Literary Ghosts, Rebels of a Generation & Boozing in Havana with Hemingway

Word on the Street: Sherri Caldwell

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 Sherri Caldwell: author, journalist, teacher, world traveler, Mom to three, and Rebel Housewife extraordinaire. In this Word on the Street, Sherri dishes on the rise of the book nerd, literature as a travel guide, and the travel nightmare her family can’t ever forget.

1. You just published City Lights, Kerouac & North Beach Beats: A Literary Adventure. What is your Sidewalk about?

This Sidewalk is an exploration of the Beat Movement in San Francisco. We stroll through the fascinating history of North Beach, in search of the ghosts of Jack Kerouac, Allen Ginsberg and the friends, rebels, and madmen who launched a literary and cultural revolution with such lasting impact. In the 1950s, the Beats embraced all concepts of individual freedom and experimentation in art, spirituality, lifestyle, psychedelic drugs and sexuality. They were the precursors to the hippie generation of the ‘60s and the Summer of Love in nearby Haight-Ashbury. (Side note: I was born in 1967!)  

After WWII, San Francisco was still considered “the Wild West” and uncharted territory at the end of the world. How this group of free-spirited authors, writers and poets got themselves across the country to gather and establish themselves permanently in the staunchly Italian-American community of North Beach is the stuff of legend -- On The Road, literally. What better way to explore their haunts, bars, bookstores and hangouts than on a Sidewalk?

2. What is your favorite stop along your walk?

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City Lights Bookstore, without a question. On the Beat Trinity corner of Columbus & Broadway & Jack Kerouac Alley, this is a pilgrimage for book lovers visiting San Francisco. All of the other stops are preliminary and complementary, you really can take this Sidewalk in any order. Washington Square Park, Columbus Avenue, Caffe Trieste, the Jazz Mural and the Language of the Birds, the Beat Museum… they all relate, tie in, and ultimately lead back to City Lights and three historic and jam-packed levels of literary nirvana!

City Lights was co-founded in 1953 by poet and artist Lawrence Ferlinghetti, who fostered the Beat Movement in San Francisco by offering a hangout and meeting-place, publishing their works, and defending their freedom of speech.

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Although City Lights began as one tiny triangle storefront of the historic building, they gradually expanded into the neighboring shops and ultimately bought the entire building in 2001. Throughout the building, upstairs and down, there are all these little hideaways, fascinating nooks and crannies, and great places to hide away and read or soak up the history..

Walking downstairs into the basement was breathtaking. As the lore goes, in the early days, Ferlinghetti accidentally broke through the back wall of the shop and discovered a hidden basement. It turned out to be a secret storage room for the ceremonial dragon used in the Chinatown News Year’s parade. Ferlinghetti took over the space and put in the stairway. Previously, the basement had also been used by a  religious sect for a clandestine place of worship. You can still see all these weird quotations painted on the basement walls: “Remember Lot’s Wife” and “Born in Sin and Shapen in Niquity.”

3. What do you hope people absorb from going on your Sidewalk?

People on this walk will get a sense of history, and also a sense that cultural revolution can happen anytime. It’s all about activism and politics at places like City Lights. The rise of the book nerds and anti-conformists, baby!

4. You live in Atlanta. How did you get interested in creating a literary walk in San Francisco?

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I’m a book fanatic. To me it’s more interesting to search for the stories of a place than shopping or eating and drinking. Every time I go on a trip, I tend to go deep on local literature and history. Some people research a place by reading travel blogs, Yelp or Tripadvisor - I read the books. The more you know about a story, the characters and setting, the author and beyond-the-pages history of a place, the more immersed you become, as a traveler.

Last year, I taught a college literature course and introduced the Beat poem Howl by Allen Ginsberg, published by City Lights Publishing in 1956. Additional research led me to On the Road by Jack Kerouac, and I was hooked. Luckily I had an opportunity to tag along on a business trip to San Francisco earlier this year. With additional research, and many thanks to SFTravel, I spent my tourist time walking in the footsteps of the Beats in and around North Beach.

5. You must read a ton of books.

Hahaha. Yes. I coordinate the community book group and literary events in Midtown Atlanta for the business and civic association. I love it and I definitely read a lot!

In the early 2000’s there was a big push to increase the literacy rates in Atlanta. As a teacher and literacy advocate in the schools, I helped establish community reading programs. Barnes & Noble/Georgia Tech was an early sponsor, long-term partner and still supports our long-running Midtown Book Group.

6.  What inspired you to write The Rebel Housewife Rules?

When I had kids, I stopped working for a while. Almost immediately, there was a creative itch I needed to scratch. Writing was a big help to my sanity. I am originally from the West Coast (California & Washington State). Living in the South has been interesting - I’ve lived here for 25 years and raised 3 kids.

When I first moved to Georgia, everything felt so foreign to me and there were a number of hard-won lessons I learned. A friend and I started the Rebel Housewife blog to share a "survivor's’ guide to happily ever after." The book is women’s humor, a series of the Myths, Realities & Rebel Housewife Rules of marriage and motherhood aimed at down-to-earth, contemporary women who just want to live, love & laugh at some of the absurdities of modern life - very Erma Bombeck for the modern girls.

7. If you could travel with someone (dead or alive) to any city where would it be?

I’ve got a trip to Cuba coming up, so Ernest Hemingway is on my mind and reading list; although a tragic figure, he is one of my favorite writers.

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I would love to grab a barstool next to Hemingway at his favorite watering hole in Havana: El Floridita: “La Cuna del Daiquiri” (The Cradle of the Daiquiri). As Hemingway famously advised, “Don’t bother with churches, government buildings or city squares. If you want to know about a culture, spend a night in its bars.”

Hemingway enjoyed so many daiquiris at El Floridita, they concocted a special just for him, El Papa Doble - less sugar and double the rum. Two times more liquor to pack the most punch. (He was a big guy.)

After a couple Papa Dobles (or maybe just one for me), we’d head out on his fishing boat, the Pilar, for some deep-sea fishing and adventure. Of course, I would press him for stories and details about his colorful life in Cuba, just before the Castro Revolution in 1959. Was he really a spy for the CIA, and the KGB, too?

8. Hemingway was known to throw back a dozen Papa Dobles! Think you could match Hemingway drink for drink? No one wants to be sick on a vacation.

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I could not, would not attempt to match Hemingway drink for drink. Although it was not for that reason, that reminds me of an epic nightmare travel story, legendary in my family. Many years ago, we took two of our very young children on a trip to Seattle. Having gone to school in Washington State, we were excited to visit family and friends and take the kids to all the iconic spots: Pike Place Market, the Space Needle, the Seattle Science Center, Woodland Park Zoo...

We were staying at a very nice hotel downtown near the Space Needle, and the very first night of our trip, one of the kids woke us up, literally puking all over the bed. He was only about five years old at the time, so there was no alcohol involved, but it was a huge mess. Fortunately, we had two beds and a crib, so we moved him into our bed, but we had to call room service for a new set of sheets. At 2am…

It was some kind of stomach bug, and by the next morning, Dad was sick. Then Mom. Then the baby, of course. We could not leave the hotel room for two days. They kept bringing us new sheets, soda crackers and ginger ale. It was miserable. And we never got out to see the sights!

The story of “The Puke-y Hotel Room” trip to Seattle is legendary in our family!


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Corey Wood, Product Lead - Growth & Lifecycle

This interview has been condensed and edited.

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