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My Key West Travel Guide

Finally! I’m recapping our recent Key West trip and all of the fun things that we were able to do and see in our few short days. I received so many helpful recommendations from you guys via Instagram and Snapchat, so I’m even adding in the suggestions that you sent over in case they help someone else plan their vacation to the Keys!

One of the BIGGEST travel tips for Key West that I can offer you. PACK LIGHT. If your plane – or your connecting plane – is very small, you will not be able to check more than one bag, and your carry-on will need to be very small in order to make it on the plane. Big fail on our part which set us back an entire day, so I cannot stress that enough! 

SECOND BIGGEST TIP: Bring a lot of SPF and skip the makeup and even bothering with your hair. Key West in June is SO hot and humid. Even this Louisiana girl was stunned at how heavy the air was! BUT it was pretty liberating walking around knowing that no one cared a bit at all about how you looked because they were sweating just as much.

Okay on to the good stuff. 🙂

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The Gates Hotel Key West

Where to Stay

The Gates Hotel Key West was our home-away-from home during our stay in the Keys. What’s really cool about this particular hotel? Well lots of things, let me list them! This motel-style property is new to Key West, and the rooms boast white-washed wood walls mixed with contemporary art and sliding barn-style doors. It’s like a much cooler version of your average-road-trip hotel complete with all the technological amenities including bedside smart tablets and USB ports right in the headboard.

There’s a permanent FOOD TRUCK on the grounds, and we may or may not have eaten nachos from it two days in a row. There’s also a very large outdoor bar next to the pool that also sits next to an outdoor stage where musicians come and play in the evening. The pool area includes lounge chairs, cabanas and even a sandy area complete with a hammock held up by two palm trees. There are also bicycles for rent on the property, so you can throw your things in a basket and take off! And speaking of taking off, you’ll be happy to hear the airport is SUPER close to this hotel meaning you won’t have to worry when you book a 5 am flight… ahem us.

There is a trolley/shuttle that shows up at The Gates Key West every five minutes past the hour to transport you conveniently downtown. This is a major plus since downtown is about a $20 cab ride from the hotel.


Bicycle rentals available at the Gates Hotel Key West
Famous crossing arrows are scattered across Key West – this one is right next to the Cuban Coffee Queen.

How to Get Around

This was a little bit of a first world hurdle for us. How do you get around Key West? Be forewarned that there are no Uber drivers here. (We are so used to using Uber that the first night in town, we actually started walking away from our cab without paying!!) We mostly got around by cabs from our hotel, but a lot of people will be whizzing by you on bicycles! (If you’re interested in the cabs, look for the pink Maxi cabs that are everywhere.) There are also shuttle options to downtown Key West available depending on your hotel.


The Gates Hotel Key West hosts a permanent food truck – The Blind Pig – from breakfast until dinner.
Kermit’s Kitchen is a must for their frozen chocolate-covered Key Lime Pie!

Where to Eat

Um hello fresh seafood and the most delicious Key Lime pie! Key West does not come up short in the food department, so you’ll be happy to know there are quite a bit of food options. Keep in mind, most restaurants are open-air and you’ll be lucky to find one with A/C. We actually sat in one place at the bar and ate because it was the only part of the restaurant with air conditioning!

And because Key West is called the Conch Republic, you HAVE TO try conch (pronounced conk, like conk yourself on the head). And what pray tell is conch? It’s the mussel that lives inside of those giant shells you hold up to your ear to hear the ocean. Sounds terrifying, but tastes delicious. Jenn and I split an order of conch fritters – basically tasted like delicious hushpuppies – but Key West offers all sorts of conch related dishes. We just decided to try the one we considered most “safe” because we are weenies. 

Here are a list of food suggestions:

Half Shell Raw Bar 

a/c in the bar / had my first conch fritter!

Kermit’s Key Lime Pie Shoppe 

for chocolate-covered key lime pie on a stick

Sloppy Joe’s

world famous bar and restaurant


the cutest wrap-around porch for people watching

Blue Heaven 

highly recommended for brunch and key lime pie

Cuban Coffee Queen

a must-see even if just for the photo!


Jungle Greg and Coco the rescue parrot on Duval Street!
Head to The Smallest Bar in the world on Duval Street and get a pineapple drink!
Head to the souvenir shops next to Cuban Coffee Queen and see all of the statues made from sea sponges + these colorful bouys.

Where to Go

There are so many things to do and see that we didn’t get to accomplish some of these, but I’m saving them on my list of things to do the next go ’round. I’m still mad that I have no photo with the Southernmost Point buoy! Basically if you wander around Old Town Key West long enough, you’re going to knock out at least half of these!

Mallory Square

Ernest Hemingway House

The Southernmost Point of the US buoy

The Butterfly Conservatory

The Smallest Bar

Smathers Beach

Rainbow Crosswalks


The Cuban Coffee Queen offers – of course – coffee and other Cuban foods.

Other Suggestions from you guys!

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  • Reply Carey

    Thanks for the great tips! Your outfits are so cute and bright, perfect for a vacation to the Keys!

    xo, Carey

    July 7, 2016 at 1:44 am
  • Reply Cynthia

    Great guide! I will be visiting in December

    September 16, 2018 at 5:31 pm
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