A Writing Retreat to Remember

A few months ago, I met 12 random people—total strangers—in a foreign country and hopped into an unmarked white van that took us to a remote location, only accessible by a narrow, winding dirt road with a cliff on one side, where we were to spend five days together in an 800-year-old Castello.

It sounds like the start of a thriller novel, but it was actually the start of the second Writer’s Digest retreat to Tuscany. The white vans were nimbly driven by kind men who successfully dodged scores of pedestrians darting into the streets as we left Florence. They safely got us to the Castello, which ended up being charming and picturesque. It featured a stunning view of the countryside and wisteria vines winding their way up the stone steps where we had “terrace time” each evening before sitting down to a home-cooked meal.

And the 12 strangers? They turned out to be delightful people dedicated to getting their stories down on paper and encouraging everyone else in the group that each other’s stories were worth telling. Collectively, we decided the word of the trip was validation.

Part of our time together was spent doing Ask Me Anything sessions. Rosecliff Literary founder and agent Jessica Berg and I answered all kinds of publishing questions, ranging from what editors do to how agents operate and why, and how to build your platform. We talked about craft topics and the pros and cons of traditional versus indie publishing. It was entirely tailored to the group of people on the trip.

Interspersed throughout were cooking classes, a visit to the top of the centuries old Castello bell tower and one-on-one discussions where we could talk with the writers about specific and personal details of their projects. To add an extra boost of inspiration, we took a day trip to Siena where people shopped, ate and drank, and wandered around a medieval city taking in the sights and sounds. We got to know each other in a way that can’t happen in a setting with larger groups of people.

It was an incredible trip, but don’t just take it from me. Here are some of the things our retreat participants had to say:

“This retreat was the perfect blend of being with other writers, enjoying the local culture, getting to see Florence and Siena, and having Amy and Jessica there to answer our writing questions. The food was wonderful. The friendships formed, I hope, will be life-lasting. … Any writer—unpublished, beginner or professional—will benefit from this retreat and time in Italy.” —Pamela C.

“I have attended several writing retreats. This one was exactly as it promised. The accommodations and planning were on point. The career advice was invaluable. The attendees were wonderful. The location was magical. Whether you are looking to kickstart or receive advice on your career, you will get it. I left recharged and knowing I am on the right track and was provided suggestions to explore to help my writing endeavors.” —Lisa W.

“I’m grateful for the experience. It combined a breathtaking setting with a unique learning opportunity. I’m invigorated and inspired!” —Chris B.

“The Writer's Digest retreat in Tuscany was dreamy. Do you want to sit under the Tuscan sun and write, maybe while sipping a glass of wine made on the property? You can do that. Do you want to make connections with other writers, perhaps while strolling the beautiful property and trails? You can do that, too. Do you want a chance to have-one on-one attention from two experts in the industry? Guess what? That's part of the retreat as well. I needed a break from my reality, I needed uninterrupted writing time, I needed opportunities to network and connect, I needed to learn more about the industry, and yes, I needed a glass of wine on the terrace. I got what I needed! You will, too!” —Aimee A.

“Warning: you will become addicted to writing retreats in Tuscany if you participate! Everything worked perfectly—writing time, feedback, food...” —Jenny N.

“I am changed after Florence. I am changed after Italy. I am changed after this writer's retreat. Whatever happens in America, whatever happens in the world, I now know humanity is safe in an artist's hands.” —Carmen C.

So, we are pleased to announce our 2027 WD Writing Retreat to Tuscany—registration is now open! Slated for April 11–18, 2027, we’ll start the trip in Florence, then head back to Tenuta di Spannocchia for another unforgettable retreat. Find out all the details and register for the trip here.