free yourself sketching + painting RETREAT
PLEIN AIR (Italy)
October 19-27, 2026 at Dievole Wine Resort
5 of 12 spaces OPEN
unleash your Inner Artist
Join us in Tuscany where the inspiration flows like wine.
Explore in any medium you prefer. For the beginner or pro.
This sketching + painting retreat at Dievole Wine Resort is designed to help you unlock the keys to making art from YOUR heart. Learn and practice exciting new techniques that can revitalize your sprit and your art while in a beautifully immersive Tuscan setting.
Energize and Transform Your Art
What is the difference between a WORKSHOP and a RETREAT?
This RETREAT is designed to accommodate creative travel for both the beginner or the pro allowing for the flexibility you desire. Most workshops are scheduled as 9-5 paint all day sessions. This is different.
If you’re an experienced painter and want to venture out on your own and ask for feedback or receive a private critique later, this retreat allows you to follow your inspiration in free form. If you’re a newer painter, I will be sketching or painting every morning (except when we’re touring or shopping in hillside towns) 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. I will be doing the same, and if you want instruction in the afternoon, you can paint along with me, or you can be “free”. Get as much or as little instruction as you choose and rewrite your art story here in beautiful Tuscany.
Bring a Friend, a Soulmate, or A Spouse
But, this is a limited class size of 12, so please sign up now to secure your space.
Private rooms are limited.
How to Sign Up
Click here to go to Il Chiostro's Website
Email: info@ilchiostro.com
Call: 800-990-3506
Pricing, Private Room Info, Getting There, Accommodations and all the details are on the Il Chiostro website.
$4475
Click Here to Email Karen
Schedule a Call with Karen
Call Karen 843-754-0494
Photo Credits: Il Chiostro Workshops & Dievole Wine Resort
WORKSHOP reviews
"Everything was just right! In fact, more
than just right. It was the experience of a
lifetime. The food, the wine,
the beauty of Italy...
what's not to love?"
-Debra B. Charleston, SC
"Wonderful!
You made a dream come true for me!"
- Wilda T. Charleston, SC
Dievole Wine Resort
30 Minutes from Siena
75 minutes from Florence
Located in Castelnuovo Berardenga, specifically in the hamlet of Vagliagli, in Tuscany, Italy. The resort is situated within an 800-acre estate in the Chianti Classico region, about 12 km northeast of Siena.
"I visited Dievole for a wine tasting afternoon many years ago. It was more than beautiful and I've painted from those photos for a decade. I have seen their guest rooms online and they look amazing." - Karen
Previous Workshops look like this
we explORE, sketch, paint and immersive ourselves fullly in an authentic Tuscan artistic experience.
Since 2007, I've hosted groups in France, The Bahamas, Charleston and Italy, Aboard my Boat, and across the US. It's always a delicious and enriching experience where life long friendships begin. Come along and you may find your art tribe. It's where I found mine. I love them every day.
Watch our adventures on social media and come with us on on the next painting trip! You'll bring home a sketchbook full of your ideas, new paintings and a life time of your own exciting reference photos,
We welcome beginners as well as pros. We were all beginners at one point and everyone has to start somewhere. Why not start somewhere fabulous?
