Key West, Florida: A Relaxed and Remarkable Island Escape
Where the road begins… and ends.
Standing at the start (or finish!) of the iconic Highway 1 in Key West—a reminder that every journey has a story, and some of the best ones start here.
Tucked away at the very southern tip of the continental U.S., Key West, Florida, is the kind of place that sneaks into your heart and makes itself at home. With its rich history, mouthwatering local eats, and breezy island charm, it’s a destination that invites you to slow down, savor the moment, and soak up something special—whether you're traveling with family or just carving out a little solo adventure.
A Stroll Through Hemingway’s World
Step into the world of Ernest Hemingway
His beautifully preserved Key West home is a slice of literary history—lush gardens, six-toed cats, and all. A must-see for book lovers and curious travelers alike.
One of my absolute favorite stops in Key West was the Ernest Hemingway Home and Museum. Even if you’re not a huge literature buff, this place is pure magic. You wander through lush gardens and a gorgeous Spanish Colonial home where Hemingway actually lived and wrote—yes, the very same spot where he finished writing, A Farewell to Arms, in 1930.
Inside, the home is lovingly preserved, filled with antique furniture, original photos, and personal mementos that offer a window into Hemingway's colorful life. Don’t miss the writing studio where masterpieces were born, perched in a separate building behind the main house.
And let’s talk about the cats. Dozens of them roam the property, many with six toes, all descended from Hemingway’s own beloved kitties. There’s something kind of whimsical and grounding about it, like history and everyday life blending together. You almost expect Hemingway to pop out of the study, mid-thought, muttering about his next sentence.
Accessibility Note:
The first floor of the home, grounds, and museum store are mobility device accessible, however the top floor of the home, including Hemingway’s writing studio require climbing stairs. There is a video guide of the upstairs quarters on the first floor.
The Southernmost Point: A Picture-Perfect Pause
The Southernmost Point Buoy in Key West isn’t just a colorful photo op—it’s a true American landmark.
The buoy has become one of the most photographed spots in the Florida Keys. Expect a bit of a line, especially at sunrise and sunset, but the view—and the sense of being at the edge of the map—is worth it.
Just a short walk from Hemingway’s place is the iconic Southernmost Point Buoy—a vibrant, oversized marker that proudly claims its spot just 90 miles from Cuba.
It’s one of those must-do photo ops, but it’s also a moment of reflection. Standing there, breeze in your hair, with the ocean stretching out before you, you really feel it: you're at the edge of something. Simple. Beautiful. Meaningful. This concrete buoy has stood since 1983 and has weathered many storms—both literally and figuratively. Visit early in the morning if you want to avoid the lines, or go in the golden light of late afternoon for that perfect shot.
Accessibility Note:
The Southernmost Buoy is fully accessible to mobility devices.
Key West Aquarium
Sharks, turtles, and touch tanks—oh my!
The Key West Aquarium is where island history meets underwater discovery, and it's a splash for all ages.
The Key West Aquarium is a small-town shift from the large aquariums you may be used to. Located right in the heart of Old Town, in Mallory Square, the Key West Aquarium is a family-friendly spot packed with fascinating marine life. Opened in 1935, it's one of Florida’s oldest aquariums and still one of the most charming. You’ll find everything from sea turtles and stingrays to sharks and colorful reef fish.
Kids can enjoy hands-on experiences at the touch tanks in the outdoor area, and educational feedings happen throughout the day. It’s an ideal indoor activity for a warm afternoon or to wind down at the end of a busy day before heading back to your hotel.
Conch Fritters: Crispy, Golden Goodness
Crispy, golden, and straight from the sea—conch fritters are a Key West must-try!
These island bites are packed with flavor and local flair, best enjoyed with a splash of hot sauce and a side of sunshine. Don’t leave without tasting this true Florida Keys classic!
Let’s talk food—conch fritters, to be exact. These crispy, golden bites are a Key West staple, and once you try one, you’ll understand why.
I recommend grabbing some from The Conch Shack, where the vibe is relaxed, the drinks are cold, and the flavors are unforgettable. The fritters are made with tender conch meat, a seasoned batter, and just the right amount of crunch. Pair your fritters with a tangy dipping sauce, a cold mojito, and a shady seat under a palm tree, and you’ve got the ultimate island snack. It’s a bite of local flavor you’ll be craving long after you’re home.
Mallory Square: Where Sunset Becomes a Celebration
Sunsets aren't the only show at Mallory Square!
As the sky lights up, so does the street—with jugglers, magicians, musicians, and all kinds of island magic. It’s a nightly celebration where the performers are as colorful as the sky.
Mallory Square is a hub for visitors and locals alike where you will find restaurants, shops, museums, and the Waterfront Playhouse.
Every evening in Key West, something magical happens at Mallory Square. Locals and visitors gather for the nightly Sunset Celebration, and it's just what it sounds like: music, laughter, street performers, and an epic sky show as the sun sinks into the Gulf.
Jugglers toss flaming torches, musicians strum island tunes, and local artisans sell handmade goods while the sky turns shades of tangerine and lavender. It’s festive, a little chaotic, and full of charm. Whether you grab a spot by the water or wander through the crowd with a frozen drink in hand, it’s a joyful moment you’ll carry with you long after the sun has set.
Sip Like Hemingway: Sloppy Joe’s & The Green Parrot
The Green Parrot isn’t just a bar—it’s a Key West institution.
Unpretentious, full of character, and always buzzing with live music and local vibes, it’s the kind of place where stories start and time slows down. Come for a drink, stay for the soul of the island.
Still feeling that Hemingway vibe? Don’t miss a stop at Sloppy Joe’s, one of the author’s favorite watering holes. It's lively, a little rowdy, and full of character—just like you’d imagine. Grab a bar stool, order a sloppy joe or fish sandwich, and soak up the live music and local chatter.
If you’re looking for something more low-key, head over to The Green Parrot, another Hemingway haunt with a more laid-back, locals-only kind of charm. This dive bar has been around since the 1800s, serving cold drinks and good times to generations of visitors and Conchs (that’s what locals are called). It’s the kind of place where you order a drink, lean back, and just be.
Duval Street: The Heart of the Island
Duval Street is a treasure hunt with a tropical twist!
Shopping, snacking, and strolling down Duval Street—because in Key West, even window shopping feels like an adventure.
Ready to explore? Duval Street is the beating heart of Key West—colorful, quirky, and full of energy. From art galleries to cute boutiques, coffee shops to Cuban restaurants, this street has it all.
You can start your day with a strong Cuban coffee, pop into a few locally-owned shops, grab lunch at a breezy sidewalk café, and finish with a slice of Key lime pie. And in between? Street performers, live music, and maybe a rooster or two strutting across the sidewalk. It’s the kind of place where every turn holds a surprise and every stop has a story.
Fort Zachary Taylor Historic State Park
History meets paradise at Fort Zachary Taylor!
From exploring Civil War-era cannons to snorkeling just steps away from the fort walls, this spot blends the best of Key West’s past and present. Perfect for curious minds, beach lovers, and anyone who likes their history with a sea breeze.
For a dose of history and natural beauty, make time to visit Fort Zachary Taylor Historic State Park. Built in the mid-1800s, this coastal fortress played a vital role in both the Civil War and the Spanish-American War. You can explore the old red-brick fort with its massive cannons and underground tunnels, then take a short stroll to one of Key West’s best beaches.
The park is perfect for families and history buffs alike—bring a snorkel, pack a picnic, and enjoy a full day under the sun and surrounded by the stories of the past.
Pro-Tip:
The beach rocky and surrounded by coral reefs which is great for snorkeling, but not for bare feet. To ensure you have the great time you have been looking for, make sure to bring water shoes for everyone in your travel party.
The Key West Lighthouse and Keeper’s Quarters
Climb to the top of the Key West Lighthouse and you’ll earn more than just a view you’ll touch a piece of island history.
From the original Keeper’s Quarters to the sweeping 360-degree vistas, this stop is part adventure, part inspiration, and all Key West charm.
Another must-see historical gem is the Key West Lighthouse and Keeper’s Quarters Museum. Originally built in 1848, the lighthouse has helped guide mariners safely to shore for over a century. Climb the 88 steps to the top for panoramic views of the island and sea—you can even spot Hemingway’s house from the top.
The museum gives a fascinating look into the lives of the keepers who maintained the light, including one of the first female lighthouse keepers in the country. It’s a powerful reminder of the people who kept ships safe and Key West connected to the rest of the world.
Accessibility Note:
There is an 88 step climb to get to the top of the lighthouse
There are three steps to get into the Keeper’s Quarter’s Museum
There is a video of the lighthouse museum exhibits available for viewing in the keeper’s quarters.
The grounds and restrooms of the Lighthouse and Keeper’s Quarters are flat and mobility device accessible
Why Key West Belongs on Your Travel List
Key West isn’t just a destination—it’s a feeling. It’s the salty air, the sounds of live music floating down the street, the stories tucked behind every pastel-painted door.
Whether you're traveling with your grandkids, your partner, or simply treating yourself to some well-earned adventure, this island has a way of turning moments into memories. And if you're like me—someone who caught the travel bug later in life—Key West reminds you that it's never too late to explore somewhere new and let it surprise you.
Accessibility Note:
While the sidewalks and roads provide around Key West adequate surfaces for strollers and mobility devices, during peak times, the number of people exploring the island can create congestion on the sidewalks and paths which may make them difficult to navigate.
Bicycles are a popular transportation option for many visitors to Key West. You may find bikes locked to streetlights and signs leading to blocked sidewalks and walkways.
Planning a cruise, or a trip to Key West? I’d love to help you make it unforgettable. From multigenerational travel tips to personalized itineraries, I’ve got you covered. Contact me here for a free travel quote!
