Key West was a stop on our cruise ship itinerary while working for the cruise lines.  With a day off, we would stroll through Duval Street ending with our last few moments watching the sunset over Mallory Square. Unfortunately, the ship would leave before the nightlife began and I had always wondered if it was as fun as I had always imagined.

For a long weekend, I packed my bags with a couple of my favorite bar-hopping friends to check out the night scene, starting at the infamous Irish Kevin’s.   With the motto, “I came, I drank, I don’t remember”, the southernmost Irish bar is a favorite among visitors to the Conch Republic.

Music was a big part of Kevin’s life as his father was an American Folk musician.  His only dream was to entertain and today he is living his dream.  Offering live music all day, there is a schedule of entertainers that perform, each with their unique talent.  The place is packed by nightfall and well into the time the place closes each night.  With fun singalongs and funny jokes, Irish Kevin’s keep Key West tourists entertained.

A visit to Key West wouldn’t be complete without a stop at Sloppy Joe’s and it is one of my favorite places, made famous by Ernest Hemingway.  My go-to drink is the Sloppy Rita made of Tequila, Triple Sec, Orange Juice, Sour Mix, Soda and as squeeze of lime.

Sitting at the bar, I struck up a conversation with the bar tender and learned that the current location is not the original Sloppy Joe’s, so I headed over to Captain Tony’s for a drink and a little history lesson.

Captain Tony’s Saloon is one of the most historic bars in Key West as the first and original Sloppy Joe’s bar in the early 1930s.  I pulled up Sean Connery’s chair at the bar and took a seat.  Inside are license plates hanging from the ceiling and dollar bills pinned up throughout the walls.  Interesting characters and celebrities have passed through these doors, not to mention the fascinating owner of this long-standing dive bar, Tony Tarracino.

First constructed in 1852, this location was once an ice house, a morgue, a cigar factory, a bordello and speakeasy before becoming the original Sloppy Joe’s, first opened by Josie Russell.  In 1968, Captain Tony purchased the bar and by the early 1970’s, Jimmy Buffett would make his debut, writing and singing his popular island tunes.

The Hog’s Breath Saloon was a short walk to try their Key Lime Shooter.  The bar was easy to find as we followed t-shirts with the famous slogan, “Hog’s Breath is Better than No Breath at All”. While the Original Hog’s Breath was first opened in Ft. Walton Beach, Florida, owner Jerry Dorminy was looking for a sunnier location and headed to Key West as far south as one could go.

If I wasn’t paying attention, I would have easily passed by “The Smallest Bar in the US.” Measuring the size of a small jail cell, it is one of the busiest bars in Key West.  We each ordered another Key Lime shot and decided to start our walk back to the hotel for the night.   Walking southeast along Duval Street, I recognized the Bull and Whistle and since it was on our way, we wanted a view of Duval from the second story balcony.

The lower level bar is The Bull, the second floor is The Whistle, while the top floor is the Garden of Eden, an adults-only bar.  From the second story, I could see that the night was slowing down and I wanted to take a photo of the Bull on Caroline Street (see the original bull from my second blog post, Key West, Florida – Looking Back on My First Visit in 1989, dated, January 19, 2014).

We had finally reached the Huron House and realized that we were more tired than we had thought.  With a couple of days of vacation ahead, we agreed to more rest so that we could explore the next day.

Have you visited the bars on Key West on Duval Street?  Do you have a favorite?  I would love to hear about your visit to Key West if you would kindly leave a message in the comments section below.

Many thanks for reading about my full day in Key West and wishing you many Happy Travels!

What to See and What to Do:

Irish Kevin’s 
211 Duval Street
Key West, FL 22040
Telephone:  305 292 1262

Sloppy Joe’s
201 Duval Street
Key West, FL  22040
Telephone:  305 294 5717

Captain Tony’s Saloon
428 Greene Street
Key West, FL  33040
Telephone:  305 294 1838

Hog’s Breath Saloon
400 Front Street
Key West, FL  33040
Telephone:  305 296 4222

The Smallest Bar Inn
124 Duval Street
Key West, FL  33040
Telephone: 305 240 0860

The Bull and Whistle
224 Duval Street
Key West, FL  33040
Telephone:  305 296 4545

Where to Stay:

Heron House
512 Simonton Street
Key West, FL  33040
Telephone:  305 294 9227

Where to Eat:

Sunset Tiki Bar – Located on the Marina
The Galleon Resort
617 Front Street
Key West, FL  33040
Phone: 305 295 0207

What to Eat:

• Ceviche
• Conch Fritters
• Crab Cakes
• Grouper
• Lobster
• Mahi Mahi
• Shrimp

What to Read:

• To Have and Have Not, by Ernest Hemingway
• Key West, Tequila, a Pinch of Salt and a Quirky Slice of America, by Jon Breakfield
• Gumbo Limbo, by Tom Corcoran
• Florida Keys Volume 1: A History of the Pioneers, by John Viele

Photo Guide to Key West:

• Casa Marina Key West
• Charming Houses and Front Porches
• Ernest Hemingway Museum
• Fort Zachary Taylor
• Hens and Roosters
• Higgs Beach
• The Kapok Tree
• Key West Lighthouse
• Key West Mural
• La Concha Hotel
• Marilyn Monroe at Tropic Cinema
• Mile Marker 0
• Mural at Waterfront Brewery
• The Old Pier Behind Casa Marina
• Rainbow Walkways at 801 Bourbon Bar
• San Carlos Institute
• Smathers Beach
• Southernmost Beach Cafe
• Southernmost House
• Southernmost Point Bouy
• The Strand