So Much To Do In Key West

Sloppy Joes Bar Key West

When someone mentions Key West, you think sunshine, music and beachy cocktails. Having come from there just now, yes, yes and yes but so much more too! We found there was a lot to do in Key West, and here are our recommendations.

About Key West

Key West is known as Margaritaville after Jimmy Buffet, who lived and worked on boats there in his 20s. Much of the music style heard in the bars on Duval Street today is a descendent of Buffett’s “yacht rock”.

Key West street scene
Busy Key West streets

We learned a lot of bits of history on our tour with Key Lime Bike Tours, an entertaining 3 hour roll through the town’s highlights. Bike tours are generally a good way to get an overview and see a lot of a new place and this one was no different!

Key West is also known as The Conch Republic and got that name after a P.R. succession from the union to protest a government roadblock at the entrances to The Keys. It worked! Locals call themselves conches ever since.

We loved The Conch Republic and its residents. They embrace weirdness and like to have fun. Like Nashville and New Orleans, the bars are open early and full of live music. The restaurants are also good, serving local seafood and Cuban cuisine.


There is also a lot of history, mostly maritime related. Key West is known for “wreckers,” those who made their living salvaging wrecks and saving the people on them. And yes, the saving part was not their priority but had to be done to get to the valuables. We went to a museum dedicated to one man’s treasures from one wreck. The giant emerald at The Mel Fisher Museum was impressive and so were the photos and explanations of how the divers do their work salvaging shipwrecks. Mel Fisher is a legend! He spent decades trying to find this one wreck, made billions off of what he found on it, and when the state of Florida tried to take it all away from him, he took them to the Supreme Court and WON. Hero.

Mel Fisher Key West museum
The Mel Fisher Museum is a must do in Key West

More Key West History

The city is important in non-maritime history too. We visited a sculpture park with statues of many famous former residents, including Harry S. Truman and Ernest Hemingway, who both have museums in the homes they owned in Key West.

Visit Duval Street

You can’t go wrong visiting Duval Street, the Bourbon Street of Key West. It’s busier when there are cruise ships in town and it’s amusing to watch clumps of grandparents searching out the best happy hour deals.

We visited several drinking and dining establishments, including bars named The Half Shell Bar, Sloppy Joe’s, Tony’s Saloon, The Conch Shack and Hog’s Breath. Dive bars are the norm and packed at 11am on Tuesday.

Sloppy Joe's has live music all day do in Key West
Live music at Sloppy Joe’s, packed all day long

Tony’s Saloon is notably decorated in dollar bills and bras, while Hog’s Breath used license plates as wall coverings. The Conch Shack had the best key lime pie I have ever had and I tried more key lime pie these last 2 weeks than I should have.

Mallory Square

Another popular spot is sunset in Mallory Square. It’s so busy there between 5-6:15PM that the buskers have a lottery for the best times and locations to perform for the tourists.

In our short sunset visit to Mallory Square, we saw a flame juggler, a trained dog, a singer and acrobat, just some of the creative performers in Key West. We didn’t see the sunset, because it was too cloudy but I definitely recommend it as a fun thing to do in Key West.

Mallory Square
Juggler at Mallory Square

The weather was pretty rough for us – no rain, but lots of wind – so we didn’t spend a lot of time on the water except for sleeping. Our last night was probably our worst for sleep: the waves were really rough and the wind was strong and we rolled a lot. I didn’t want to leave my new favorite place, the best of the keys, but we had to come back north to prepare for our next adventure: the crossing to The Bahamas. It likely won’t happen for another week based on the wind and weather forecasts, but I’ll be posting!

Did I miss any of your favorite things to do in Key West? Let me know in the comments.

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Author: Mel

Living aboard a sailboat, blogging about the places we visit and the adventures we have. Love hiking, cycling, scuba, animals and adventure.

10 thoughts on “So Much To Do In Key West”

  1. I’ve never been to Key West but this sounds great. The Conch Republic looks like my kind of place but the wreckers history is interesting too.

  2. I have actually never been to Key West but it sounds like there is so much to do and explore there. Lots of inspiration in this post, hopefully I will make it there at some point!

  3. We have loved every visit we made to Key West. The laid back vibe has always been a draw for us. But the water sports is always our favourite thing to do with water all around you. A great spot for a short or long stop.

  4. My wife is obsessed with going to Key West and I never understood it. What is there to do, wondered a flummoxed I, except visit the Hemingway house and take walks in the sunset? After reading this, Key West reminds me of Provincetown, MA, in Cape Cod. The vibe seems familiar, the LGBT-bent, the destiny of dive bars, the embrace of weirdness, the promenade along the main street. I’m sure there are tea dances as well? The Cuban food you mentioned would be a serious draw, along with the general seafood offerings.

    1. I don’t know about tea dances, Tom, but the vibe is definitely about embracing the weird! In such a good way, well put!

  5. I have been wanting to visit the Keys for years, but staying in Key West always seemed too expensive. I love the dive bars you mentioned, you never really know what you’re going to get in a Florida bar, haha! Love the Hemingway aspect of it too, he had such an interesting life.

  6. I’m really hoping to make it to Key West soon so I was really interested in your experience. I didn’t realize it had a legacy of “wreckers.” I always associate wreckers with the Cornwall region of England!

  7. I’ve been to Key West once since I started my blog and I only got to spend about 24 hours there, so I still learned a lot from your post! I had no idea that it was such a hotspot for music and bar-hopping, nor did I know that this is the original Margaritaville! I will have to go back and spend more than a day here to check out all of the cool venues on Duval Street!

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