Wine Dine and Play: May 2016

Sloppy Joe’s Bar

A Key West Tradition
Key West, Florida USA
Dined in January 2016

By Sean Overpeck (CFE)

Joe Russell is a household name when it comes to the famous people of Key West. He was a charter boat captain, rumrunner, Ernest Hemingway’s boat pilot, and the author’s fishing companion for twelve years. Key West was filled with free-thinkers who laughed at Prohibition, and on December 5, 1933–the day Prohibition was repealed, the city and people like joe went from operating illegal speakeasies to legitimate bars. When Joe opened his bar, it was named the Blind Pig, followed by the Silver Slipper and finally Hemingway who encouraged its name change to Sloppy Joe’s

Scroll down to read the main review, accolades and wine tasting notes

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From the bars home page:

The official beginning of Sloppy Joe’s Bar, the famous and infamous Key West saloon, was December 5, 1933–the day Prohibition was repealed. The bar was destined to go through two name changes and a sudden change of location before it would become Sloppy Joe’s, seen by millions of visitors to Florida’s southernmost outpost.

Key West being a bastion of free thinkers even in the thirties, Prohibition was looked on as an amusing exercise dreamed up by the government–and Joe Russell was just one of the enterprising individuals who operated illegal speakeasies. Even Ernest Hemingway, who made Key West his home at the time, slipped over to Russell’s on occasion to buy illicit bottles of Scotch, and the two struck up an enduring friendship.

Sloppy Joe s has been owned by the Snelgrove and Mayer families since September, 1978.
The building the main bar resides in was built in 1917, and its adjacent building that houses its kitchen and Joe s Tap Room was built it 1892. The two buildings together will be over 221 years old in 2016.

Main review:
After stopping in at Captain Tony’s where we had a drink, we walked around the corner to go into the new Sloppy Joe’s if you want to call it new since it has been there since 1937. The original location was at the bar we had just left from Captain Tony’s from 1933-1937. Joe Russell was having a dispute over the rent, so without missing a beat he purchased the Duval Street location for $2,500.00 and had his customers hold a glass of whisky or gin in one hand, and carry a bar stool in the other as they moved everything to the new location. The move happened in one day and he was never closed for business. Hemingway stayed at this location for two years drinking before leaving Key West for good, and dying in 1961. Unfortunately Joe died two years after his friend Hemingway left in 1941. 

Sloppy Joe’s is a huge and very crowded bar plus restaurant where you can see through a Live Webcam 24hrs a day. Their menu includes:

  • Key West Snacks
  • Pizza
  • Sandwiches
  • Other
  • Salads
  • Sides
  • Desserts
  • House Drinks
  • Wine
  • Draft Beers
  • Desserts

I still had a cup of beer with me from Captain Tony’s since Key West does not have any open container laws, so I ordered a Sloppy Joe’s Island Ale which was brought to me in a souvenir cup like the one I had from Tony’s. A perfect picture for two bars that were once one and the same. My fiancé had one of the house specials called the Key West Lemonade Skyy Citrus Vodka, sweet & sour, cranberry juice and splash of 7-Up. It was one of 20 special drinks they had along with other colorful cocktails like Speakeasy Punch, Frozen Pain in the Ass, and the Sloppy Rita.

We were also getting hungry and didn’t want to wait for the next event that we had tickets for as part of the Key West Food and Wine Festival called Duval Uncorked. So we looked over the menu, and since I had never tried a Conch which is a local island delicacy or a snail. So from the snacks menu I tried the conch fritters served with a key lime mustard sauce. Thank god for the sauce because it was a pretty bland dish. I’m not sure if that is common to just this menu or all menus. 

Other items on the snack menu included your basic treats like fried calamari, cheese sticks, onion rings, nachos, and Colombian Arepas  to name a few. My fiancé ordered the Sloppy Fries from the side menu to munch on. They were topped with Sloppy Joe’s meat sauce, cheddar, and jack cheeses. 

It was a fun experience, and I’m glad we got the chance to stop in and see the history of the bar, even though it looked like a modern island bar, and if you don’t know the history or no one tells you, it would pass off as just another bar in the islands.

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5 stars
 is Extraordinary
4 Stars
 is Outstanding
3 Stars
Exceeded Expectations
2 Stars
is Above the Average
1 Star
is an Average Dining Experience
No Star Rating
The Restaurant is Basic, Poor, or Appalling

Overall Star rating by Wine, Dine, & Play:
1 of 5
4  of 10
Quality of the Food:
5  of 10
Plate Presentation:
4  of 10
Customer Service:
6  of 10
Wow Factor:
4  of 10
Wine Selection:
 (See the full list under the review basics section below)
1 of 10

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

Food Prices 
(excluding, alcohol, taxes & gratuity)
$£€¥ -                Under 50.00 
$£€¥ x 2 -          51.00- 99.00 
$£€¥ x 3 -          Over 100.00 
$£€¥ x 4 -          Over 200.00 
$£€¥ x 5 -          Over 400.00 

**Currencies chosen reflect the world’s major travelers and restaurant connoisseur’s**

My food bill:
Price chart:
United States Dollar (USD)
Australian Dollar (AUS)
Great Britain Pound Sterling (GBP)
Canadian Dollar (CAN)
Chinese Yuan (CNY)  
European Union (EUR)

Alcohol Prices:


Customary starting gratuity for restaurants in the United States begins at 15% 
Of your total bill and increases based on the level of service you received. 
In Europe, Australia, Africa, and some Asian countries it is not 
common to leave any gratuity as it is already included into 
the check, but you may feel free to leave extra anyway


Review basics: 
Wine selections by region:

1 of 10

Old world: 

  1. Italy:
  2. Germany:

New World: 
  1. California:

Corkage fee’s:
The Restaurant does not list any corkage fee’s however, most American restaurants charge $25.00 per bottle
Restaurant style:
Not Required
Dress code:
Very Casual
Child policy:

The Restaurants reviewed on this site may have a child’s menu or cater to them; however for full enjoyment of food and wine, it is recommended for children not to be in attendance, unless they have been trained in proper etiquette
Hire a Babysitter. 
Cuisine style:
Seafood, American, Southern, & Vegetarian
Hot spot, Great bar,, Rustic,, Hole-in-the-wall, Tourist grabber, and a Neighborhood gem
Visa, MasterCard, Discover, American Express
Street Parking
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 to WHAT!!!?
Nonsmoking restaurant

Restaurant address:
201 Duval Street, 
Key West, FL 

GPS Coordinates: 

Contact Information: 

+1 (305) 294-5717
Restaurant Website:
Serving Hours:
Eastern Standard Time (GMT - 5:00)
Daily: 9:00 am - 4:00 am
Sunday: Noon - 4:00 am


Social Media 

Facebook Link                

Reviewed by:
Sean Overpeck (CFE)
Picture below was taken in Sydney Australia in March 2015
While dining at Quay

About Sean:

I am based out of St. Petersburg, Florida working in the food service industry for the past twenty years, and am currently with the American Embassy as the Executive Chef in Basra, Iraq. Formally I have worked with groups contracting in Afghanistan, Dubai, and Antarctica, also working in restaurants in and around Atlanta prior to the wars. I have also owned a catering company and served proudly in the United States Army Food Service Program. The idea for the Wine, Dine, and Play started in late 2012 after a trip to Jordan, when I was asked by friends to write down the experiences from a few Jordanian restaurants, plus the wine from the region that I tasted, and locations of interest such as Petra, and the culture. Since that time, over 200 articles have been written on restaurants, including fifteen from the worlds top 100 lists of San Pellegrino and the Elite Travelers Guide; exotic world locations such as Dubai, Petra, Victoria Falls, and South African Safari’s; food recipes & Grand Food Dictionaries; country cuisines such as Afghan and Peruvian; and of course wine from vineyards in California, Oregon, the Carolina’s, South Africa, New Zealand, and Australia

Who is John Galt?

“Culinary perfection consists not in doing extraordinary things, 
But in doing ordinary things extraordinarily well.”
-Angelique Arnauld (1591-1661)

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