Autumn Arts Festival – Free Yourself: A Sketching and Painting Retreat with Karen Hewitt Hagan
Karen Hewitt Hagan
October 19 - October 27
$4475The Autumn Arts Festival is our grand finale of the year, and this workshop is just one of four inspiring options. If your friends or family join, each of you can choose your own workshop and then come together for shared meals and activities. To learn more about the festival, click here or scroll down to “More on the Autumn Arts Festival” below.
Program Description: Join Karen Hewitt Hagan for an inspiring 8-day Sketching & Painting Retreat at the beautiful Dievole Wine Resort, nestled in the heart of Tuscany. Surrounded by panoramic views and the charm of a 900-year-old winery, you’ll be immersed in the perfect setting to create art from the heart.
You’re welcome to work in any medium you prefer, such as ink, oil, acrylic, pastel, or gouache. However, bringing a sketchpad, a Sharpie, and a small watercolor set is highly recommended, especially for beginners. All levels of experience are very welcome.
The week begins with Karen demonstrating sketching in Sharpie on paper, enhanced with watercolor washes. As the days unfold, she’ll guide you in developing those initial sketches into expressive small paintings on canvas boards. Through daily demos and personalized instruction, you’ll explore how to build compelling compositions, simplify color theory, and infuse your travel sketches and paintings with your own unique voice.
With over 30 years of experience painting en plein air in oil, Karen is also a seasoned studio artist working in both oil and acrylic, as well as an avid travel sketcher. Her work ranges from impressionistic and representational to abstracted styles. Since 2007, she has been leading workshops in Italy with Il Chiostro, sharing her passion for capturing place and spirit through paint.
Join Karen in the Tuscan countryside to learn, explore, and play as you rediscover your creative spark. You’ll be encouraged to sketch, journal, and paint at your own pace. This retreat is designed to help you return home with a sketchbook full of memories, captured in line, color, and words, and new painting skills to bring more joy and freedom to your art.
Our Daily Schedule: Karen will do short sketching or painting demonstrations each morning after breakfast, a two-hour break at lunch, and free time in the afternoons to paint with Karen or explore at your own pace, then an optional opera appreciation before dinner. Dinners will be filled with lively art and inspirational discussion.
If you’re an experienced painter and want to venture out on your own schedule and ask for feedback or a private critique later, this retreat allows you to follow your inspiration in free form. If you’re a newer painter, Karen will be sketching or painting every morning (except when we’re touring) and will be there to guide you step by step on your individual painting journey. Each afternoon will be “free paint” or “free sketch” time. Karen will be doing the same, and if you want instruction in the afternoon, you can paint along with her, or you can be “free”. Get as much or as little instruction as you choose and rewrite your art story here in beautiful Tuscany. Specific supply lists for your choice of medium to be provided.
If you’re a newer painter and can arrange to meet Karen at her home studio in Charleston, SC, or Pompano, FL, one introductory 2-hour class is included for no charge.
There will be three concurrent creative workshops taking place at the resort during your stay. Karen’s Free Yourself: A Sketching and Painting Retreat coincides with the Autumn Arts Festival at Dievole, when Il Chiostro Workshops take over the entire resort. Paint or sketch as much, or as little, as you like, follow your inspiration, and connect with fellow painters, photographers, and chefs.
Midweek features a special “Scramble Day,” when participants are invited to visit one of the other workshops to sample what they’re exploring. Each evening, you can also enjoy an optional Italian Opera Appreciation presentation before dinner.
Price: $4,475 p/p; optional supplement:
- Single room $795 (limited number available)
Includes:
- Room (double or single with supplement) with full bathroom-8 nights
- 2 meals per day (dinner with wine and a full Tuscan breakfast)
- Workshop tuition and fees (except where noted)
- General activities (except where noted)
- Transfers between the Siena train or bus station and Dievole
Departure is on the morning of October 27th.
General Activities: Open to All Participants (in addition to workshop):
Most activities take place in and around the 900-year-old Dievole estate & vineyard.
- Winery tour and tasting, featuring Dievole`s Chianti Classico
- Italian Opera Appreciation classes every evening before dinner
- Excursion to Siena
- Special dinner in the wine cellar
- Various topical excursions with your class
- Pig Roast celebrating the harvest and the arts
Price does not include:
- Airfare
- Museum admissions
- Independent lunches
- Art supplies, laptops, or other equipment for workshops.
- Gratuities – always appreciated by our talented Dievole staff
To Register: Just click on the Sign Up Now button. A non-refundable deposit of $800 is required to secure your spot in the workshop. Payment can be made online with a credit card or PayPal. 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 before the workshop with information about Italy, a supplies list, and an electronic invoice for the balance. Final Balance is due by August 15th. Any time before 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.
Cancellation policy:
$800 deposit is non-refundable. For cancellation:
- 60 days prior to workshop, full refund due less non-refundable deposit.
- 30-60 days prior to workshop, 50% refund of balance paid allowed, less non-refundable deposit.
Less than 30 days before the workshop, no refund due.
Il Chiostro recommends personal travel insurance to cover the possibility of unexpected or last-minute cancellation.
Contact us for more information: info@ilchiostro.com or speak to us live at 800-990-3506.
More on the Autumn Arts Festival: At the end of October, Il Chiostro celebrates the harvest time of the year in Tuscany, hence our Autumn Arts Festival. We offer 4 separate workshops that will happen concurrently throughout this 8-day celebration of the arts, the harvest, the wine, and this wonderful region of Italy. While you are participating in your workshop, friends or partners might enjoy participating in one of the other three programs:
- Tuscan Cuisine with Michael Vignapiano
- From Landscape to Figure: A Renaissance Journey with Lynn Travis Stender
- Photography with Local Photographer Alfredo Falvo
In addition to your selected workshop, everyone can enjoy Italian Opera Appreciation lectures with Prof. Patricia Pease each evening before dinner. These free and optional lectures are open to all registered participants and are an excellent opportunity to enjoy another activity that will broaden your musical horizons.
Dievole Chianti Classico Winery, Tuscany
Participants in the Autumn Arts Festival will stay in Dievole's 16th-century inn and guest houses floating in the magnificent Tuscan hills. We take over the whole winery, so it will begin to feel like home after a few days. The entire facility recently underwent a major facelift, transforming all rooms into spacious, luxury lodgings. Rooms are doubles or suites with modern bathrooms and heating.
A limited number of single rooms and suites are available for a supplement.
Dievole will seem more like a family inn rather than an impersonal chain hotel. Dievole is located in the town of Vagliagli, about 12km northeast of Siena and 40km south of Florence. If you wish to explore the area independently during your stay, we recommend renting a car. The link below will give you a glimpse of the winery:
Click here to visit Dievole's website...
Visit them on Facebook: facebook.com/dievole
We will pick you up in Siena anytime between 1 and 5 pm on the first day of the program. The recommended arrival airports are Florence or Rome, from where you can take a bus or train to Siena. Florence is closer, but there are no direct flights from the US. You would have to change in another European city. Rome provides more flight options.
The bus/train from Rome to Siena is about 3 hours.
We can also arrange for a car to pick you up from Florence or Rome. You pay the driver directly. Just let us know a few days in advance so we can make the arrangements for you.
If you are departing from Rome on the last day, remember it is 3 hours by car or bus from Siena, so try to book an afternoon flight.
If you have time, you might consider lingering in Italy for a few extra days on either end of the festival. Allow the Italian rhythms to seduce you. A few days in Rome or Florence upon arrival is a wonderful way to get over jet lag. For other travel help, check our Travel to Italy web page.
Specific Travel information to get to Dievole:
By Train: There are regularly scheduled trains from all major towns and cities in Italy. Head towards Siena. From Rome, there are several trains daily from the main station (Termini). You don`t need a reservation. Although you purchase a through ticket, it is necessary to change trains at Chiusi. The ride takes about 3.5 hours (approximately 240 km) and the cost is around $20.
NOTE: In Italy, it is the law to stamp your train ticket in the little yellow meter near each train platform. Failure to do so can result in heavy fines, even if you plead ignorance.
By Bus: There are also buses from almost anywhere in Italy to Siena. These are modern and comfortable coaches.
From Florence: buses leave the SITA terminal (next door to the train station) nearly every hour. If you take Siena Rapida, the ride is direct on the highway and should take 1 hour.
From Rome: the ride takes 3 hours (non-stop). If you plan to arrive at the Rome airport and plan to come directly to Siena, this is the quickest method. From the airport, take the train on the left-hand track to the Tiburtina station (NOT Termini). From there, go outside into the parking lot. If you are already in Rome, you can take the Metro to the Tiburtina station. Take the B (blue) line towards Rebibbia. Follow signs to Pzle. Stazione Tiburtina.
With the long side of the station at your back, cross under the overpass into the parking lot. Buy your ticket from the building marked Biglietteria C (17.50 Euros, approx. $20); the bus usually leaves from Gate 8. These buses leave every day at regular intervals. To get current fares and schedules for the Flix bus, you can check their website: www.sena.it.
Once in Siena, get off at the Siena train station (Ferrovia). Don’t get off in the center of Siena.
Travel Agents & Insurance: Over the last few years, the way we travel has undergone significant changes. For that reason, we now encourage everyone to use a professional travel agent when arranging their trips. Travel agents save you time and stress by handling all the details and tailoring your itinerary to your needs. One of the most important services they offer today is helping you choose and enroll in the right travel insurance program. With the continued possibility of schedule changes or postponements, travel insurance has become essential, and selecting the right plan on your own can be overwhelming.
If you encounter any issues during your travels, your agent can provide quick support and solutions, taking the pressure off your shoulders. While booking through online sites like Expedia or Hotels.com may seem more convenient or less expensive, they offer little help if you need to modify your plans. A travel professional, on the other hand, is there to assist you every step of the way, ensuring a smooth and worry-free travel experience.
If you choose to Go It Alone, we highly recommend taking out travel insurance for the trip in the event of any unforeseen obstacles to your travel. We recommend Travelex (800) 504-7883 or Travel Guard International (877) 901-7599.
Tuscany in autumn is a landscape reborn. The hills turn russet and gold, the air grows clear and bright, and the light, that unmistakable Tuscan light, softens into something painters chase and poets never quite capture. Olive trees shimmer in silver-green rows, and the woods deepen with mushrooms and chestnuts. Across the valleys, the scent of the grape harvest lingers, a quiet reminder of the season’s purpose.
This is the time when the land belongs again to the locals. The hilltowns, free from summer’s bustle, settle into a slower rhythm. In workshops and kitchens, hands turn the harvest into tradition, olive oil pressed fresh, prosciutto cured, and Chianti aged to perfection. Every festival, from the vendemmia to the celebration of the wild boar, becomes a study in community and craft.
For artists, autumn here is a masterclass in color and light. The skies are clear, the shadows long, and every turn of the road offers a composition waiting to be sketched, painted, or written. Inspiration feels almost tangible, carried on the crisp wind, reflected in every terracotta wall and cypress-lined ridge.
And at the heart of it all lies Siena, proud, medieval, and timeless. Her museums and churches breathe quietly now, her piazzas echo with the sound of footsteps instead of crowds. Every stone seems to hold a story, every view a palette. In autumn, Siena invites artists not just to look, but to see.
I'm after the light, it's what makes an ordinary scene spectacular!
Whether painting on location outside or inside with a model, Karen Hewitt Hagan’s paintings depict a strong feeling of light and include rich, dramatic brushstrokes.
Theresa Golas, Director of the Iredell Museums, said: “She has an innate sense of color and composition, and when it is coupled with the way she handles the media, magic occurs.”
Residing in Charleston, SC, Karen exhibits at Hagan Fine Art Gallery in Charleston, The Gallery at Sweetgrass at Isle of Palms, SC, and st City Art Gallery, Greenville, NC. She is a frequent juror for The Plein Air Magazine Art Salons and has studied and trained with many contemporary masters.
She credits working outdoors, en plein air, as one of the most important parts of that training. “Nature is truly the best teacher”. Hagan was presented with the Award of Excellence at the COPA Plein Air Painting Event in Charleston, SC, and was a signature member of The Plein Air Painters of the Southeast.
Her book, Karen Hewitt Hagan: An American Impressionist (published by Morton Arts Media), has a section dedicated to the Contessa's Farm in Italy, where she taught for Il Chiostro many years ago.
Website: Karenhewitthagan.com
