Capture the Natural Beauty of Tuscany En Plein Air

DATES: 06/19/2021 - 06/26/2021
LOCATION: Tuscany, San Fedele
PRICE: $3,095.00

Sudbury River, Concord, MA, 48X24, oil on canvas by Jill Pottle

Jill M. Pottle is a fine artist from Massachusetts who exhibits her paintings and pastels locally and nationally.  She has her MFA from the Museum School in Boston, and studied with the group titled “The Boston School”, as interpreted by the late American painter R. H. Ives Gammell. Jill is an accomplished instructor and artist who has been teaching for over 30 years. Her works have been included in shows at the Three Stones Gallery, W. Concord, and the East End Gallery in Provincetown, MA.  Jill has had a show at the St. Botolph’s Club in Boston, and was the artist in residency at the Fruitlands Museum in Harvard, MA.  She has been included in a variety of collections such as MGH, Hebrew Rehab. Center in Roslindale, MA and Sterling Drug Inc., Fidelity in Boston. She was invited to and attended “Art Week” on Great Spruce Head Island in Maine, the summer home of her mentor Fairfield Porter.

Jill Pottle is wonderful to paint outdoors with on site with.  She makes the entire session enjoyable and lessons easy to absorb. Starting with packing up supplies and getting to the site, to choosing the scope of what you’ll paint, she guides you through it all.  Jill helps the students decide what is important for a good composition, then guides each one on choosing which shapes and colors to help them paint what is seen.  She teaches how to make a pleasing image from start to finish.  Jill is a very talented painter and is also very able to teach in a challenging and fun way.   –Dana Reinhard

I’ve enjoyed many painting trip classes with Jill.  She’s a wonderful painter and I always learn a lot from her, especially from her excellent demonstrations on site.  She’s also very organized so you’ll make the best use of your precious painting time.  If you go with her to Tuscany you’ll not only get to paint in a wonderful place but your painting skills will make a leap forward. I highly recommend her.   -Linda Christine-Herot

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Jill Pottle’s oil and acrylic painting classes, particularly the en plein air ones, are full of creative exuberance and fun explorations of color, composition, and personalized paint application. Last summer my adult daughter and I shared one of her Maine workshops together and it was one of the best “working” vacations ever! What one has to like about Jill’s instruction is she is able to instruct productively and not stifle individual style or sensibilities for subject matter, allowing each individual to become their own “better” and eventually “best” possible painter. She makes the search joyful and evocative, yet shares positive criticism, and always generates an interesting class collaboration. Tuscany bound sounds great.  -Patricia Loheed


Have a life-transforming visual experience painting with instructor Jill Pottle!
Learn color & light en plein air in the Tuscan countryside
through oils, acrylics or gouache while enjoying fabulous wine, Italian cuisine, and great company!

Eden Vermont, 14X11, oil by Jill Pottle

Imagine yourself waking up with a view of the vineyards in San Fedele. After breakfast, get ready for your morning painting lesson, en plein air. After a creative morning, working on your landscape painting, break for lunch and perhaps a little wine. In the afternoon, visit a hilltop town for a walk about or cappuccino and people watching.  As evening arrives, enjoy a gourmet dinner of Italian cuisine.

Late spring is a beautiful time of year to paint the hills and valleys, olive groves and ancient structures of the Tuscan landscape.  It’s an extraordinary quilt of vineyards, monasteries, and villas; a place one can feel the history in the rich golden colors of the earth.  This week will focus on building confidence as a painter and advance ones painting skills outdoors with Jill’s expertise.

Great Meadows in Concord, MA 36X18, oil on canvas by Jill Pottle

Jill offers a supportive approach for her students in oils, acrylics, or gouache. Through demonstrations and constructive guidance, Jill will help each attendee to design a dynamic composition, discover the colors and light of this luminescent scenery, and evolve their painting techniques. Most days will be spent painting en plein air style in addition to 24/7 access to a studio space.

Lovely Sand Beach in Stonington, ME, oil on canvas, 11×14

We will be staying at San Fedele, a beautifully restored ex-monastery which dates back to 1203AD. This is located in the Chianti region of Tuscany between the towns of Vagliagli and Radda-in-Chianti, south of Florence.  This space features elegant lodging with beautifully furnished rooms and modern bathrooms, and the 16th century chapel is used as a large gathering space.  The refectory is used as the dining room, doubling as class space, and there is a U-shaped piazza and three studio/class rooms with work areas.  Each evening we will relax in the monastery to enjoy the surroundings, have a glass of wine, and an informal critique of the day’s work.

All levels in painting welcome with some drawing experience required. Sketch-booking is encouraged on this wonderful journey.

Additional Activities: Our daily painting will be combined with other adventures such as:

  • Day trip to Medieval Siena to sketch, take photos, explore and shop
  • Excursions to nearby hilltowns like Radda, Castellina, Monteriggioni, etc.
  • Visit to Chianti winery for a tour and tasting
  • Variety of plein air locations to paint landscapes, villages, and the Tuscan light
  • Discussions of Tuscan cuisine with our chef

Price: $3,095* p/p based on double occupancy; (non-painters $2,795)

* Early Bird Discount of $100 if registered by December 31, 2019

On Porch, Picnic Cove, ME, oil on panel, 12×12

Final balance due in April of 2020.

Optional Supplements:

  • $550 for single room
  • $250 p/p for a suite (min. 2 persons) sorry, none left


  • Shared double room in restored monastery
  • Daily traditional breakfast and dinner, including wine
  • Daily painting classes and critiques
  • Excursion to Siena
  • ½ day painting excursions to nearby plein air settings and hilltowns (Monteriggioni, Radda, Volpaia…)
  • Pick up from Florence train station at 3:30pm on arrival Saturday
  • Transfer to bus/train station in Siena (not Florence) on final day

Does Not Include:

  • Airfare
  • Lunch (usually available on excursions)
  • Art supplies
  • Independent meals and sight-seeing
  • Gratuities

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: or speak to us live at 800-990-3506.

Borgo San Fedele

— San Fedele is a restored 12th century monastery floating in the Chianti hills —

©Lester Lefkowitz 7003-001Il Chiostro at San Fedele is the combined skills of Linda and Michael of Il Chiostro joining together with Nicolo and Renata of San Fedele to produce a unique and inspiring environment rooted in the traditional Tuscan values of beauty, great food, an appreciation for nature and the value of community.  The monastery, dating back to the 12th century, was meticulously restored using traditional building methods and all original materials. Today, the monastery remains true to its original spirit, rich architectural detail. The 16 rooms and suites where participants are housed have lovely modern bathrooms, screened windows, air conditioning, period furniture, wi-fi internet service, satellite television and minibar, all designed to perfectly compliment the medieval surroundings.

The original soaring chapel is now used as a large art studio or workshop space. The monks’ refectory, where a lost 16th century fresco was uncovered during renovation, is now the dining room connected to a state-of-the-art kitchen and the old stone cantinas where they stored their wine have been transformed into studio and classroom space.

For information about the history of this monastery, Click here to go to San Fedele’s web site…


Rather than  hotel, San Fedele is classified as a historic residence in Italy.  That means that it is an intimate setting, preserved along strict historical guidelines to preserve the spirit of the setting.  The owners are on site to oversee this unique combination of historic landmark and modern day comfort.

Accommodations are spacious shared double rooms or junior suites. Each room, because it was converted from the original structure of the monastery without altering the building, is unique in shape. Furnishings and decor were selected to coordinate with the historic, subdued feeling of the monastery, but in a comfortable, modern style. All rooms have two beds that can be separated into twins or combined into one large matrimonial. There is a sitting area, refrigerator, DSL wi-fi, television, air-conditioning, heating, modern private bathroom with shower and hair dryers.

lester-lefkowitz-room3 lester-lefkowitz-room2

There are a limited number of single rooms available at a supplement of $550.

2 Jr. Suites for a minimum of 2 people are available for a supplement of $250 per person.

Night shot piazza©Lester Lefkowitz 7003-010© Lester Lefkowitz 7184-022Archway from rose garden and breakfast buffet in the refectory (photos by Lester Lefkowitz)

Terrace-MJossThe back of San Fedele is surrounded by a large al fresco dining terrace with the original terra cotta tile designs reproduced down to the smallest details. The terrace overlooks the same organic vegetable and flower garden tended by the monks for centuries. Beyond are the rolling Chianti vineyards that make this part of Tuscany so breathtaking.

Other common spaces include a large classroom carved into the rock of the ancient wine cellar, an expansive private piazza, a 16 x 7 meter swimming pool and sprawling landscaped grounds on a rolling hillside.

To San Fedele-LMFlorence 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.

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 1 ½ 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 ourTraveling to Italy link. Renting a car from all the major rental agencies is possible if you prefer to be more independent during the week.

Fall vineyards

Fall vineyards


Borgo San Fedele sits conveniently on a country road connecting the charming medieval walled town of Radda and the village of Vagliagli. Other nearby hilltowns include Castellina-in-Chianti, Monteriggioni and Volpaia. It is about 45 minutes from San Gimignano and Volterra. Many of these towns have roots in the earlier Etruscan civilization that permeated this area prior to the Romans.

San Fedele is located about 12 km northeast of Siena and 45 km south of Florence.

The Food

For us at Il Chiostro, helping our guests to experience the traditional food in one of the earth`s richest, most sensual areas is our pleasure. The Chianti region of Tuscany is Italy’s famous wine and olive oil producing region. Here we want to expose you to the wonders of simple Italian cooking known in the area as cucina povera. Our chef is a Tuscan native who uses recipes from her mother and grandmother to bring the tradition of not only Tuscany, but specifically the Chianti region, to the table each evening.  We use seasonal, organic products, locally produced by small farms and family shops. Our chef searches for the best of Tuscany to serve you. Tuscan cuisine is a simple art that has been refined over the centuries to surprise our palates while the red chianti wine comforts our souls. Come explore what food can really be all about.

© Lester Lefkowitz 7184-057Candle Light Dinner2-CharlesAnderson
About Your Il Chiostro Hosts
Linda and Michael, and their program managers will host your program in Tuscany. They have been organizing workshops in Italy since 1995 and each person brings a special talent to the program. You can read more about them by following the About Il Chiostro link. At the Tuscan Renaissance Center, the owners of San Fedele, Nicolo and Renata, live on site. They will be available throughout the program to talk about the history of the monastery, the renovation and this area of Tuscany they call home.

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:

Bell tower-smallArt – San Fedele is located conveniently between 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 Chianti region, synonomous with the most famous wine that Italy produces. 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.