST, FLORIDA | PERFECT DAY TRIP ITINERARY IN PARADISE

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Fun Ways to Get to Key West.

Before the adventure begins, getting there can be part of the fun:

Drive the Overseas Highway

A great way to immerse yourself in the Florida Keys adventure is to take Route 1. It winds over 42 bridges and 31 islands, giving you the most breathtaking views of the Atlantic Ocean and the Gulf of Mexico. 

Stop along the way at Bahia Honda State Park on Big Pine Key. It’s a great way to enjoy water activities, grab snorkel gear, and stop for a quick bite at one of the Keys’ local restaurants like Kiki’s Sandbar for the most AMAZING tuna nachos. ( We ate them twice!) Driving lets you control your schedule and explore at your own pace.

KEY WEST PRO TIP: The police are no joke about speeding & love to hang out at the bottom of ALL 42 bridges. Remember…you’re on Keys’ time now so slow down and enjoy all these stunning water views. We left with a souvenir!

Take the Key West Express Ferry

If you’d rather ditch the traffic or you don’t have a lot of time, then kick back and enjoy a relaxing ride on the Key West Express Ferry.  This super fun ferry runs from Fort Myers and Marco Island. You can book a round trip or a one-way ticket that drops you off in the heart of Key West. We booked our first trip to Key West this way and had a whirlwind 36-hour adventure!  So, sip a cocktail, watch dolphins play in the waves, and arrive in Key West ready to hit the ground running.

Fly into Key West International Airport

Flying is the fastest option, and next on our Key West bucket list! With flights from Miami, Fort Lauderdale, and other Florida hubs, this would be the ultimate excursion. No worries! The airport is smallish and just a short ride from Old Town. You can Uber, rent a bike, or a golf cart at the airport for a quick way to start exploring immediately.

KEY WEST PRO TIP: If you choose to rent a car, make it a small one. The streets are small and packed, and parking can be a nightmare for larger SUVs.

Ride a Scenic Bicycle or Motorcycle If You Dare

For the adventurous, bring a bike or rent one on the mainland and ride over the Lower Keys via the Overseas Highway. It’s challenging but unforgettable, with some of the best sunrise views you’ll ever see.

The Best Time to Visit Key West (Hint: It’s Always 5 O’Clock Here)…While Key West is absolutely beautiful year-round, (it is paradise after all), December through May is considered the best time to visit. September to mid-October is the off-season, while a great time to visit, note that many local businesses and restaurants shut down during this time.

Morning Magic: Breakfast, Butterflies & Botanical Bliss.

Breakfast at Pepe’s Café

Start your Key West day at Pepe’s Café, Florida’s oldest eatery since 1909. The menu features hearty omelets, homemade French toast, and one of their fresh-squeezed juices. We suggest grabbing a table outside, watching the roosters strut by, and soaking in the laid-back charm. While you’re at it, grab their signature Mojito and a TREAT!

Coffee at Cuban Coffee Queen

YES, PLEASE! After breakfast, get our FAVORITE Cuban-style caffeine boost at Cuban Coffee Queen. Their iced café con leche is strong and a little sweet, and perfect for powering through Key West Historic Seaport. Don’t forget to snap a photo by the “Welcome to Key West” mural. It’s an iconic memory marker for your perfect INSTAGRAMMABLE pic! Check out our blog post HERE!

Visit the Key West Butterfly & Nature Conservatory

Step into a tropical paradise filled with hundreds of butterflies, exotic birds, and lush tropical plants. Hands down, one of the best underrated Key West activities, and perfect for families. The gentle hum of butterfly wings and waterfalls makes it one of the island’s most serene spots. Grab a seat and enjoy the show. Scarlet and Rhett, the resident flamingos, are sure to put on! We concluded that we could have watched all day…

Explore the Key West Tropical Forest & Botanical Garden

This super amazing HIDDEN GEM (blink and you’ll miss it) offers a peaceful stroll with the iguanas and chickens through shaded boardwalks and Florida native plants right on the water. It’s the only frost-free subtropical conservation garden in the continental U.S., and a tranquil contrast to the lively streets downtown. Once one of three forts in the area, it was later used as target practice from Fort Zachary Taylor. 

Midday Adventures: Beach Time & Breezy Exploring.

Chill & Relax at Fort Zachary Taylor Historic State Park & Beach

Fort Zachary Taylor offers the perfect blend of history and beach time. WHO KNEW?! Swim, snorkel, or relax on powder white sands under Australian pines and swaying palm trees.

Ya’ll…we could spend the rest of our days being beach bums RIGHT HERE! With beach chair and umbrella rentals, snack bar, and water activity rentals, we just found Key West’s perfect hidden secret! SSHHH…don’t tell! We plan to ONLY hang here on our next visit!

The Civil War-era fort nearby is worth a quick exploration. Watch your step and enjoy the views from up top.

KEY WEST PRO TIP: Water shoes help with rocky sections, and the snack bar is great for sandwiches and smoothies. The chairs are also lush and padded. All we need now is a delicious umbrella drink!

Explore Key West By Bike or Golf Cart

Skip the traffic or endless walking and explore like a local by renting a bike or golf cart from FURY ADVENTURES. On our last adventure, we snagged a golf cart and had a blast exploring Key West.

Parking can be tricky in Old Town, so park once at a garage like the Old Town Garage or Park N Ride Garage and enjoy a leisurely ride around the island. We located a NOT SO CHEAP parking lot and later discovered more affordable options. They are there. Also note that parking a golf cart also has the same hourly requirements as a car.

Afternoon Highlights: Docks, Distilleries & a Curious Cemetery.

Take a Stroll in the Historic Seaport

The Key West Historic Seaport is pure island charm with fishing boats, sea breezes, and live music drifting from open-air bars. Grab lunch at Conch Republic Seafood Company or Half Shell Raw Bar, both famous for fresh catch and cocktails, and stunning views.

Key West Cemetery: Where the Living Visit the Witty Dead

Tucked away in the heart of Old Town, the Key West Cemetery is otherworldly. Established in 1847, it’s known for its quirky epitaphs and above-ground tombs that reflect the island’s humor and resilience.

Be on the lookout for gravestones with epitaphs like “I told you I was sick” or “At least I know where he’s sleeping tonight.” The cemetery sits on one of the highest points in Key West (a generous 18 feet above sea level, but who’s measuring), offering a surprisingly peaceful and uniquely Key West authentic can’t miss experience.

It’s a fascinating walk or ride (plenty of room for a golf cart) through local history, from soldiers and sailors to the island’s original Conch families. Bring water, a hat, and a sense of humor. Guaranteed to be a highlight of your Key West day trip adventure in paradise!

Tour the Key West Distilling Company

After you’re done hanging out in the cemetery, and only a few blocks away, visit Papa’s Pilar Distillery, on the corner of Greene & Simonton, for a fun, flavorful stop. Discover how Ernest Hemingway’s namesake rum and whiskey are made, and how it got its name.

This tour is NOT for the faint of heart- but a must-experience for sure. You’ll sample a few spirits(5 shots to be exact), so make sure you’re well-hydrated!  And when you’re done…

Have a Drink at Papa’s Pilar Social

Raise a glass at Hemingway’s Social Bar, and grab our fav, a Dark & Stormy! The live music, lively crowd, and cold drinks capture the spirit of old Key West.

If you have time, visit The Ernest Hemingway Home & Museum to see the writer’s studio, wander his beautiful gardens, and hang out with the famous six-toed cats lounging in the Florida sun.

Evening Indulgence: Key Lime Dreams & Sunset Magic.

AHHHH.…how we LOVE a fantastic sunset in the Florida Keys…here are our favorite go-tos for when the sun sets:

Grab the Perfect Slice of Key Lime Pie

Kermit’s Key West Key Lime Shoppe and Blue Heaven both serve tangy, creamy slices of the island’s signature dessert, and two of our favorites. Part of the total Key West immersion is to try EVERY key lime pie available!

Whether you choose to have it with whipped cream, frozen, dipped in chocolate, or meringue topping…either way, it’s a slice of paradise you won’t forget.

Head To Mallory Square For The Sunset Celebration

As day turns to dusk, make your way to Mallory Square. This nightly festival celebrates the sunset with live music, street performers, and unbeatable views of the Gulf.

Grab a drink, find a spot by the water, and watch the sky melt into gold and pink. It’s a Key West tradition and the perfect end to a perfect day.

Bonus Stops If You Have More Time.

• The Little White House– Explore the winter home of President Harry S. Truman. Fun tour and perfect for families.
• Duval Street- Bars such as Sloppy Joe’s and Green Parrot Bar, galleries, and quirky shops line the main strip.
• Key West Lighthouse & Keeper’s Quarters–  Climb 88 steps for breathtaking, panoramic views of the island.
• The Manatee Eating a Doughnut– Locate the iconic local painting famously known. HINT…it’s in the Bahama Village!
• Rooster Cemetery– Pay respects at The Blue Haven after indulging in the .best key lime pie.
• The House With A Billion Holiday Decorations– Ya’ll have got to see this! Truly amazing! Located at the 800 block of Whitehead Street in Key West, near the Hemingway House and across from the Key West Lighthouse.

PIN FOR LATER

What to Bring for the Perfect Key West Day.

• Reef Safe Sunscreen– Key West is literally on the face of hell year-round.
• Sunglasses and a wide-brimmed hat
• Cute Swimsuit, lightweight shirt with sleeves, and a towel
• Water shoes for hanging out at Fort Zachary’s beach
• Lightweight backpack – This backpack was the bomb! 
• Camera or phone with extra storage, waterproof case
• Refillable water bottle & Liquid IV(ESPECIALLY if you’re drinking)
• Cash for small vendors and parking (Meters also take a card)
• Comfortable walking shoes or flip-flops
• Light layer for breezy evenings
• A sense of humor and appetite for adventure

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Key West or Bust.

What has our hearts the most in Key West is the sun-soaked days, which are unhurried. The slower pace, lingering over a great lunch, and letting the island set our pace. So, whether you’re sipping a Keys libation by the ocean, biking under the peaceful swaying palms, or chasing that perfect sunset, one day in Key West is EXACTLY enough…and NEVER enough. HAPPY WANDERING!