I have written several full guides about Key West, from a budget guide for luxury backpackers, to a luxury guide for when money is no object. We currently live just outside Key West, and for the boy’s birthday this week we stayed overnight in order to hit up all of our favourite watering holes and eateries.
This is exactly how we spent out time, and my hidden gems for those who wish to spend 24 hours like a local!
Check in: 3pm
The Duval House is a great spot. Firstly, it is absolutely slap bang mid-way down Duval Street. For those who don’t know the town, Duval Street is the main street with all the shops, restaurants and bars on that runs from the infamous Mallory Square right down to the beach.
Secondly, it is very traditional and because of this is priced really well. It has a fabulous old charm and is completely spotless when it comes to cleanliness.
Thirdly, it is only for adults over 16, which means no children. Coupled with the quiet pool and tropical garden in it’s courtyard, it really is a quiet spot for a relaxing or romantic getaway.
We stayed in a deluxe room, and this was a beautiful airy room with antique furniture, a very comfortable bed, and breakfast included (not that we dragged ourselves up in time, you know how it goes).
My favourite little thing about this hotel? Not only that they provide organic toiletries, but they also supply make-up remover wipes! Now this certainly isn’t the best thing about the hotel by any means, but I just don’t see that very often and thought it was very cool… a nice touch for the ladies!
Pinchers is a crab and seafood place over looking Duval Street. Sit outside to experience the buzz of the street below, and enjoy two for one sangrias, margaritas, beers or wines during happy hour!
What we ate: snow crab, seafood pasta, sangria. It is seriously delicious!
From here we wandered down Duval, towards Mallory Square and hit up our first drinking hole:
Captain Tony’s Saloon is one of the most historical bars around. First of all it is a damn cool spot with live music most afternoons. Secondly, it has so much to see inside, including the great big tree which is right in the middle. This was a hanging tree back in the day, and the bar is said to be haunted by the bodies that were buried beneath. One of them is still inside; yep, there is a skeleton behind the bar! If the creepy stuff isn’t for you, just focus on the hundreds of bras that line the ceiling, the $1 bills stapled to the beams, or imagine Ernest Hemingway propping up the end of the bar.
What to drink: The rum punch is really good, and for $8 comes in a cup you can take away. It is a huge drink, so wander down the road with what you can’t finish (that’s the done thing in Key West) and sip on it during the sunset.
And…. be sure to try and throw a coin into the fish’s mouth above the sign outside.
The best place for sunset is Mallory Square, where the street performers and sellers gather to bring in the crowds as the sun sets. Despite the tourists, it is actually the most stunning sunset, and the street performers are pretty good (most of the time!).
Hog’s Breath Saloon:”Hog’s breath is better than no breath at all” is the catch phrase of this legendary bar. They have live entertainment all day, everyday, which makes it a damn cool place to catch some local music and soak up some Key West atmosphere. Plus it is right next to Mallory Square so you can head here just as you finish the last sip of your rum punch from Captain Tony’s!
From here we headed back to the hotel to drop off sun-hats, pop on some mascara (me, not him) etc. We then headed off Duval to escape the chaos for a while, and to go to another legendary Key West spot:
The Green Parrot: This is one of the coolest places to drink in the Keys. Not only is it really well established (in 1890!) it has some very funky art work, entertainment, and locals! Go here sober to take it all in (and leave drunk).
And… Be sure to check out the little library just outside the gift shop outside. It is the smallest library I’ve ever seen, and a typical example of the quirky Key West charm.
After a late lunch we found ourselves a little peckish after a few drinks, and headed next door to a newer addition to the Key West foodie scene. Charlie Mac’s has been around for about 4 years, and they have apparently taken that time perfecting the perfect brisket and BBQ sauce recipes. As well as being a pretty cool place to drink, with some really yummy cocktails, this place serves up some great food. The menu had me at ‘mac and cheese balls’ to be honest, but we ordered the nachos topped with brisket and Oh. My. Goodness they were amazing! (no photos due to the fact we couldn’t stop eating for long enough to turn camera on.)
Top tip for locals: Charlie Mac’s offers 50%(!) off food for locals!
Get The Party Started
There are ALOT of bars in Key West, but we never can do a night out here without hitting up Irish Kevin’s. Why? Well the boy has a tendency for ‘Irish Car Bombs’ (Baileys and Jameson shot dropped into half a Guinness… I know, I know). But it is a really buzzing bar with some hilarious live entertainment – kind of stand-up with a guitar. My dear friend Georgia ended up partaking in the Guinness downing competition when she was visiting from England. She didn’t win, but she did win my respect, for sure.
End the night
You are in Key West, you have to embrace the drag scene! The 801 Bourbon Bar really is a gay bar you can’t miss. In addition to their nightly drag shows, they have a really cool bar, and a few other rooms (never go in the back room, just don’t, trust me.) They have some cool artwork, and it is right next to Duval House, so bed is very near. (zzzzzzzzzzzzzzzzz).
Wakey, wakey, go shake that hangover with a dip in the pool. We
slept through ditched the hotel breakfast for a great Cuban spot, Havana, just a short walk down Duval from the hotel. They have A-MAZING biscuits and gravy, delicious bagels with cream cheese and smoked salmon, and really good coffee. It is highly recommended as a go-to breakfast spot.
The Best Coffee In Town
Okay so I rave about this place, but my absolute favourite coffee spot in Key West is Keys Coffee Co. They make delicious iced coffee’s, but my favourite is their nitro cold brew which I cannot visit Key West without grabbing a cup. It makes you feel like a million dollars and is really tasty. Plus because it is brewed for 48 hours it doesn’t give you any nasty side affects that strong coffee can. Just try it, trust me.
Wander Down Duval Street
Aside from the bars and restaurants, Duval has some fab shops and boutiques that are well worth popping into. There are plenty of great beach clothing and home wear stores amongst the touristy shops, and most people don’t leave town without buying something from the Hog’s Breath Saloon shop just by the bar itself. But don’t just stick to the main street. Hop off down any side street and you will find an array of cool cafes and shops. I love Key West Sunshine Club on Petronia Street for clothing (pictured below left), and Date and Thyme on Fleming Street for health food supplies and delicious smoothies.
Hit The Beach
We lounged by the pool at the Duval House (check out is 11am but they invite you to enjoy their pool and use their amenities for the rest of the day). If it is a beach that you are after for the rest of your stay then I recommend either Higgs Beach (free parking) or going to the state park Fort Zachary Taylor which has a lovely wild beach (they also have a small cafe and picnic tables) and is the ideal place to get away from the town and chill out for a while before heading on to your next destination.
So there it is, that is what I recommend for a smashing 24 hours in Key West. Feel free to check out any of my other Key West guides for alternative recommendations (links in beginning of post.)
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