Writing It Real in Tuscany

DATES: 06/01/2024 - 06/08/2024
LOCATION: Tuscany, San Giovanni d'Asso
PRICE: $2,975.00

Sheila Bender is the founder of Writing It Real, an online community and resource center for those who write from personal experience. Her most recent books are the poetry collection, Since Then: Poems and Short Prose (nominated for the Washington State Book award), Behind Us The Way Grows Wider: Collected Poems 1980 – 2013, the prose memoir, A New Theology Turning to Poetry in a Time of Grief, and Writing Personal Essays: Shaping and Sharing Your Personal Experience among others.

Sheila received a Master’s in Creative Writing from the University of Washington and since then has committed much of her career to facilitating others in writing to the essence in many genres including flash fiction/nonfiction, poetry, memoir, and personal essay.

She is a past Distinguished Guest Lecturer at Seattle University and for five+ years hosted the KPTZ.org radio program “In Conversation: Discussions on Writing and the Writing Life.” You can listen to the programs as podcasts archived on Writingitreal.com – <https://writingitreal.com/article-archives/audio>.

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Currently, Sheila is a regular instructor for The Writer’s Workshoppe in Port Townsend, WA and continues to teach online for Il Chiostro, Women on Writing and the International Association for Journal Writing as well as through her website WritingItReal.com.

Here are 2 recent interviews from her KPTZ.org radio program “In Conversation: Discussions on Writing and the Writing Life”:



Practicing Creative Nonfiction, Poetry and Fiction Strategies for Writing the Essence

If you’ve wanted to travel to Italy with a group of like-minded writing enthusiasts (all levels of experience and publications welcome!), our spring writer’s workshop in Tuscany is a wonderful opportunity. During seven days in Italy, you’ll enjoy morning and evening writing workshops and readings, afternoon excursions with time to wander and write, and one-on-one writing consults with instructor Sheila Bender.

Gathering inspiration from arriving in Florence, from the landscape around the noble villa you’ll be housed in, from the aura of nearby villages, not to mention the delicious food and wine served by our personal chef, you’ll write new work, expand older work you bring with you, and gather the responses of trusted listeners.

Bring your laptop, tablet or just pen and paper, along with curiosity about sub-genres new to you and an appetite for Italian vistas. You are guaranteed to come away enchanted, unblocked on writing that has been troubling you, and loaded with new work.

My week at Il Chiostro in breathtaking Tuscany, learning, writing, sharing, bonding, and touring was a joyous gift  that I gave to myself. Every moment was as delicious as each morsel of Italian food and glass of wine.  Staff Michael and Linda are two of the most gracious hosts I have ever met, while teacher Sheila herself is a gift.  Cheers to all lucky enough to enjoy this unique experience next spring! — Nancy Smiler Levinson, 2019 (with permission)

Podcasts, publications and Interviews:

Pantoum from Northern Jutland, poem published in the British journal called The Lake

Author Magazine Interview
Sheila interviewed by Mark Matousek
Sheila on Writing the Personal Essay

The view from our terrace at the villa in San Giovanni d’Asso

Lunch on the terrace

Meals and our “Home”  Dinners are prepared by our personal chef using local and seasonal ingredients to make every meal a feast!  We’ll eat together in the dining room each evening.  Breakfast is served buffet-style.  You are free to eat indoors, out on the terrace or in the garden – or go to town to enjoy a cappuccino with the locals! There is a lovely private pool at the end of the garden which makes for the perfect end to a long day writing. The villa is across the street from a historic castle and within easy walking distance of the town where there is a grocery store, cafe, restaurant and even a weekly outdoor green market.  You can easily be independent to meet and interact with the locals.

Il Chiostro was a wonderful slice of time out of time in Tuscany. Michael & Linda were terrific hosts and created a perfect backdrop for Sheila’s marvelous workshop. Sheila is an exceptionally gifted teacher with a deep talent for listening, critiquing and creating a sense of community and trust with the participants.  I have taken another workshop with her since and have signed up for two more, one of which is an online extension of our writing workshops. The bonds between us were that strong that something of a community was formed.   The villa was comfortable, the meals delicious and convivial. The day trips were a lovely taste of Tuscany.  The Tuscan workshop was a great springboard for what I think will be many more workshops. Sheila is a wonderful mentor.  Lee Ali, 2019

Writers from 2017 workshop in Lake Garda

Other Activities:

  • excursions to the medieval towns of Pienza and Montalcino
  • introduction to truffle hunting traditions
  • optional local winery tour
  • visit to nearby botanical gardens Il Bosco della Ragnaia created by an artist who turned his talents from painting and sculpture to designing and maintaining this beautiful space


I spent a glorious week writing, eating and walking around the beautiful village off San Giovanni d’Asso.   We lived in a wonderful villa and were shepherded to nearby towns by our hosts Michael and Linda.   I can’t imagine more amiable, capable hosts than Linda (the divine chef) and Michael nor a more empathetic and talented writing teacher than Sheila Bender.  It couldn’t have been better!!! — LR, 2019

Price: $2,975 p/p; non-writers $2,675

Optional supplement:  $475 for single room, limited availability

$500 deposit due upon registration.  Balance due by April 15, 2024.


  • Shared double room with private bathroom in villa (single room available for a supplement)
  • Daily traditional breakfast and dinner, (including wine) prepared by our personal chef
  • Daily writing classes and critiques with Sheila
  • Excursions to nearby towns like Montalcino and Pienza
  • Transportation and guide for all local excursions
  • Pick up from Florence train station at 3:30pm on arrival Saturday
  • Transfer to train station in Buonconvento on final day (not Florence) for connections to Rome, Florence or beyond

Does Not Include:

  • Airfare
  • Gratuities
  • Independent meals and sight-seeing

To Register:  just click on the Sign Up Now button.  A non-refundable deposit of $500 is required to secure your spot in the workshop.  Payment can be made on line with a credit card, or you can follow the instructions to send in your registration and payment by mail.  Once we receive your deposit we will send you a formal Registration Confirmation with further information about the program.  You will receive 2-3 other correspondences by email prior to the workshop with information about Italy, a supplies list and an electronic invoice for the balance.  Final Balance is due by April 15th.  Any time prior to your arrival, if you have questions about anything regarding the trip or the program, you can contact us by email or phone and we’ll be happy to assist you.

Contact us for more information: info@ilchiostro.com or speak to us live at 800-990-3506.

San Giovanni d’Asso

SAN_GIOVANNI_D'ASSO-Gilbert RiosWhere We’ll Stay: This is part of our new Il Chiostro Nobile series. We will be hosted for a week in an authentic, elegantly appointed villa that was at one time home to a noble Italian family. The palazzo includes a formal garden, private swimming pool with inspiring vistas. Inside there are 8 twin, double or single bedrooms in the villa, each with a private bathroom. The rooms are decorated in authentic, elegant family antiques.

Common spaces include 2 elegant living rooms, a terrace overlooking the garden, large fireplace, kitchen and formal dining room.

The villa is across the street from a castle and within easy walking distance of the small town.  You can easily be independent to meet and interact with the locals.

The villa from the garden

The Villa: a 13th century manor house situated on a hillside in a small town with views of the Val d’Orcia. Owned by the current family for 102 years, it was gracefully restored in the 19th century with comfortable period furnishings. The rooms are bright and airy with high ceilings and beautiful views out to the gardens and the valley beyond. Bedrooms are elegantly appointed each with a private, modern bathroom. Because we will be the exclusive residents at the villa during the program, the experience will be intimate, like living in our own Italian mansion. Our meals will be shared in the formal dining room, on the terrace or in the garden. All living quarters of the villa are on the second floor, accessible only via a staircase.

Dinner table
Dining Room and Living Room in the Villa

View from our window, photo by Linda Mironti

The Grounds: the setting is extraordinary overlooking the valley towards the Brunello wine country. There is a formal garden with a pool, lounge chairs, a shade arbor and plenty of seating for outdoor meals. The Villa is an easy walk through the facing castle (now the museum of truffles) to the quiet village of San Giovanni d’Asso.
The villa and grounds consist of:

  • 8 twin or double bedrooms, each with bathroom either ensuite or next door.
  • A dining room and breakfast area
  • Large terrace with tables
  • 2 sitting rooms
  • Wi-fi internet access
  • Heat or air conditioning as necessary
  • A large private formal garden area with fountains and, seating area
  • A private pool at garden edge with a valley view
  • There is a changing room near the pool with WC
  • Air conditioning or ceiling fans in bedrooms
  • Very quiet setting in small village

SGA-Bathroom2 SGA-Bedroom3
Double bedroom and bathroom

SGA-Bedroom Twin2Twin bedroom

The Town: San Giovanni d’Asso is in the Siena section of Tuscany. It is famous throughout Italy for its production of truffles. Small and quiet with fewer than 1,000 residents, the town has a café, grocery store, 2 restaurants, several historic churches and a weekly outdoor market. A very special addition is the beautiful botanical gardens “Il Bosco della Ragnaia” (http://www.laragnaia.com/EN/) created by an artist who chose to turn his talents from painting and sculpture to designing and maintaining this beautiful space that is open free to the public.

The Area: San Giovanni d’Asso is 30 km southeast of Siena in the area known as the Crete Senese (see photo below). Pienza and Montalcino and the famous Brunello wine country are easy day trips.

Garden View-Gilbert Rios-sm

Garden View by Gilbert Rios


Florence will be our meeting point on the first day of the workshop. A van will pick up the group at the train station at about 3:30 pm on Saturday afternoon.

Above the Ponte Vecchio, photo by Andy Holtzman

We recommend that you fly into either Florence, Pisa or Rome (Milan is a bit too far away). Florence is closer but it doesn`t have an intercontinental airport, so there are no direct flights from the US. You would have to change planes in a larger European city. From the Florence airport you must take a shuttle bus (Volainbus) into the center (20 minutes).  

There are more scheduled flights from the US to Rome, many of them direct. From Rome, you will need to take a train to Florence (about 2 1/2 hours).

Important! In making your return flight arrangements, if you are flying home on Saturday after the workshop, try not to book a flight too early. From our location allow 1½ hours to get to the Florence airport or 3 ½ hours to get to the Rome airport.

For suggestions about getting to Rome or Florence, accommodations or other logistics, please consult our Traveling to Italy link in the main menu bar above. Renting a car from all the major rental agencies is possible if you prefer to be more independent during the week.

If you have time, it is a nice treat to stay in Florence before the workshop starts.  It gives you a chance to get over jet-lag while at the same time allows you to see this incredible Renaissance City.  It is filled with incomparable artwork, architecture and history – not to mention great shopping.  Why not stop in for a few days.  (Look at our Travel to Italy tab above for accommodations suggestions.)


Florence: Sunrise Over City, photo by Anne Benvenuto


The side of the Duomo, photo by Andy Holtzman

Linda at SF-ESThe Food: For us at Il Chiostro, helping our guests experience the food in one of the earth`s richest, most sensual areas is our pleasure. This area is part of Italy`s famous wine and olive oil producing region, but is specifically famous for truffles. Here we want to expose you to the wonders of simple Italian cooking. Linda, a director and founder of Il Chiostro, will be your personal chef.  She uses seasonal, organic products, locally produced by small farms and family shops.  She creates her own twist on pasta dishes, shops in local markets for fresh mozarella and peccorino for our dinner tables. Tuscan cuisine is a simple art that has been refined over the centuries to surprise our palates while the wine comforts our souls. Come explore what food can really be all about.

Terrace Lunch2-AH 2013 Terrace Lunch-AH 2013

An excerpt from a recent article in the NY Times (February, 2013):

The diet that seems so valuable is our old friend the “Mediterranean” diet. It’s as straightforward as it is un-American: low in red meat, low in sugar and hyperprocessed carbs, low in junk. High in just about everything else — healthful fat (especially olive oil), vegetables, fruits, legumes and what the people who designed the diet determined to be beneficial, or at least less-harmful, animal products; in this case eggs and low-fat dairy. This is real food, delicious food, mostly easy-to-make food. You can eat this way without guilt and be happy and healthy.

Linda-Michael with glasses-smallAbout Your Il Chiostro Hosts:  Linda and  Michael, Il Chiostro’s directors, will be hosting you at San Giovanni d`Asso.  Linda will be our chef while Michael will coordinate our excursions.  They have been organizing workshops in Italy since 1995. You can read more about them by following the About Il Chiostro link. For this week the owners of the palazzo will turn their home over to us so we can live like a noble Italian family ourselves.

In addition to your workshop, optional activities offered with this program will focus on the cultural, gastronomic, historical and artistic heritage of Tuscany. This area has been an inspiration to countless people for centuries. What Tuscany offers its visitors is truly astounding:

Art – San Giovanni d`Asso is located near the cities of Medieval Siena and Renaissance Florence packed with some of the most famous masterpieces in the world.

Wine -You are in the heart of the wine growing region, synonomous with the most famous wine that Italy produces – Chianti. But the innovative Tuscan vintners are also producing Super Tuscans, red varietals that are quickly ascending the ranks of world-class wine.

History – this area was settled by the Etruscans centuries before the Romans were a civilized society. Their necropoli dot the fields throughout the area. Nearby towns like Radda, Vagliagli and Castellina date from the early Middle Ages. Florence was the birthplace of the Italian Renaissance. San Fedele witnessed most of this from its panoramic perch atop the hillside.

Foodcucina povera is the typical Tuscan cuisine that has become popular around the world. The recipes are simple, emphasizing local and seasonal products: porcini mushrooms, salumi, legumes, vegetables, pasta, bread and game meats. Visiting an outdoor food market, you will understand the wisdom of this very healthy cuisine.

Crafts – perhaps the harmony of the landscape has been the inspiration for many local craftsmen. Exquisite hand-painted ceramics are the prime example, closely followed by mosaics, leather, woodworking, and textiles.


Montalcino by Michael Ferris