Wine Dine and Play: Captain Tony's Saloon

“The Last Mango in Paris”

Key West, Florida USA
Cuisine style: None / Bar

Drank there in January 2016

By Sean Overpeck (CFE)

A landmark attraction and bar for Key West, Captain Tony’s Saloon is a must stop when your on the paradise island and the southernmost city in the United States. In its history the building used to be the city morgue, a cigar factory, bordello, a gay club, and later the Sloppy Joe's bar where Ernest Hemingway hung out from 1933 to 1939. Finally Captain Tony purchased it in 1958. A great place to stop in for a beer.

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From the saloon’s home page:

Favorite watering hole of such legends as Ernest Hemingway, Truman Capote, Tennessee Williams, Shel Silverstein and Jimmy Buffet, Captain Tony’s Saloon is not just a bar it is a piece of living history. The saloon’s namesake, fishing boat captain gunrunner, gambling casino operator and Mayor of Key West the late Captain Tony, was a larger than life character who was often described as a dropout from a Hemingway novel.

Originally built in 1851 as an icehouse that doubled as a morgue Captain Tony’s Saloon is steeped in history. When you stop in for a cold one, remember you are drinking where legends have been drinking for decades.

Main review:

I went down to Captain Tony's to get out of the heatWhen I heard a voice call out to me, "Son, come have a seat"I had to search my memory as I looked into those eyes Our lives change like the weather but a legend never dies He said, "I ate the last mango in Paris Took the last plane out of Saigon Took the first fast boat to China And Jimmy, there's still so much to be done.

From Jimmy Buffet’s “The Last Mango in Paris” released in June, 1985. Immortalizing the bar and Captain Tony Tarracino

If you're going to write an article about Captain Tony’s Saloon in Key West, then you need to start off with a little bit of Jimmy Buffet, especially when the “Last Mango in Paris” is about Captain Tony Tarracino to begin with. I first began listening to Jimmy buffet in my first year of high school back in 1989-90, though I can’t remember the first song I heard that turned me on to him, but I never looked back. I haven’t had the chance to this day to go to one of his concerts, but while in Key West in 1997, I did have a chance encounter with him at the Jimmy Buffet’s Margaritaville Bar.

We were on day three of our Key West trip and were exploring the North and western side of Duval Street plus Mallory Square, and like the Jimmy Buffet song we literally stopped in at Captain Tony’s to get out of the heat. The bar tender then said hello and asked us to take a seat. I can’t make this stuff up folks.

Outside the bar there is a large sign for the tourists to see showing that this bar used to be the hangout of Ernest Hemingway from 1933-1937. During that time the bar was named Sloppy Joe's, and owned by a friend of Hemingway named Joe Russell. In 1937 he purchased a building on Duval Street and moved Sloppy Joe's to that location over a rental dispute. The Building stayed either vacant or used as storage until the 1950s.

In 1958, Captain Tony Tarracino, a local charter boat captain, purchased the bar and renamed it Captain Tony’s Saloon. In the 1970s, Jimmy Buffett got his start in Key West and was often paid by Captain Tony with tequila for his performances.

The saloon was very typical to most Key West bars you will see when you come down to the island no matter if it is here, the Hogs Breath Saloon, on sloppy Joe's. You will see many interesting things cluttering the walls and ceilings. For Captain Tony’s it was dollar bills on one side of the bar, thousands of them. Then on the other side of the bar hanging by the hundreds were ladies bras and panties.

When we took a seat, the bar stools had different famous peoples names painted onto the top of each wooden seat, that represented a famous person that came to Captain Tony’s at one time or another. We got the seats of Dan Akroyd and John Candy.

We ordered some drinks, my fiancé with a wine, and for me a beer on tap, and when delivered, it was in a plastic souvenir cup, that you could also take out of the bar with you, as this area off of Mallory Square and Duval Street did not have any open container laws.

It was a fun visit and I’m glad I got to see it. As I did the research for this article, I had no idea that Jimmy buffet had made a song about it. The countless times I listened to “The Last Mango in Paris” it never dawned on me that the start of his song going down to Captain Tony’s represented this bar.

So many great wines in this world, here are a few of my favorite tastings:

Meerlust Wine Estate Rubicon Stellenbosch, South Africa	Hoopes Vineyard Napa, California, USA
Jonata Winery Santa Barbara, California, USA	La Motte Franschhoek, South Africa
Penner Ash Wine Cellars Willamette, Oregon	Yarra Yering Yarra Valley, Australia
Biltmore Estate Winery Asheville, North Carolina, USA	Bergström Wines Willamette, Oregon
Silver Oak Alexander Valley, California, USA	Eagles Nest Winery Constantia, South Africa
Ghost Block Vineyards Yountville, California	Pahlmeyer “Jayson Wines” Napa, California, USA

Other Key West reviews on Wine, Dine, and Play:

Ambrosia

Nine One Five

The Cork and Stogie

Key West Food and Wine Festival

Sloppy Joe’s Bar

Review basics:

Style:	Casual
Reservations:	Not Required Walk-Ins: Accepted
Dress code:	Casual
Cuisine style:	Worldwide Liquid
Experiences:	Lounge, Great bar, Rustic, Hole-in-the-wall, Tourist grabber, and a Neighborhood gem.
Payments:	Visa, MasterCard, Discover, American Express
Parking:	Street Parking
Wifi	The restaurants reviewed on this site may have Wi-Fi, but do not require you to go online, because the excitement of the food and wine alone will keep you too entertained instead of checking your social media and emails.
Noise level:	Loud
Smoking:	smoking and non smoking
Patio:	No

Restaurant address:

428 Greene St

Key West, Florida

33040

GPS Coordinates:

24.558804

-81.805508

Contact Information:

Maître d, Reservations:	+1 (305) 294-1838
Restaurant Website:	Captain Tony’s Saloon
Serving Hours: Eastern Standard Time (GMT - 5:00)	Mon-Sun: 10:00 am - 2:00 am
Groupon	Show me the Deals
Social Media & Accolades:	Facebook Link
Social Media & Accolades:	Pinterest