Whiskey Warehouses, Drinking Contests with Grizzlies & the Downside of Traveling with Mark Twain

In each edition of “Word on the Street,” we interview a Guide to learn about their Sidewalk and some of their best travel stories.


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Meet Duggan McDonnell, the acclaimed author of "Drinking the Devil's Acre: A Love Letter from San Francisco and her Cocktails" and Guide of “Harlots, Hooch & History in Old San Francisco.” He gushes on his favorite cocktail city, his worst travel experience and the needs of the “Urban Sophisticate.”

1. You just published Harlots, Hooch & History in Old San Francisco. What is your Sidewalk about?

“Harlots, Hooch and History” gets to the sinful center – the root – of historic San Francisco. My Sidewalk is a stroll of historic drinking establishments of the Barbary Coast.

2. What was the Barbary Coast like back in the 19th century?

The Barbary Coast was one of a kind – exciting, intoxicating, frightening. You could have a drinking contest with a grizzly bear – and win! There’s never been a place like it in the world before or since. Love it, or forget it, don’t come to San Francisco and miss out on a taste of what was the Barbary Coast.

 Men standing outside a Bryant Street saloon, Photo: SF Public Library

Men standing outside a Bryant Street saloon, Photo: SF Public Library

3. What do you hope people get out of going on your Sidewalk?

This geography of San Francisco is laden with history. Experiencing it on foot (and on barstool!) makes for an absolutely amazing afternoon. Physically walking a path through a neighborhood is a better way to experience a city’s soul.

4. What is your favorite stop on your Sidewalk and why?

The Sidewalk meanders its way to Hotaling Place – one of my favorite streets in the city. It marks the dividing wall where the Pacific Ocean originally met the shoreline of San Francisco. Run your hands along the stone walls of the A.P. Hotaling warehouse.

This building stored all of the whiskey, port, madeira, and rum of San Francisco. It is interesting for me, as a booze guy, just how important that location was, and how big the building is. Civilization on the West Coast started right here!

And the best part: the Hotaling warehouse was one of three buildings that firefighters saved during the fire in 1906 caused by the great earthquake. Read the limerick on the plaque affixed to the warehouse wall, it explains everything:

If, as they say, God spanked the town / For being over-frisky, / Why did He burn His churches down / And spare Hotaling’s whiskey?

5. What city’s cocktail scene impresses you?

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Buenos Aires has a sophisticated cocktail scene that has existed since the city’s early days. 80 years ago, the Branca family (the Italian makers of the bitter herbal liqueur, Fernet) built a distillery in Buenos Aires because Argentinians were drinking so much of it.

There are some incredible historic bars and cafes with an Old World vibe – drinking is alive, yet rarely messy. Also, you can smell the dust of paper in the air as Buenos Aires is the most literate city in the world, chock-a-block with bookstores.

6. Sounds like you would be happy spending more time in Buenos Aires.

I could live there. It has all the things that an Urban Sophisticate could want. Beautiful streets, killer art, amazing food, drink. And yet it still feels casual and affordable. The Recoleta neighborhood feels like Pacific Heights [San Francisco neighborhood with turn-of- the-century mansions] meets Paris.

Buenos Aires is a great mix of casual culture and yet stylish at the same time. And it is warm. Perhaps my favorite city in the world.

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7. Tell me a travel nightmare story that you have survived.

My wife and I were taking a ferry from Buenos Aires, Argentina to Colonia, Uruguay over the Rio de la Plata. There’s a lot of wind out there, and this day was stormy. Beyond choppy. That boat ride was the gnarliest half hour of my life.

The ferry picked up speed, and started crashing through the waves, getting beat back every time. Passengers were literally being thrown out of their seats. The storm picked up, the waves got larger, and the captain drove head on, attacking each violent wave as the boat smashed through a crest and then plunged to the trough.

My stomach wasn’t having it: I stumbled to the bathroom only to discover other passengers had preceded me. And no one had bothered to aim! - The floor was slick in vomit, sliding all over. I held my breath, closed the door. In that moment, I decided to stay calm. I returned to my seat, and found my wife in a quazi-fetal position and promised her that the bathroom wasn’t worth the trip.

A minute later, it started: the frantic rustling of tiny wax-lined bags. A husky man from the back on the left hand side. A set of kids near the front. All around us – retching. Everyone, except me, was throwing up. The sound grew louder, a staccato chorus of heaving. Still, we crashed forward, still, kids fell out of seats.

Suddenly, from nowhere, a song rose over the loudspeakers: Celine Dion’s, My Heart Will Go On. You’re fucking me?! I said. The Titanic song! I figured the captain of that ferry has a wicked sense of humor… It broke the spell, and we started laughing. Barfing, and laughing.

To this day, I think twice before stepping foot on a boat.

8. If you could travel with someone, alive or dead, to any city, who would it be? 

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When you travel with someone, you learn things. I wouldn’t want to travel with a writer that I admire because you just know that person would be a cantankerous SOB. Mark Twain would be the worst person to travel with.

But Tom Sawyer, the character, I’d go with him. He’d be hilarious. Every minute would be a vacation. He would cause trouble and then be charming. Who wouldn’t want to travel with someone who turns the chore of fence painting into a hoot?


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You can learn more about Duggan by checking out his website and Instagram. If you're looking to get a history lesson with a buzz, Drinking the Devil's Acre is your jam.


Interview has been condensed and edited.

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