Key West sits at the southernmost tip of the continental U.S., and what strikes you immediately is its unapologetically laid-back vibe. The island pulses with rich history, unforgettable sunsets, and a cast of free-roaming chickens and roosters strutting through the streets like they own the place. It’s a living collage of art, nature, and eccentric charm — impossible to ignore, and even harder to forget.
After spending a vibrant day in Miami, we set off toward Key West—a 164-mile journey that typically takes around four hours. The drive follows a mostly single-lane highway, with occasional passing lanes, making traffic during the summer months especially slow-moving. Despite recent improvements to the bridges and roadways, the growing number of travelers means driving still requires patience.
But this isn’t a route to rush. The highway meanders through charming little towns, each offering activities for both kids and adults—from quirky shops to waterfront parks. The bridges themselves are a highlight, stretching across vast expanses of turquoise water. Some are among the longest in the country, and their scenic beauty invites you to pull over and take in the marvel. New bridges now run alongside the older ones, blending engineering progress with historical charm.
The old bridges hold a special charm and purpose—they’re no longer just relics of the past but vibrant pathways for people to enjoy. Tourists often stroll or cycle along them, while locals use them for morning runs or peaceful walks. The most iconic of these is the Seven Mile Bridge, where we found ourselves lingering longer than expected, soaking in the views. During the summer months, bike rentals are available either in the nearby town or right at the parking lot, making it easy to explore at your own pace. The Seven Mile Bridge is one of the most iconic and scenic stretches of the Overseas Highway, connecting Marathon in the Middle Keys to Little Duck Key in the Lower Keys.
Modern Bridge (1982): The current Seven Mile Bridge is a precast segmented box girder structure built between 1978 and 1982. It spans 6.79 miles (10.93 km) and rises to a height of 65 feet, allowing boats to pass beneath. Old Bridge (1912): Running parallel is the original bridge, part of Henry Flagler’s Florida East Coast Railway extension to Key West. After the 1935 Labor Day Hurricane destroyed the railway, the bridge was converted for vehicle use in 1938. The Old Seven Mile Bridge is now closed to vehicles but open to walkers, runners, and cyclists, offering stunning views and a peaceful alternative to the highway. A 2.2-mile section leading to Pigeon Key was restored and reopened in January 2022, making it a popular spot for sightseeing and recreation.
Pigeon Key, a small island beneath the old bridge, once housed workers building the original railway. It’s now a historic site accessible via the pedestrian bridge. The bridge offers panora. Traffic can be slow, especially in summer, so it’s best to take your time and enjoy the journey. Bike rentals are available in nearby Marathon or at designated lots during peak seasons, making it easy to explore the old bridge on two wheels. Panoramic views of the Atlantic Ocean and Gulf of Mexico, especially breathtaking at sunrise and sunset.
It’s worth mentioning that many of these old bridges are now part of the legendary bike route that stretches from Key West all the way up to Maine. Cyclists like me often carry camping gear right on our bikes, embracing the full journey with a sense of adventure. It’s not just Americans who take on this path—riders from around the world come to experience it. I once met a British cyclist who was doing the same route. We crossed paths up north in St. Augustine, the oldest city in the country, sharing stories from the road.
We camped at Big Pine Key Campgrounds, a newer site that offered a truly memorable experience. Designed with care for both RVs and tent campers, the grounds felt welcoming and well-planned. Just beyond the campsite lies a dedicated deer habitat, adding a gentle touch of wilderness to the surroundings. A hiking trail loops through the habitat, perfect for a short stroll or nature walk.
After settling in, we enjoyed a simple snack with tea, then ventured out for a quick hike before sunset. We’d forgotten to pack a flashlight, so when darkness fell, we relied on the soft glow of our cellphones to light the way inside our tent. It was a quiet, cozy end to a peaceful evening under the stars.
It was a full moon night, and the sky was clear enough to capture some beautiful photos—the moon hung bright and bold above us. After soaking in the view, we tucked into our tent for the night. Not long after, the weather took a turn. Rain poured down and the wind howled through the campground.
Earlier that day, while setting up, I’d recorded a quick video on how to properly secure a tent—anchoring it firmly to withstand strong gusts. That preparation paid off. Despite the storm, our tent held steady. The noise of the wind and rain did wake us briefly, but with everything intact, we drifted right back to sleep, comforted by the shelter we’d built.
The next morning, after a hearty breakfast, we made our way to Key West—just a short drive from our campsite. One thing to keep in mind: parking isn’t free. Nearly everywhere you go, you’ll need to pay for parking, so it’s best to plan ahead.
You might assume that, being an island, beach access would be abundant and easy. Surprisingly, that’s not always the case. Many stretches of shoreline are private or not easily accessible, so finding a good public beach can take a bit of research. Key West offers several public beaches with easy access, including Fort Zachary Taylor Historic State Park Beach, Smathers Beach, and Higgs Beach—each known for its scenic beauty and visitor-friendly amenities. These spots feature sandy shores, picnic areas, and convenient parking, making them ideal for a relaxing day by the water.
The ocean here is crystal clear, and as you swim, you’ll often find yourself surrounded by vibrant, colorful fish. Occasionally, larger fish glide by as if they’re used to sharing the space with humans. Snorkeling is especially popular at these beaches, and gear is available for rent right on-site. Just like in Miami, the water gets deep quickly near the shore, so it’s wise to stay aware while enjoying the swim. Naturally, I captured some underwater footage with my GoPro—it was too beautiful not to.
One of Key West’s most iconic attractions is the Southernmost Point—a colorful, dome-shaped marker that boldly declares “90 Miles to Cuba.” It’s a popular photo spot, often surrounded by visitors capturing the moment. On clear nights, you might even spot a faint light on the horizon, said to be from Cuba itself.
The area around the marker is lively, filled with restaurants, bars, souvenir shops, and everyday stores. Adding to the charm are the free-roaming chickens and roosters that strut through the streets. Depending on the time of day, you’ll hear roosters crowing, giving the whole place a laid-back, farm-like vibe right in the heart of town. I couldn’t resist snapping photos of them all.
You’ll also spot iguanas basking in the sun—native to the region and just as much a part of the local character. It’s a quirky, colorful corner of Key West that blends tropical beauty with small-town charm. As you wander deeper into Key West, you’ll come across charming old houses that feel like a step back in time—preserving the character of the good old days. The streets are lively and compact, perfect for exploring by scooter, golf cart, or one of the tiny rental cars available. It reminded me of the winding alleys of Rome, Italy, where small vehicles rule the road.
Bike parking spots are painted in vibrant Pride colors, a nod to Key West’s long-standing connection to LGBTQ+ culture. The island has been a welcoming and celebratory space for decades. In fact, CNN often sets up a crew here on New Year’s Eve, broadcasting live from some of the popular bars alongside the Times Square ball drop. It’s a tradition that reflects the island’s festive spirit and inclusive vibe.
Fishing off the old bridges and piers in Key West is a beloved local tradition. I was captivated watching both kids and adults reel in fish with ease—it felt like a community ritual. Many of them cast nets to catch small baitfish, which they then used to lure in the bigger ones. I struck up conversations with several anglers, each with their own rhythm and story.
One of them, Gerard, told me he fishes on every day off, starting at 5 a.m. like clockwork. He proudly showed me his catch, and his enthusiasm was contagious. I also met a couple with an old Igloo cooler—complete with a built-in measuring scale to check fish size. Turns out, Igloo still makes those classic models.
I’ll admit, I’m not much of a fisherman myself and haven’t caught anything worth bragging about. But after meeting these passionate folks, I felt genuinely inspired to give it another shot.
🏛️ Historic & Cultural Highlights
• Ernest Hemingway Home & Museum: Tour the famous writer’s residence and meet the descendants of his six-toed cats.
• Harry S. Truman Little White House: A presidential retreat turned museum, offering a glimpse into post-WWII history.
• Key West Lighthouse: Climb for panoramic views and explore the keeper’s quarters.
🌅 Iconic Experiences
• Mallory Square Sunset Celebration: A nightly ritual with street performers, food carts, and ocean views.
• Duval Street: The heart of Key West’s nightlife and shopping, lined with bars, art galleries, and Cuban coffee spots.
• Key Lime Pie Tasting: Try the famous dessert at places like Kermit’s Key Lime Shoppe.
🌊 Outdoor Adventures
• Snorkeling & Diving: Explore coral reefs and marine life at Fort Zachary Taylor or via eco-tours.
• Kayaking in Mangroves: Paddle through serene waterways and spot wildlife.
• Fishing Charters & Sailing: Book a half-day trip or sunset sail with live music and drinks.
🐦 Nature & Wildlife
• Key West Butterfly & Nature Conservatory: Walk among hundreds of butterflies and exotic birds.
• Iguana Spotting: These native reptiles roam freely—great for candid photos.
• Wild Chickens & Roosters: A beloved part of the island’s character, often seen strutting through streets.
🎭 Quirky & Local
• Ghost Tours: Discover haunted sites and spooky legends on a nighttime trolley ride.
• Southernmost Point Marker: Snap a photo at the iconic buoy that reads “90 Miles to Cuba.”
• Bike Rentals & Scooters: Explore the island like a local—colorful Pride-themed bike racks add a festive touch.
🛍️ Shopping & Souvenirs
• Local Art Galleries: Find handmade crafts, tropical paintings, and nautical décor.
• Flea Markets & Boutiques: Great for picking up quirky gifts and beachwear.
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