Bull and Whistle Bar, Key West

The Bull and Whistle Bar is one of the oldest drinking establishments in the Old Town of Key West. Harking back to the seafaring days of yore, this bar is housed in a historic building from the early 1900s and has a distinct character and charm of its own.

Originally, the building served as a boarding house and later as a brothel, catering to the sailors and seamen who frequented Key West's busy port. In the 1920s, during Prohibition, it became a speakeasy and continued to operate as an underground bar for many years. During this time, the building was also used as a gambling den and a smuggler's hideout, making it a notorious spot in Key West's underworld. In the 1950s, the property was purchased by a local businessman and turned into a retail space. It remained in use as a store until the 1970s when a group of investors bought the place and converted it into a bar.

One of Bull and Whistle's unique features is its three-story layout. Each level has its own atmosphere, giving visitors a range of options, depending on their mood. The first floor – The Bull – is one of the few remaining open-air bars of Key West. This is a lively and casual space, with a long stretch of bar, table seating, and a small stage where local musicians perform nightly. Despite being open-air, they somehow managed to have hand-painted murals all around, which is quite visually stimulating.

The second floor, called The Whistle, has a more relaxed, casual atmosphere and features a large squared bar, pool tables, games, and a balcony with a great view of Duval Street, the main drag in Key West.

For those brave enough there's the third floor. Otherwise known as the Garden of Eden, this is a clothing-optional rooftop bar, which is much popular with the adventurous lot. The bar has made more than a few people blush, over the years, for when they say “clothing optional” they literally mean it. In addition to a few daring souls in their birthday suits, the Garden – described by Rolling Stone magazine as the "best-kept secret in Key West" – also gives you a bird's eye view of the island and body painting, among other things...

Apart from its unique layout, the Bull and Whistle Bar is known for its live music and entertainment. There are bands and performers playing almost every night of the week, and the atmosphere is always lively and fun. The range of drinks on offer is wide and includes local beers, craft cocktails, and frozen drinks, and there are often specials and happy hours to take advantage of.

It is always a good place to sit and pass the time sipping on a favorite beverage, enjoying live tunes, and watching people stroll by.