6 Best Bars In Key West

Above, Sloppy Joe's Bar is number one on the list. Photo by Armand Vaquer.

Back in 2019, the Cuba cruise I was on stopped for a few hours in Key West, Florida. I had a great time there. I toured the Shipwreck Museum and the Hemingway House. I also mangaged to shop at a great cigar shop and have a couple of margaritas at an outdoor bar.

Above, yours truly enjoying a margarita at El Meson de Pepe.

The Infatuation has posted an article listing the six best bars in Key West.

They begin it with:

If finding a great bar in Key West seems daunting, it’s only because the island can feel like one never-ending bar. On seemingly every block, you’ll find chairs with waterfront views, stools within earshot of someone strumming an acoustic guitar, and places that claim to have hosted Ernest Hemingway. The good news is that there aren’t any bad choices when going out in Key West. Just keep your drink orders simple, because cutting-edge cocktails aren’t really a thing here. And know that Duval Street, often called Key West’s Bourbon Street, is where you’ll find the most (and rowdiest) bars. 

If the thought of taking shots with wandering bachelor parties makes you shudder, though, this guide has plenty of options off Duval, with all the Jimmy Buffett vibes that made you book a room here in the first place. And when you get hungry, check out our guide to the best restaurants in Key West.

 Sloppy Joe's Bar is number one on the list. Strangely, there's also a Sloppy Joe's Bar in Havana, Cuba.

To read more, go here.

Cigar City USA and El Meson de Pepe Bar

Above, Mark Cesani and his Cigar City USA Indian. Photo by Armand Vaquer.

While in Key West, Florida last week, I stopped at the Cigar City USA store to get a couple of cigars.

During my time at the store, I had a lengthy conversation with manager Mark Cesani about cigars and cigar store Indians. His Indian caught my attention as it was about five feet tall. He said he paid $3,000 for it. He isn't worried about anyone stealing it as it is quite heavy. It stands at the entrance to his store from the El Meson de Pepe restaurant and bar.

I showed him photos of my cigar store Indian and he said I got a good deal for mine.

He had a good selection of cigars and I found his prices to be reasonable.

Above, the El Meson de Pepe bar. Yes, one can smoke cigars at this bar! Photo by Armand Vaquer.

Following our visit, I headed to the El Meson de Pepe bar for some margaritas and to smoke one of the cigars I bought at Cigar City USA. Since the Key West area is considered to be Jimmy Buffett territory, I thought having a couple of margaritas would be appropriate. Buffett has recorded at a small studio near the marina.

Above, one of Key West's inhabitants wandering around the El Meson de Pepe restaurant. Photo by Armand Vaquer.

Throughout Key West, there are chickens running loose everywhere, and that included this restaurant. El Meson de Pepe serves Cuban cuisine.

After my cigar and margarita break, I did some more wandering around.