Key West has a way of making time stretch. I came for a long weekend and left wishing I’d stayed for a month. With pastel cottages, teal-blue water, and roosters that strut like they own the place, this southernmost city in the U.S. feels more Caribbean than Floridian.
Whether you’re chasing history, sunsets, or just a few good mojitos, there’s something unforgettable around every corner. Here’s everything I loved (and a few surprises) from my trip to Key West—plus tips to help you plan your own.
1. Watch the Sunset at Mallory Square
This is one of those touristy things that’s actually worth doing. Each night, locals and visitors gather along the dock to clap as the sun dips into the Gulf. Street performers juggle fire, boats glide past, and the sky goes full watercolor.
Tip: Arrive 30–45 minutes before sunset to grab a good spot along the edge. Bring a drink, and stay for the energy—it’s infectious.
2. Explore the Ernest Hemingway Home
Even if you’re not a big literature buff, Hemingway’s Spanish colonial home is a peaceful oasis just off Duval Street. Wandering the rooms, I saw his old writing desk and met several of the six-toed cats that still live on the property.
Why I loved it: The gardens were unexpectedly calming, and learning about his wild Key West life made me want to reread The Old Man and the Sea.
3. Snorkel at Dry Tortugas National Park
This was hands-down my favorite day trip. I took the early ferry to Dry Tortugas, a remote national park about 70 miles from Key West. The water was so clear it looked Photoshopped. I snorkeled over coral reefs, explored Fort Jefferson, and sunbathed on powdery white sand.
Need to Know: Book your ferry at least a month in advance—it fills up fast.
4. Stroll Down Duval Street
Duval Street is Key West’s buzzing main artery. I walked the length of it twice—once by day to admire the historic homes, and once at night to bar-hop (my favorite stop was the divey yet iconic Green Parrot Bar).
Expect a blend of art galleries, Key lime pie shops, drag shows, and live music pouring out of open windows.
5. Visit the Southernmost Point Buoy
Yes, it’s a bit of a photo-op. But the Southernmost Point Buoy is an iconic marker, and it felt like a rite of passage to snap a selfie there. It’s only 90 miles from Cuba!
Tip: Go early in the morning if you want to skip the line.
6. Kayak Through Mangrove Tunnels
If you’re craving something quieter, I highly recommend a guided kayaking tour through the mangroves. I saw jellyfish, nurse sharks, and even a manatee while gently paddling through shady, narrow waterways.
What surprised me: How zen this felt after the buzz of Duval Street. It’s the side of Key West most visitors miss.
7. Indulge in Fresh Seafood (and Key Lime Everything)
I had some of the freshest seafood of my life in Key West. A few highlights:
- Garbo’s Grill (behind Hank’s Hair of the Dog) for Korean BBQ tacos
- Blue Heaven for brunch with live music and roaming chickens
- Conch Republic Seafood Company for oysters and waterfront vibes
And yes, I tried Key lime pie every day. My favorite was from Kermit’s Key West Key Lime Shoppe—tart, creamy, and dipped in chocolate.
8. Take a Sunset Sail
This felt like peak vacation. I boarded a catamaran with a local sailing company, sipped rum punch, and watched the sun sink into the sea with live music playing in the background. The breeze, the colors, the calm—it was magic.
Perfect for: Couples, solo travelers, or anyone who needs a moment to breathe.
9. Ride a Bike Around the Island
Key West is flat and bike-friendly. Renting a cruiser made it easy to explore quieter corners of the island, like the residential streets near White Street Pier or the peaceful Higgs Beach area.
Local tip: Use a map or GPS—some roads are one-way and can get confusing.
10. Visit Fort Zachary Taylor Historic State Park
A hidden gem for both history lovers and beachgoers. I walked through the Civil War-era fort, then laid out on the park’s beach (bring water shoes—it’s rocky) and snorkeled near the rocks. It’s a peaceful escape just a short bike ride from Old Town.
Things to Know Before You Go
- Best time to visit: December to April for dry weather and sunshine
- How long to stay: 3–5 days is perfect
- Getting around: Walk, bike, or hop on the Old Town Trolley
- Where to stay: I loved my boutique hotel near Simonton Street—quiet but walkable to everything
FAQs About Key West
What is Key West known for?
Sunsets, snorkeling, quirky culture, and being the southernmost point in the continental U.S.
Is Key West expensive?
It can be—especially during peak season. But happy hours, food trucks, and free activities like Mallory Square sunsets help balance things out.
Can you swim in the ocean in Key West?
Yes! Fort Zachary Taylor and Smathers Beach are popular spots. Just note that beaches here are smaller than in other parts of Florida.
Do I need a car in Key West?
No. It’s a walkable and bike-friendly island. If you’re staying in Old Town, everything is within reach.
What’s the weather like?
Expect tropical temps year-round. Summer is hot and humid; winter is warm and breezy.
Final Thoughts
Key West charmed me more than I expected. It’s quirky, sun-drenched, and filled with both energy and stillness. Whether you’re diving into shipwrecks, sipping rum on a boat, or just reading under a palm tree, it feels like a little world of its own.
If you’re planning a trip soon, check out my upcoming post on where to stay in Key West—including boutique hotels and luxury stays near the water.
Until then, happy travels 🌴
—Zee