Duval Street, Key West (must see)

Duval Street is the most famous and most traveled street in all of Key West. Designated a "Great Street" in 2012 by the American Planning Association, it runs north-south through the entire length of the island, from the Gulf of Mexico to the Atlantic Ocean, and is the main thoroughfare of the city, renowned for its vibrant nightlife, historic buildings, and an array of unique shops and restaurants.

The street is named after William Pope Duval, the first territorial governor of Florida. It was originally a sandy path that linked Fort Zachary Taylor (in the south) to Mallory Square (in the north). As the city grew, more businesses were established on the street, and thus it became a bustling commercial hub.

In the 1800s, Duval Street was home to many of Key West's wealthiest residents. The street was lined with elegant mansions, many of which have been preserved and turned into museums or bed-and-breakfasts. During the early 20th century, it grew popular with sailors and fishermen, who frequented the numerous local eateries and watering holes.

The north (lower) end of Duval (or “wild” side) accommodates the majority of bars and tourist attractions and is where most of the carousing takes place until all hours of the night (and early morning!). The south (upper) end of Duval (the "quiet" side) houses the Southernmost Point, with a mix of early Key West Victorian mansions and bungalows dotting the neighborhood. Although it is more residential and less filled with tourists, the sidewalks still bustle with activity due to the art galleries, boutiques, inns, and bodegas lining them.

On Duval Street, you will find the famous Sloppy Joe's Bar, which used to be a favorite haunt of writer Ernest Hemingway. The street is also known for its colorful characters and street performers, such as the "Cat Man" (performing with his trained cats), and the annual Fantasy Fest celebration, a 10-day event featuring costume contests, street parties, and other festivities.

Overall, Duval Street offers a unique blend of history, culture, and entertainment, and is a must-see destination for anyone visiting Key West.