Join me for the next chapter in the Sky&Clouds&Land&Air Workshop Series.
For the first time, Sky & Clouds & Land & Air is coming to Tuscany, with a week-long workshop in the heart of the Chianti region surrounded by rolling vineyards, wooded hills, and expansive views across the Tuscan landscape at the amazing Borgo Casa al Vento.
ON LOCATION: TUSCANY
THE LOCATION
Sienna and the Chianti Region
Our artistic journey begins at Hotel Italia Siena, a welcoming retreat where classic Italian charm meets modern comfort. Ideally located just outside Siena’s historic city walls, this family-run hotel offers the perfect home base for our group as we explore the beauty, history, and creative spirit of this charming city.
Guests will enjoy comfortable accommodations, warm hospitality, and a delicious breakfast each morning before setting out for a day of artistic discovery. From the hotel, Siena’s medieval streets, Gothic architecture, and vibrant piazzas are just a short walk away, providing endless inspiration for sketching, painting, photography, and soaking in the atmosphere of one of Italy’s most captivating cities.
After a day of exploration and creative pursuits, Hotel Italia Siena offers a relaxing place to gather, reflect on the day’s experiences, and prepare for the adventures ahead. Its convenient location and welcoming atmosphere make it an ideal setting for the start of our Tuscan art experience.
From there, we will journey to Borgo Casa al Vento for the primary portion of our program. Borgo Casa al Vento is just that - a borgo or small hamlet. Dating from the medieval era, this village has been renovated to have a second life as an authentic winery-hotel in the middle of the Chianti hills of Tuscany. All rooms are different, created from the homes of the borgo. All have modern bathrooms and conveniences like Wi-fi, refrigerators, and air conditioning.
Located in the Tuscan countryside just outside Gaiole in Chianti, Borgo Casa Al Vento is a restored medieval village that beautifully captures the essence of Chianti.
The property is surrounded by vineyards, providing a serene and picturesque backdrop for a week of painting. The farmhouse retains its Tuscan charm while providing comfortable accommodations with modern amenities, like air conditioning and Wi-Fi. The on-site restaurant, where the group will dine together, serves farm-to-table dishes that showcase local cuisine, prepared with seasonal and traditional ingredients, and wines produced in the surrounding vineyards.
The farmhouse offers a wellness center with unique treatments like wine baths, wine therapy, and various massages for anyone who wants to enjoy the spa during free time. The property also features a panoramic pool, a small lake, and sports facilities, including a tennis court and table tennis, all available during your stay.
Casa al Vento is also well positioned for exploring some of Tuscany’s historic towns and cities. Siena is approximately 30 minutes away, while Florence is about an hour by car. Closer to home are the hill towns of Radda in Chianti, Castellina in Chianti, and Greve in Chianti, as well as the medieval village of San Gimignano. The area offers a rich mix of history, architecture, and landscape, making it possible to experience the region beyond the places where we’ll be painting.
THE WORKSHOP
From observation to plein air sketch to studiowork.
Developed over years of teaching both in-person and online with students from around the world, this course has become one of my favorite methods for balancing technical growth with intuitive painting. In this special on-location edition, we add the direct experience of plein air painting to the course’s core structure, working each day in the Tuscan countryside, an environment of shifting light, layered distance, and rich atmospheric variation.
Students will begin this workshop by painting small-scale plein air sketches directly from observation using a limited palette. This exercise helps students develop a working knowledge of both seeing and simplifying the painting process.
We’ll demo and discuss composition, drawing, value studies, color notes, and quick studies as we work our way to fully developed paintings. Through this cumulative practice, participants build fluency with materials, sharpen decision-making, and develop a stronger understanding of how observation becomes painting. Just as importantly, they begin to cultivate a more personal and confident relationship to their own process.
This course is open to all skill levels. The atmosphere is relaxed and welcoming while remaining deeply instructional, so whether you are new to painting outdoors or an experienced artist looking to further develop your plein air approach, there is a place for you in the workshop. Demonstrations, one-on-one guidance, group discussions, and daily working sessions provide a clear structure without sacrificing the freedom to explore at your own pace.
Students will leave with practical plein air experience, a stronger command of color, value, composition, and simplification, as well as strategies for translating outdoor studies into resolved studio paintings. More than anything, the Sky, Clouds, Land, & Air workshop is a vehicle for building confidence in painting, expanding visual language, and moving closer to your singular creative voice.
When I first began plein air painting, I struggled with how different the process felt from my studio practice. Before I could make work that felt successful, I had to redefine the fundamentals into a methodology that fit the way I learn and work.
This meant embracing the role of a beginner repeatedly—returning to core principles and practicing them until they became a fluent visual language. That methodology evolved into the what I refer to as the sketching mindset.
So much of the Sky&Clouds&Land&Air experience is rooted in the idea of practicing practice, and the plein air component is no different. We paint on location with an exploratory spirit—seeking what feels beautiful, challenging, or personally relevant to our ongoing questions in painting. We work directly with nature, experiencing time and place while recording our perceptions.
This can take many forms: drawing, value studies, color notes, multi-day paintings at a single site, or a series of quick studies. Over time, this cumulative practice—combined with direct observation—builds skill, fluency with materials, and a rich catalog of sketches to inform studio work. More importantly, it fosters a deeper relationship with your creative self, creating space for growth that extends beyond the subject matter itself.
In this workshop, clouds, sky, land, and air are the vehicle—not just for creative proficiency, but for cultivating confidence and comfort in the search for your singular artistic voice.
THE SCLA EXPERIENCE
Balancing skill building with intuitive painting practices
What You’ll Gain
Plein Air Experience
Instruction in the sketching mindset: decisiveness, clarity, adaptability
Understanding how to respond to changing light, atmosphere, and weather in real time
Development of quick decision-making skills under time constraints
Mastery of simplification strategies for complex natural scenes
Increased technical proficiency in handling paint, color mixing, and composition
Techniques for color temperature and value relationships in outdoor conditions
Familiarity with efficient plein air setup and portable materials management
What You’ll Gain
Studio Translation
Strategies for transforming plein air studies into resolved paintings
Techniques for preserving freshness while working in the studio
Expanded composition and design skills using fieldwork as reference
Methods for scaling up plein air sketches into larger, more developed works
Understanding how memory, time, and interpretation shape studio painting
Instruction in the studio mindset: refinement, patience, intention
A process for returning to foundational principles as a tool for growth
A deeper connection to your creative self, fostering personal voice and long-term practice
MEALS & ADDITIONAL ACTIVITIES
Meals: Your stay combines two unforgettable Tuscan settings: Hotel Italia Siena and Casa al Vento.
At Hotel Italia Siena, you’ll enjoy a comfortable, family-run hotel just outside Siena’s historic city walls. Rooms are stylish and well-appointed, offering a calm and convenient base with easy access to the city. Each morning begins with a generous buffet breakfast featuring fresh pastries, fruit, and regional specialties, perfect for a relaxed start to the day.
Beautiful Casa al Vento was an actual village in the medieval days. Now it is a winery in the middle of the Chianti landscape in Tuscany, situated between Siena and Florence. This authentic venue will be your home away from home.
Dinners are prepared in the on-site restaurant using local, seasonal ingredients, making every meal a feast! We’ll eat together in the dining room each evening, enjoying the cuisine and the wine from the hills right outside our windows. Breakfast is served buffet-style. You are free to eat indoors or out on the terrace. There is a lovely private pool at the end of the garden, which makes for the perfect end to a long day of painting.
Additional Activities: Our daily painting will be combined with other adventures, such as:
2 days/nights exploring Siena
Excursion to Radda
Winery tour and tasting
Optional cooking class
Variety of plein air locations to paint landscapes, villages, and the Tuscan light
After excursions or painting on location, we’ll return each evening to our borgo, imagining what life here was like 500 years ago. We can enjoy the surroundings, have a glass of wine, and relax after the day’s rich experiences. Then we will move to the dining room for our local chef’s authentic, homemade Tuscan meal, recapping the day’s adventure with good company.
REGISTRATION
COST:
$4,450 p/p; non-painters $4,150
Optional Supplements:
$695 for a single room, limited availability
Includes:
Shared double room in Siena and Casa al Vento (single available for a supplement, see above)
Daily traditional breakfast and dinner, including wine
Daily painting classes and individual guidance
½ day painting excursion to Radda
Pick up from Florence train station at 3:30 pm upon arrival on Saturday
Transfer to Florence station or the airport on the final day
Fully escorted by Il Chiostro program managers for all outings and excursions
Does Not Include:
Airfare
Lunch (lite lunch will be available for purchase in the restaurant on days we are not out on excursion)
Art supplies
Independent meals and sightseeing
Gratuities – much appreciated by your hard-working staff. We suggest €10-20 per participant per day.
Cancellation policy:
$800 deposit is non-refundable. For cancellation:
60 days before the workshop, full refund due less non-refundable deposit.
30-60 days before the 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.
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 a direct deposit from your checking account. 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.
The final balance is due by March 31st, 2027. 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.
IMPORTANT NOTE**
This workshop is organized in partnership with the amazing team at Il Chiostro.
For 30 years they’ve designed unique educational and cultural slow travel experiences for creatives seeking meticulously crafted immersive journeys.
To sign up for this workshop, please click the photo below or the ‘REGISTER’ button which will take you to the Il Chiostro website.
Follow their prompts or call 800-990-3506
MATERIALS
