As the Southernmost point of the continental United States, the tiny island of Key West tends to become party central, especially during holidays and Spring Break. While watching the sun set from the dock at Mallory Square is tops on most visitor’s lists, there’s another time honored tradition that is almost as popular: the Duval Pub Crawl.

Duval at Night in Key West

Duval is the main street in what is known as Old Town Key West, and it runs north to south across the island. Mallory Square anchors the north end of Duval and is the best spot to start your evening’s pub crawl. Grab a margarita or a cold beer, find a spot that faces the water and enjoy the sunset.

Once the sun dips below the horizon, head on over to the Hogs Breath Saloon (400 Front Street, with a Duval entrance). If you haven’t eaten yet, and you can find a place to sit, then this is a good place to grab a bite. After all, you won’t last long on the pub crawl if you drink on an empty stomach.

Exit onto Duval and head south. When you reach Sunset Lane, about a block or so down, you’ll spot two of the watering holes that writer Ernest Hemingway used to frequent.

At the intersection sits Sloppy Joe’s, one of the most popular places on the island. They usually feature a live band playing covers and a small bit of empty space in front of the stage that serves as a dance floor.

Look to your right and about a half-block down, you’ll see Captain Tony’s Saloon. It’s a tiny shack-like building, but there’s usually somebody entertaining the drinkers with a guitar.

Once you’ve hit up both of these bars, you have to pace yourself for the next 2-3 blocks.
Read More »

Captain Tony's Saloon in Key West

In Key West, there are a lot of bars to belly up to. But not many have the colorful history of Captain Tony’s Saloon.

Located a half-block west of Duval St., the bright yellow building was built around the city’s “hanging tree,” where in the 1800s, convicted pirates were hung by vigilantes. The tree actually still exists within the building. Before becoming a bar, it housed a wireless telegraph station, a cigar factory and a bordello.

Following the end of prohibition, it was legally opened as a bar in 1933 and is the oldest licensed saloon in Florida. In the 1930s, it was the island’s original Sloppy Joe’s and served as one of writer Ernest Hemingway’s regular hang-outs.

In 1958, Captain Tony Tarracino bought the bar and it became Captain Tony’s Saloon.

Captain Tony's Interior Decor

The bar interior reflects its colorful heritage, with a decor that includes old licenses and ID cards glued to the wall and autographed bras dangling from the ceiling.

There is live music every night and on weekends, the bar tends to be packed with people. It’s just one of those classic dive bars where you sit and enjoy a few drinks with friends.

Captain Tony’s Saloon is located at 428 Green St in Key West. You can reach them at 305-294-1838.

[Photos by Michelle Snow]