Wayfaring Writers

Valparaiso, Chile, December 1-10, 2023
ItinerarySign Up

Are you craving adventure? Would you love to learn how to hone your writerly skills of observation and your ability to make your travel writing pop off the page?

Come explore the world…

In December 2023, Wayfaring Writers is headed to Valparaiso, Chile, for a writing adventure!

Travel is the best thing we know to spark your adventurous spirit and inspire creativity. And travel WRITING offers opportunities to be inspired by PLACE and CHARACTER like nothing else.

The retreat is a rare opportunity for a small group of writers to immerse themselves in their craft while experiencing the food, drink, art, and history of Chile. We’ll revel in the ancient architecture, stroll through bustling markets, experience culinary adventures, and enjoy panoramic views from lofty lookout points.

Join Wayfaring Writers in Valparaiso, Chile, and you’ll have the adventure of a lifetime AND get to write about it for publication. We’ll make sure your writing shines with as much color as the city we’re traveling to.

“Let the world change you and you can change the world.” —Che Guevera, The Motorcycle Diaries

Tentative Itinerary


  • Travel to Santiago, Chile
    Get settled and catch up on sleep.
    No-host dinner or we cook together.


  • Morning – Bus to Valparaiso, Chile
  • Afternoon – Lunch at The Winebox.
    Meeting and orientation for the next 5 days.
  • Evening – No-host dinner together


  • Morning – Class: (Cami/Lisa) What great travel writing does and doesn’t do. Assignment: Have an adventure with a universal takeaway.
  • Writing time / Lunch
  • Afternoon – Walking tour of Valparaiso
  • No-host dinner
  • Gather for reading in the evening


  • Morning – Class: Character Study. Writing as stealing. Assignment/prompt: Meet someone, turn them into a character, tell their story.
  • Writing time / Lunch
  • Afternoon – Tour Pablo Neruda’s house and then a discussion on the patio at The Winebox on Neruda and Character
  • Evening – No-host dinner then wine and open mic


  • Morning – Class: Place. Now that we’ve soaked up the city… How do we write about a place to really make it come alive?
  • Writing time
  • Lunch
  • Afternoon – Funiculars
  • No-host dinner
  • Evening – Wine tasting on the roof


“I feel about travel the way a happy new mother feels about her impossible, colicky, restless newborn baby – I just don’t care what it puts me through. Because I adore it. Because it’s mine. Because it looks exactly like me.” —Elizabeth Gilbert, Eat, Pray, Love


  • Morning – Class: (Lisa) How to watch for off-the-beaten track experience you’ll be able to write about.
  • Writing time
  • Lunch
  • Vina del mar for a walk and no-host dinner on the beach
  • Evening – Wine and reading


  • Morning – Meeting for next steps.
  • Free day in Valparaiso
  • Evening – pack up
  • Dinner together at The Winebox


  • Morning – Bus back to Santiago and get settled at the hotel
  • Lunch / Writing time
  • Afternoon – Class: How to integrate history into your storytelling
  • Afternoon trip to the Virgen
  • No-host dinner
  • Gather for a night on the town


  • Morning/afternoon – Tour of Santiago
  • Dinner together
  • Evening – Closing

DAY 10

  • Travel Home

Join an upcoming Info Session…

(Details Coming Soon)

Email info@wayfaringwriters.com for more information!


Craft Talks: On class days, we’ll hold craft talks in the mornings and then give you the afternoon to write and explore on your own. Topics will include watching for off-the-beaten-track experiences, what great travel writing does and doesn’t do, character study, writing about place, integrating history into your storytelling.

Tours: On tour days, we’ll explore the art, history, culture, food, and natural beauty of Valparaiso.

Retreat Cost: $4,497 until June 30 / $5,497 starting July 1.

Space is limited to 7 (seven) participants.

Is your spouse or partner jealous? Why not bring them along. For $2,497 a partner can participate in all tours and have free time during writing events and hosted dinners.

What’s included in the cost…

  • Pre-trip preparation class
  • Nine (9) nights accommodation in Valparaiso, Mexico
  • Breakfast every day, Lunch on tour days,
    Dinners on three nights with industry experts
  • Tour, transportation, and entrance fees – all scheduled adventures are totally on us!
  • Walking tour of Valparaiso
  • Books that incorporate travel writing
  • Publication in an anthology

What’s NOT included…

  • Your roundtrip airfare from home
  • Hotel transfers
  • Personal shopping/souvenirs, personal phone calls, taxis, laundry
  • Meals on no-host days
  • Tips and gratuities
  • Personal, medical, or trip cancellation insurance

Your Hosts…

Cami Ostman

Owner of The Narrative Project and co-founder of Wayfaring Writers

Cami Ostman

Cami Ostman has traveled to all seven continents and to twenty-four countries. She’s run 25 marathons and zillions of races of other distances, always at the back of the pack. She is the author of Second Wind: One Woman’s Midlife Quest to Run Seven Marathons on Seven Continents and co-editor of Beyond Belief: The Secret Lives of Women in Extreme Religion (Seal Press). Cami holds a Bachelor’s of Education in English and Theater from Western Washington University and a Master’s of Science in Marriage and Family Therapy from Seattle Pacific University. She has a special interest in helping women live more authentically and freely. She is also a dog lover, a wine connoisseur, a runner, and a blogger. She runs a program for writers called The Narrative Project and has a passion for changing unhelpful narratives so people can be in charge of her own stories. She coaches people into their truest expression of themselves. Cami lives in Seattle, Washington.

Lisa Dailey

Owner of Silent Sidekick and Sidekick Press and co-founder of Wayfaring Writers

Lisa Dailey

Lisa Dailey is an avid traveler and writer. In 2015, she traveled around the world with her husband and two teenage sons visiting 14 countries and nearly 100 locations. In her time abroad, she unearthed new ways of looking at her life through her discoveries in remote corners of the world and she continues to enrich her life through travel. Lisa is a voracious reader and writer, and has published more than 20 titles and 200 authors at her company, Sidekick Press, including her own travel memoir, Square Up. A native Montanan, Lisa now makes her home by the ocean in Bellingham, Washington, but returns to her roots every summer for a healthy dose of mountains and Big Sky.

Special Guests…

Laura Mazer

Wendy Sherman Associates

Laura Mazer

Laura Mazer specializes in adult nonfiction with a focus on women’s issues, intelligent pop culture, counterintuitive self-help, packaged gift or “concept” books, and books that take us on geeky deep dives into fascinating facets of everyday life. She adores history, biography, and celebrations of literary legacies, especially when they offer fresh stories about women. She also represents select upmarket fiction.

Before joining Wendy Sherman Associates, Laura was executive editor of Seal Press, an imprint of the Hachette Book Group, where she edited bold voices in adult nonfiction. Her New York Times bestselling books include So You Want to Talk About Race by Ijeoma Oluo and From Cradle to Stage: Stories from the Mothers Who Rocked and Raised Rock Stars by Virginia Grohl. Previously, Laura was the managing editor of Counterpoint and executive editor of its imprint Soft Skull Press, where she acquired literary and upmarket fiction and narrative nonfiction.

Before joining the book publishing industry, Laura was managing editor of the global news agency representing some of the most influential opinion writers and editorial cartoonists of the day, including Hillary Clinton, Arianna Huffington, Molly Ivins, Ann Landers, and Mike Luckovich. A longtime advocate for underrepresented voices, Laura sits on the board of The OpEd Project and teaches publishing workshops for Bold Voice Collaborative.

What are you waiting for?


Please fill out the application below. Once reviewed, we will send you a link to pay a $500 non-refundable deposit to reserve your spot!

This retreat is limited to 7 (seven) participants MAX. The pre-trip group call will be announced by September 1, 2023 and will be recorded.

Not sure if this trip is for you?

Please make an appointment to chat with Lisa here.

Cancellation Policy

We reserve the right to cancel the trip if it does not meet the trip minimum. If we do so, your deposit is refunded in full. For a full description of our cancellation policy, see terms and conditions.

Can you comfortably walk up to 5 miles per day?

Do you have any dietary restrictions?