Today, we’re going to take you around and show you what to do in Key West Cruise Port, sharing everything we loved about our recent trip exploring this colourful and quirky corner of the Florida Keys. From the moment you step off the ship, you’re greeted by pastel-painted houses, swaying palms, and that unmistakable laid-back island vibe.
We’ll wander along lively Duval Street, packed with boutique shops, open-air bars, and historic architecture, before heading to the iconic Southernmost Point marker for the must-have photo. We’ll pop into Ernest Hemingway’s House to meet the famous six-toed cats, pause at Mallory Square to watch the street performers, and sample the creamiest Key lime pie you can imagine.
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Exploring Key West Cruise Port: What To Do When You Visit
Along the way, we’ll share tips for renting bikes or hopping on the Conch Train, point out the best spots for fresh seafood and frozen cocktails, and show you quiet side streets where roosters roam freely and hidden gardens offer a peaceful break from the buzz. Whether you have just a few hours in port or an entire day, our guide will help you soak up the charm, history, and sunny spirit that make Key West a true Caribbean-style escape right in the USA.
From historical landmarks and quirky shops to beach bars and chickens roaming the streets, Key West is unlike anywhere else we’ve visited. Best of all, it’s an easy walk right from the cruise ship, no excursion needed!
Can You Walk Into Key West From The Cruise Port
As you dock in Key West, where usually only one ship is allowed at a time, you’ll step off the ship and be right in the heart of town. It’s one of the easiest cruise ports to explore independently, with everything just a short walk away.
The first thing you’ll spot just outside the port to the left is Custom House, a beautiful historic building. From there, we headed left and stumbled across a lovely little arts and crafts market, which is well worth a browse. Turn right just beyond the market and you’ll find an ATM if you need one.
From the Custom House, if you continue walking left, you’ll find yourself heading towards Mallory Square, a vibrant area full of attractions. Along the way, you’ll see Conch Train Tours and trolley tours, both excellent guided options for exploring the island. They offer hop-on-hop-off services and are usually more affordable if you book through sites like GetYourGuide rather than the cruise line.
There’s even a free shuttle service called the Duval Loop (more on that shortly), perfect if you’d rather not walk the entire island.
Plan Your Trip
Check out these handy links to help you booking your next trip.
Family-Friendly Attractions Near Key West Port
Key West has plenty to keep the whole family entertained. Just a few steps away, you’ll find the Shipwreck Museum and the Key West Aquarium, both fantastic stops if you’ve got children with you. The aquarium even has sea turtles!
Right beside the Shipwreck Museum, there’s an artisan market selling handmade gifts, a great place for unique souvenirs.
My absolute favourite shop was the Shell Warehouse. It’s more than your typical gift shop, it’s packed with high-quality shells, gorgeous tea towels, and the most stunning Christmas decorations. I couldn’t resist picking up a few! If you’re into festive decor, this is the place to stock up.
1. Take A Stroll Through Key West’s History
Just around the corner from the Shell Warehouse, you’ll find the Key West Historic Memorial Sculpture Garden. It’s a lovely green space filled with statues and plaques honouring individuals who played a key role in shaping the island’s history. Take a few minutes to read the stories, they’re fascinating.
Also, keep an eye out for the chickens! They roam freely all over Key West and are considered part of the local charm.
For that iconic cruise ship selfie, head through Mallory Square to the waterfront. From there, you’ll get a fantastic backdrop of your ship and the sea, ideal for that holiday photo to remember your trip.
2. Catching the Free Duval Loop Bus
Once you’ve had your photo moment, head back past Custom House towards Green Street, where you can catch the Duval Loop, Key West’s free bus service. It loops around the island, stopping at major attractions including the Southernmost Point, Whitehead Street, the Hemingway House, and the Lighthouse Museum.
3. Visiting Hemingway’s House
One of our top highlights was visiting Ernest Hemingway’s House. We hopped off the Duval Loop bus on Whitehead Street and walked straight in, no long queue, no need to book in advance. The house offers a free guided tour or you can explore at your own pace.
It’s full of intriguing stories, from Hemingway’s adventures and writing habits to the famous six-toed cats that still roam the gardens today. There’s even a little replica house just for them!
4. Lighthouse Museum and Southernmost Point
Just a bit further down is the Key West Lighthouse Museum. If the weather isn’t too hot, you can climb to the top for panoramic views of the island. We decided to continue on to the Southernmost Point, but be warned, it gets very busy. We skipped the long queue and snapped our photo from the side, which still gave us a great view.
5. Stop The Southernmost Cafe
Right nearby, we stumbled upon a chilled beach bar known as the Southernmost Café. It’s got a relaxed, beachy vibe and serves great snacks, cold beef and wine. The sea here is a bit wild for swimming, but it’s a lovely spot to sit and enjoy the view.
6. Walking Back Down Duval Street
From there, we made our way back along Duval Street, a must-visit if you’re in Key West. The houses are pretty, the chickens are still everywhere, and the vibe is wonderfully diverse.
It’s the perfect street for people watching, with quirky shops, themed bars (one had walls and ceilings covered in signed dollar bills!), and vibrant decorations. We visited just after Valentine’s Day, and the town was still decked out in red hearts and festive cheer.
7. Check Out The Street Art
There are also rainbow walkways, peace signs, and so much character. It took us about an hour to walk the length of Duval Street, but that included lots of stops for drinks and photos. You could easily do it in 30 minutes if you’re short on time.
8. One Last Stop Before the Ship
Just before we returned to the port, we discovered a converted truck bar with a tented area at the back, complete with air con. A fun and unusual spot to grab a last drink before heading back to the ship.
And as we boarded, the cruise crew were waiting with cold drinks, a perfect end to a fabulous day.
Key West A Florida Dream
Key West was absolutely incredible and one of our favourite stops in the Caribbean on our Celebrity Apex Cruise. Its mix of history, charm, character, and ease of access makes it a top contender for any future cruise itineraries.
