It’s no secret that Key West is undoubtedly one of my favorite places in the world. With the sunny days, tropical landscapes, vast ocean views and boundless activities to immerse yourself in, it’s certainly not surprising either. After finding myself answering some of the same questions time and time again, I thought it high time to put this information out there. If you’re going to visit, it’s important for you to learn what to expect in Key West.

This article explains all the details about the ins and outs of Key West. From location and sightseeing to vacationing with or without kids, all the details outlined below will help your understanding of what a vacation in Key West will look like for you.

Transportation

Firstly, getting to Key West is a breeze. The Key West International Airport is a small airport and extremely easy to maneuver. Flights from all over the country land here throughout the day, making it easy to access. Some choose to fly into Miami and rent a car to drive down through the Keys. This is a great day trip, for sure, if you’ve never driven through the Keys but can also be time consuming. Depending on traffic, it could take as many as 4-5 hours to drive from Miami to Key West.

Getting around Key West is most easily done by renting bicycles or scooters. It’s tricky to find parking spots and any that you do find, come with fees, of course. If you rent a bicycle or a scooter, parking is too easy and even better, FREE. Eaton Bikes is my favorite rental spot. I call them on my way into town, tell them what time I need my bikes delivered and where and they show up at my hotel and unload them for me. When I’m ready to leave, I let them know and they come back to pick them up!

Taxis and Ubers are plentiful in Key West. The local taxis line up right outside the airport so you can walk outside, hop in, ask to be taken to your hotel and away you go.

For getting around town easily, ride the Duval Loop. This FREE service is easy to hop on and hop off, throughout Key West. For more information on stops and times, click here.

If you’re in the Fort Myers area, the Key West Express is a great way to boat to KW for a short trip.

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The Vibe

Key West is famous for the party scene. Duval Street (the most famed street on the island) is lined with dive bars, upscale bars, rum bars, country bars and the like. What to expect in Key West, as far as vibes are concerned, is pretty well whatever you make of it.

If you want to party like a Rockstar until the sun comes up, there’s a scene for that. Are you looking to take a romantic trip, coupled with amazing drinks and food? There’s a scene for that. A fun girls trip? Yep, there’s a scene for that. Kids, you betcha, a scene for that.

Part of the allure of taking a Key West vacation is that anything goes and you get to make the trip what you want it to be.

Another word I frequently use to describe this tiny island is, “Funky”. Key West is funky, baby, and I love, love, love it. If you need a vacation where you can let your hair down and just let it be, Key West is where you should go.

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One Human Family

Judgement does not happen here. All nationalities and walks of life live and vacation in Key West, which comes together like one big melting pot in America.

It’s not unheard of to see an elderly man, wearing nothing but thong bottoms with bunny ears, casually walking the streets. Famous authors and musicians have vacationed here and also call Key West home. Artisans and business men and women, together, help comprise the fine people of Key West.

The Conchs are an accepting and welcoming group of people and are happy to have you come visit!

The Food

And then, there’s the food. Oh the amazing, yummy food. Steaks, lobsters, fresh Key West crabs, you name it, Key West has it. The food you will find here in Key West will impress you over and over again.

In addition to amazing food, are amazing prices. Like pricey, amazing prices. Breakfasts, lunches and dinners alike will hit hard on your pocketbook but every meal you’ll eat will be one you will remember, I assure you.

Our normal is to have breakfast out several times during our stay, one lunch out (always at Amigos) and dinners out every evening. When I’m on island time, there is no meal preparations happening from me. So, we buy some goodies at Fausto’s and use those snacks to make it through until the next mealtime.

You won’t get a meal you’re not pleased with in Key West. There’s so many wonderful restaurants to try and the ambiance is always on point!

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The Beaches

I hear visitors complain that they’ve heard the beaches in Key West aren’t great, or are nonexistent, and I’m here to tell you that is simply not true.

I love the beaches in Key West. Sure, they’re all man made, but they’re beautiful, nonetheless. The Key West beaches are well taken care of by the city and are restored every so many years. Dotted throughout the island, you’ll find all types of beaches for your taste. For a detailed article with locations and information on all the Key West beaches, read here.

Key West, and the other Key islands, are protected by the world’s third largest barrier reef, which prevents the natural washing up of sand that creates beaches. Hence, the man made ones. You won’t know the difference, I assure you!

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Chickens

In case this is the first time you’ve researched what to expect in Key West, I’ll warn you now. There are chickens that run freely all over the island.

As in, the chickens run freely all over the island. You’ll find them crowing early of a morning, down on Mallory Square. You’ll find them tending to their young in the yard of the Monroe County Courthouse. Heck, you’ll even find them trying to catch some grub on the floor at your restaurant, attempting to catch your dropsies.

I can’t love the chickens more. It’s part of what makes Key West eclectic and weird and totally awesome. The chickens and roosters are beautiful and are Instagram worthy, if that’s your thing.

Years ago, the chickens were brought to the island for cockfighting. Once that was finally outlawed, they were left to roam the streets and now we have all the cockfighting ancestors to look out for.

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The Night Life

Yes, Key West is famous (infamous?) for great night life on the island. Duval St is paramount for the bar scene. Here, you’ll find numerous hot spots that’ll keep you dancing into the wee hours of the morning.

Sloppy Joe’s, Captain Tony’s, The Smallest Bar, Hank’s Hair of the Dog and Willie T’s are some of the great ones to get you started.

If you’re an all night, party owl, Key West is definitely your kind of place. No worries if you’re not, though, because Key West is also the kind of place where it’s easy to get an after dinner cocktail, do a bit of people watching and call it an early night.

If you’re bringing your kids to KW, I would steer clear of Duval St after 9pm. Loads of debauchery happens here when the sun goes down.

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Accommodations

There is currently, such a demand for trips to Key West, that all the resorts, the small motels, the boutique B&Bs and vacation rentals have to be at the top of their game. They’re all dying for your reservations and know that competition is fierce.

My husband and I, along with our friends, have yet to stay somewhere that I wasn’t impressed with. Read reviews, ask for help from fellow travelers in the Key West Facebook Group and read this article to help you get started in your search of the best place to stay.

For those who are more resort goers with the large rooms and private beaches, search out some of the resorts along the edges of the island. If you love architecture and hospitality, look no further than the boutique hotels and bed and breakfasts dotted throughout town. Of course if you’re on a budget, even some of the smaller motels can provide you with a clean place to stay that’s affordable!

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The Landscape

When I’m in town, I generally try to get up and go for an early walk or run around town before it starts getting lively. This is my favorite time of day in Key West. It’s quiet. There’s a peace that envelopes the town and the stillness that you feel is polar opposite of what the town felt like the night prior.

You’ll see the locals riding their bicycles to work. The fishermen are gearing up the boats for their excursions that day. The sun begins to rise near the Southernmost Point.

This is when I take the time to truly look at the island and all she has to offer. The flowers and the greenery and the pure tropical beauty is something that puts me in awe every time I’m there. When it’s the dead of winter in Missouri, Key West is still in full bloom, every where you turn. There’s no better feeling, in my opinion.

Here, you’ll find banyan trees along Whitehead Street, orchids growing along the palm trees and birds of paradise as big as a house. Take a bit to explore and soak up the feeling of being alive among all these other things that are alive and well on the island.

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Attractions

One of the great draws of a trip to Key West is how rich in history this small island is. There truly is something for everybody here and many attractions are very reasonably priced.

Are you a history buff? Take a tour through the Hemingway House, a ride on the Conch Train or take a tour through the Key West Lighthouse.

For all the families with kiddos, you can see the flamingos, Rhett and Scarlett, at the Key West Butterfly Conservatory, or check out the sea life at the Key West Aquarium.

If you’re looking to relax, get a couples massage at Ocean Wellness and Spa, hire a private captain to take you to the sandbar, and spend the evening at Mallory Square.

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Key West with Kids

It’s been my opinion that Key West isn’t the best place for kids. Any of the Upper Keys, Islamorada, Marathon, Key Largo, yes. Key West, no.

However, all that being said, I do see and hear of more and more traveling with kiddos to the Southernmost Key.

Part of my worry has always been the transportation factor. Personally, we always rent bicycles and scooters, neither of which are safe with our young ones. But if you’re planning to use the Duval Loop (Key West’s FREE bus transit throughout the city) or if you rent a car (although I wouldn’t recommend), traveling throughout Key West could be a breeze with kids.

And honestly, there’s some really great things that kids would just simply enjoy. The beaches, firstly. Then you have The Butterfly Conservatory and the Aquarium. You have free evening entertainment every night at Mallory Square.

I am sticking to my guns on this one though. Keep the kids off Duval after 9pm.

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Have you ever been to Key West and have something great to add to this article? Post your comment below! If you’ve never been to Key West before and have questions about anything regarding What to Expect in Key West, also leave your comment below. I’m always happy to help direct fellow KW loving travelers!

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Other Key West articles that may interest you:

Key West Travel Advice: Where to Stay

Key West Beaches

The Top 10 Reasons I Love Key West

How to Pack for Key West

Renting a Vacation Home in Key West