Captain Tony's Saloon

428 Greene Street
Key West, FL 33040
(305) 294-1838


Hours: 11:00 a.m. to Close
Location: Near the water
Drink: Pirates Punch
Eat: No
Music: 7 days a week
Parking: On the street, public lots
Boat Access: No
Unique Feature: The ceiling is lined with patron donated bras


Captain Tony's is a Florida beach bar so famous that Jimmy Buffet sings about it in "Last Mango in Paris." It was the original location of Sloppy Joe's. And it is here, the bar owners point out, that Hemingway spent time during the most productive years of his life. You'll find his original bar stool at Captain Tony's bar. 

The building that houses Captain Tony's was built in 1851 and was once an icehouse and it also doubled as a morgue. There is so much history in this little Florida beach bar. 

There is a hanging tree that grows right through the roof of this Florida beach bar. History says that pirates and criminals used to be hanged from this tree. 17 pirates, in fact, were hung from this tree by vigilantes. Captain Tony's is also said to be haunted. A haunted Florida beach bar. How cool is that? Papa Hemingway is probably still hanging out at this Florida beach bar and drinking his favorite Teachers scotch and soda. 

The late Captain Tony was such a popular bar owner that he was elected Mayor of Key West. He was a long time friend of Jimmy Buffet. In fact, we saw him at one of Jimmy's concerts in Tampa just before Captain Tony passed away. There is plenty of Captain Tony memorabilia hanging on the walls of this Florida beach bar. 

What first strikes you when you walk into Captain Tony's are the thousands of bras hanging from the ceiling. Women seem to give up their bras here. We never saw it happen in person, but given the wide variety of bras, it must be something to see. Mixed among the bras are business cards and license plates and the usual bar decor of dollar bills.

The bar features music seven days a week. I don't think we have ever been here when there hasn't been a band playing.