Every major city in the world has that neighborhood: the one that’s a little rough around the edges, that has the interesting characters, and that the guide books might tell you that you can skip. But sometimes these places can also have the most interesting histories, offer great insights into the way that a city came to be, and introduce you to a side with more local flair than you’ll find on the beaten tourist path.

Just like the rest of the City by the Bay, these few blocks are steeped in a colorful history filled with equal smatterings of optimism, rule-bending and activism. Its past is rife with speakeasies, theaters, jazz clubs and a seemingly endless influx of immigrants throughout the past century, the Tenderloin embodies some of San Francisco’s richest history. Today, this island in SF’s growing sea of gentrification has become easy to misunderstand; its glory days often feel as if they’ve faded into the past. But hidden in the secret corners of the Tenderloin are an endless array of local gems that are worth visiting and will foster a greater appreciation for this vibrant neighborhood.

There are many places to visit here that are of historical and cultural significance; the Tenderloin Museum is the best place to go to find out more, but this website highlights a selection of some of my personal favorites, from histroric landmarks to venues that have popped up more recently in an effort to improve the community.