“If you can’t live longer, live deeper.”
— Italian proverb
PLEIN AIR TUSCANY
Painting Journeys into the Heart of Tuscany
PASSION FOR
PAINTING, FOOD & PLACE
CORTONA, TUSCANY
Join us in August 2025 & April 2026
PAINTING, HIKING & DISCOVERY IN CORTONA
Imagine spending a week immersed in the quiet magic of Cortona—wandering its hidden backroads, hiking its rolling hills, and capturing its beauty on canvas. This is more than a retreat; it’s a journey of artistic growth, cultural immersion, and deep inspiration.
Set in the sublime landscape of the Val di Chiana, the region offers breathtaking scenery at every turn. Your days will be filled with artistic progression, guided hikes, and guided exploration of one of Tuscany’s most historic hill towns. Each evening brings inventive, locally-inspired meals, generous pours of wine, and a sense of camaraderie around the table.
Since 1986, Garrett has ventured deep into the heart of Tuscany—down remote roads, through quiet valleys, and into the soul of small towns. His passion for all things Tuscan is contagious. By the end of the week, you’ll not only have a deeper connection to your art, but you’ll also be tossing around a few charming Italian phrases of your own.
OUR DAYS
The workshop includes eight days of dedicated instruction, with one to two painting sessions each day. Whether you're a seasoned painter or just beginning your creative journey, the program is designed to support your growth. With a maximum of 13 participants, the group size is intentionally intimate, creating a warm and focused environment where every artist can flourish.
The experience is led by Garrett Speirs, an accomplished painter and teacher with over 34 years of experience capturing the essence of Tuscany. Garrett first arrived in the region as a student in 1986 and instantly became an observer of “everything” Italian. Since then, he has returned every year to paint, explore, and deepen his connection to the Tuscan way of life.
Montepulciano
Join us for an immersive plein air painting set against the stunning backdrop of the Tuscan hills. Each day, we’ll explore essential painting concepts, from practical techniques to the intricacies of optical color. Experience hands-on demonstrations on painting clouds, incorporating architecture into your landscapes, and mastering color mixing. Please note that our painting locations will vary based on weather and other conditions, and participants should be prepared for walks ranging from half a mile to four miles, including steep paths. Good physical fitness is essential for adventure!
Gouache Painting
Join us for engaging demonstrations in gouache and watercolor, perfect for artists on the go. These mediums are lightweight and travel-friendly, eliminating the need for bulky oils and canvases. Plus, with no toxic fumes to worry about and instant drying times, you can focus on your creativity. We’ll be working in sketchbooks on watercolor boards, making it easy to capture your artistic visions anywhere.
Garrett's Sketchbook
SANCTUARY
Welcome to Your Digs in Cortona!
Get ready to settle into one of Cortona’s charming boutique albergos, where comfort meets character in the heart of this historic hill town. Each room—varying in size, views, and unique personality—offers a cozy atmosphere designed for a delightful stay.
Guests will enjoy complimentary breakfast and the ease of being steps away from Cortona’s rich culture, cuisine, and stunning views.
Participants can choose between two levels of accommodations:
• A lovely, locally run albergo with Tuscan charm
• Or a higher-end albergo for a bit more luxury and style
Our View
Mangia
PRIMA COLAZIONE-breakfast at your BnB
Your day will start with a bounty of fresh baked goods, fresh local fruits, jams, honey, fresh yogurts and eggs. But most importantly you'll enjoy a perfect cappuccino.
PRANZO-lunch
Most days we will take our lunch in the field. We will carry our lunch with us. Mostly this will be wonderful handmade sandwiches from a local market.
CENA-dinner
Join us for an enchanting culinary journey through Cortona! Each evening, Garrett has selected a variety of delightful Trattorias and Osterias for us to explore. Indulge in exquisite meals paired with local wines, all included in your program. After savoring these delicious courses, retire your cozy accommodations, recharged for another day of painting and adventure ahead.
Evenings begin with aperitivo at a local cafe
A WORRY FREE WEEK
Spring 2026!
SO WHAT'S INCLUDED?
August 27nd-September 3rd, 2025!
Summer 2025: Please note group size is extremely limited. Only 5 participants!
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Join us for an intensive, immersive week of plein air painting in the heart of Tuscany.
Using gouache as our expressive medium, we’ll explore the luminous light, atmospheric vistas, and ancient textures of Cortona — a hilltop town rich with Etruscan history, Renaissance architecture, and timeless Italian charm. Over six focused days, we’ll absorb the rhythms of this historic place through paint. Mornings will be spent in the field — studying light, sketching architecture, capturing fleeting scenes. Afternoons will offer guided lessons in gouache technique, composition, color mixing, and critiques to push your work further. Whether you're refining your plein air skills or diving into gouache for the first time, this week is designed to deepen both your practice and your vision. -
Accommodations for 6 nights. Choose between a authentic and simple Tuscan albergo or a small boutique hotel with a more refined atmosphere.
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6 days of gentle guided instruction from Garrett Speirs. Each day features one or two sessions drawing or painting at carefully selected locations, allowing you to fully absorb the surrounding beauty. Participate in daily critiques and discussions centered on plein air painting, all while honing your skills in a nurturing atmosphere. Discover both curated and hidden gems as you explore the expansive hills, uncovering the artistic inspiration that Cortona provides.
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All dinners are provided. Lunches are included when we are out painting. Wine & beverages are included with dinner! Wines are typical regional red and white varietals. *Beverages while hiking are up to your personal preferences.
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Daily guided excursions to abbeys, historic sites, famous paintings. Historical discussions are included for those who are interested in art history. This includes entrance to all museums and churches.
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Train and bus tickets to sites, in the event of rain we will have plenty to do! Spring 2026: Space is limited to 12 students. Accommodations for 8 nights. Choose between a authentic and simple Tuscan albergo or a small boutique hotel with a more refined atmosphere: a fully-staffed, historic boutique hotel. Comfortable, stylish rooms all with private bathroom. The hospitality is next-level.
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8 days of gentle guided instruction from Garrett Speirs. Each day features one or two sessions drawing or painting at carefully selected locations, allowing you to fully absorb the surrounding beauty. Participate in daily critiques and discussions centered on plein air painting, all while honing your skills in a nurturing atmosphere. Discover both curated and hidden gems as you explore the expansive hills, uncovering the artistic inspiration that Cortona provides.
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All dinners are provided. Lunches are included when we are out painting. On our excursion to Arezzo students will be free to take lunch at any number of wonderful trattorias. Wine & beverages are included with dinner! Wines are typical regional red and white varietals. *Beverages while hiking are up to your personal preferences.
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Daily guided excursions to abbeys, historic sites, famous paintings. Historical discussions are included for those who are interested in art history. This includes entrance to all museums and churches.
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Train and bus tickets to sites.
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A very special evening hosted by a regional wine maker in Cortona. Dinner includes wine tasting at a local trattoria.
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Memorable afternoon wine tasting with Marco Molesini of Molesini Wines.
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A captivating day trip to Arezzo, where you'll explore Piero della Francesca's renowned fresco, "The Legend the True Cross." As one of the most influential figures the Renaissance, his work continues to inspire contemporary artists today. After immersing yourself in art and history, enjoy some time to shop and discover the charming streets of this lesser-visited town.
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Advise with travel plans and what best to bring, a pre-trip welcome folder with art terms, formulas for painters, and Italian essentials for visitors to Italy.
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A pre trip "orientation" at my studio in Santa Ynez, for those who can attend.
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Individual pre-trip drawing lessons and instructions done remotely with each student. Post trip critiques available for students upon return.
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Students wanting other experiences such as cooking classes, winery excursions, visits to Florence, Montepulciano, or other towns can inquire about options we offer! Just ask.
AND WHAT'S NOT INCLUDED?
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Airfare to Italy
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Transportation from airport to Cortona. This can be arranged with a private driver.
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Travel Insurance!
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Personal expenses (think gelatos).
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Return transportation to airport, drivers available. Please inquire.
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Lunches if it is a rain day.
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Pre dinner aperativos.
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Beverages while we are out in the countryside.
WHAT ELSE SHOULD I KNOW?
We will be doing daily walks which can be short or up to 4 miles. We will be walking on pathways and through olive orchards. Please ensure you are in good physical health, as some routes include steep hills (all of Cortona!). Get ready for an unforgettable experience in nature!
