Harlots, Hooch & History in Old San Francisco with Duggan McDonnell

San Francisco, CA

  • The Cherry Bomb
  • A glance down Gold St. Photo: Geri Koeppel.
  • The Transamerica Pyramid overlooks the old warehouses of Jackson Square.
  • Inspecting the plaque on the Hotaling Building.
  • The Pisco Punch

1 hour and 45 minutes
0.3 mi
Guided by Duggan
Duggan McDonnell


Join me on a walk of the Barbary Coast (and the Devil's Acre) where the whiskey drowned, women seduced and fires raged! San Francisco, born from a womb of gold, came into the world as a celebratory, multi-cultural, altogether combustible boomtown. There's no better way to experience the Gold Rush days then through its elixirs and stories, exploring the alleys, saloons and tasty cocktails of yesteryear.

About Your Guide

Duggan McDonnell has been a barkeeper, distiller, winemaker, educator, community organizer and is the author of "Drinking the Devil's Acre: A Love Letter from San Francisco and her Cocktails." McDonnell was named a 'Leader of the American Cocktail Revolution' by Food & Wine magazine. A true champion of the cocktail, Duggan has taught at the Culinary Institute of America at Greystone, Tales of the Cocktail in New Orleans, and for the United States Bartenders' Guild. He is happily employed by Pernod Ricard USA, and lives in San Francisco, California.

Go on this Sidewalk

Guide Points

  1. The Old Ship Saloon

    This is the oldest bar in the city, established in 1851. Then, the Old Ship Saloon was a saloon built into an abandoned boat.

  2. Gold Street

    In the early days, this was what a typical street in San Francisco looked like: narrow in width and walls holding mini canyons.

  3. Hotaling Place

    The first building on the left, at the intersection of Jackson St and Hotaling Pl is the first of three special sites we'll visit today. To…

  4. Taverna Aventine

    This little cocktail lounge & restaurant sits on the original retaining wall of the city. Head inside, and take in its history.

  5. Comstock Saloon

    Comstock Saloon is renowned for its delish cocktails - it also boasts hundred-year old roots. The building itself was home of the oldest ba…

  6. City Lights Booksellers & Publishers

    I'd be remiss to walk past City Lights and not at least mention the historic gravitas of this bookstore.

  7. The Saloon

    The Saloon also claims to be the oldest bar in the city, and it smells like it. It opened in 1861 and not much has changed.

About Sidewalk

Sidewalk is an app that provides free, guided walk experiences that can be created by anyone with stories to share about places they know and love.

The app navigates people through a neighborhood walk using GPS turn-by-turn directions, rich imagery and storytelling.