Creative Watercolor in the Chianti Hills of Tuscany – SOLD OUT

DATES: 09/21/2024 - 09/28/2024
LOCATION: Tuscany, San Fedele
PRICE: $3,895.00

Elaine Allen has been an artist since she was a child – when she used chalk from a broken wall to draw on the slate sidewalk in front of her home.  Her long career has included illustrating an international children’s magazine and creating work for public and private spaces across the US, including Vanderbilt Children’s Hospital and The Brentwood Library in Tennessee, and Joy Gardens in California. She continues her work in both watercolor and oil for shows in the US.

With her passion for teaching, Elaine has created Bright Mind Arts – an art curriculum for active senior centers, Start in Art – art lessons online, and The Creative Well – membership that’s a weekly dip into the creative pool. She instructs local community programs for adults and runs a summer art program for kids.

She holds membership in the National Watercolor Society, The American Watercolor Society, The Chestnut Group – Plein Air Painters, and Sanctuary Artists.

I love to teach art and have been teaching classes, camps, and workshops for many years. I believe that everyone is creative, and each of us longs to find ways to express our unique form of creativity.  

It’s astounding to see some of the life changes that come about because of creative activity. Studies prove what I see firsthand – that fulfilling the basic human drive to create actually changes the brain. I’ve seen students become more confident, have better communication skills, and have enhanced problem solving skills. Making art is therapeutic, so it’s a calming, centering activity.

 A lot of the folks who show up for my classes are looking at what’s next for their lives. I believe that creative work is one of the best things they can do on that journey of discovery. The experience is what is important, not the end result of the work.  

Elaine Allen

Elaine Allen is the teacher I have been looking to find for years.  I have taken several classes over the years but with Elaine I feel a real sense of accomplishment and growth in my art.  I would usually throw away the pieces I made in classes. But with Elaine’s classes I have finished works I am proud of.  She has a knack for really inspiring her students to create.  I would recommend any class you can take with Elaine. She has impressed me in a variety of mediums.  She has even helped me impress myself!  Thank you, Ms. Allen. Please keep doing what you do.  –Vickie Frazier

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I went with this lovely lady to Venice and the experience was AMAZING! I’m not an artist by any stretch of the imagination, and I have to say, I had SO MUCH FUN just PLAYING with sketching and throwing paint around. It got my “crafting juices” flowing again.   Elaine is a FABULOUS teacher and makes it easy and gentle to bring back a sense of creativity in life. If you’re feeling stuck in your creativity, if you’re feeling like you need a soft getaway to feed your soul, JOIN THIS CLASS!  The combination of Elaine and Il Chiostro will soothe the savage beast that is your mind, into a serene, creative, well fed partner in life.  – Amelia McHenry

Elaine was able to take me from a person sitting before a blank canvas to a woman who saw herself as an artist! I created a beautiful seascape that gives me such a feeling of pride.  Thank you, Elaine for bringing out such talent in me – yes, me!  I still can’t believe it! –Jane Meade

Your inherent creativity is humming and stirring quietly in its deep reserve . . . if you’re alive, you’re a creative person. You and I and everyone you know are descended from tens of thousands of years of makers. Decorators, tinkerers, storytellers, dancers, explorers, fiddlers, drummers, builders, growers, problem-solvers and embellishers – these are our common ancestors.  –From Big Magic by Elizabeth Gilbert

Unfortunately the workshop is full.  Please click on the “Sign Up Now” button below to be added to the waiting list.

“Joy in Creativity” is our theme.

We will collect moments to savor in this gorgeous landscape that has inspired painters since before the Italian Renaissance.  We’ll sit in piazzas of small villages, gaze at the rolling Chianti  Hills, stroll through medieval Siena and maybe even sketch a vineyard while they are harvesting the grapes for pressing.

Our luxurious host retreat venue is a haven of serenity. It is the perfect place to view the soft light of the Tuscan sun – so unique and lovely. You will feel the history in every footstep and experience the “thousand years of prayer” that is held in every stone.

Tuscan light, watercolor by Elaine Allen

Our class time will be fun – and easy, especially for a beginner. You’ll learn how to do quick drawings and add watercolor to capture your impressions of this time-honored landscape.

This will be a comfortable intro to watercolor, where you’ll learn how to use a limited palette to achieve a full range of color. Classes will also include simple drawing lessons so you can confidently sketch, and you’ll see how a few well-placed lines can define and simplify a scene. We’ll also collect ephemera and use brief descriptions in our journals to capture the places, the sounds, the scents, and your feelings.  You’ll fill your journal with your experiences and return home with a beautiful, personally painted record of your time in the Tuscan Hills.

We’ll be sure to combine artmaking with a great-big-heaping-serving of PLAY! Class will be in the mornings, and then we’ll have plenty of time to do just that.

Tuscan vineyard at sunrise

A huge advantage to our time here is that it is wrapped in the delightful inclusive experience that Il Chiostro provides. You’ll be sharing your time with other artists in a small group setting. Throughout our week, Il Chiostro will be taking care of us, arranging for the ideal painting opportunities and steering us through this incredible physical and cultural landscape.

Don’t miss this amazing adventure and opportunity for restful, educational, meaningful travel!

Meals and our “Home”

Beautiful San Fedele, a thousand-year-old monastery near Siena, resurrected from ruins and transformed into a distinctive retreat center, will be your home away from home for a full week.

Dinners are prepared by our personal chef using local and seasonal ingredients to make every meal a feast!  We’ll eat together in the dining room of the ex-monastery each evening.  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 painting.

The Duomo in Siena

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
  • Sunday dinner at local winery
  • Variety of plein air locations to paint landscapes, villages, and the Tuscan light
  • Discussions of Tuscan cuisine with our chef

After excursions or painting on location, we’ll return each evening to relax in our 1,000 year old monastery to enjoy the surroundings, have a glass of wine, and relax after the day’s rich experiences. Then we will move to the dining room (the authentic refectory where the monks used to assemble) to enjoy our local chef’s authentic, homemade Tuscan meal, recapping the day’s adventure with good company.

Sketching a Castellina courtyard

Price: $3,895* p/p; non-painters $3,595

Supplement:  $575 for single room, limited availability

$500 deposit due upon registration.  Balance due by August 15.

*Early Bird Discount of $200 if registered by February 1, 2024
Enter ELAINE as discount code


  • Shared double room in restored monastery
  • Daily traditional breakfast and dinner, including wine
  • Daily painting classes and individual guidance
  • Excursion to Siena
  • ½ day painting excursions to nearby plein air settings and hilltowns (San Gimignano, Radda, Volterra,…)
  • Pick up from Florence train station at 3:30pm on arrival Saturday
  • Transfer to Florence station or airport on final day

Does Not Include:

  • Airfare
  • Lunch (lite lunch will be available for purchase at San Fedele on days we are not out on excursion)
  • Art supplies
  • Independent meals and sight-seeing
  • Gratuities – much appreciated by your hard-working staff.

To Register:  just click on the Sign Up Now button.  A 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 August 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.

Painting in the road to San Fedele


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.

Common/Studio space in the ex-chapel

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 $575.

2 Jr. Suites for a minimum of 2 people are available for a supplement of $275 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.

The upper pool at San Fedele

Florence 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.

Above the Ponte Vecchio, photo by Andy Holtzman

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 1½ 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 our Traveling to Italy link in the main menu bar above. Renting a car from all the major rental agencies is possible if you prefer to be more independent during the week.

If you have time, it is a nice treat to stay in Florence before the workshop starts.  It gives you a chance to get over jet-lag while at the same time allows you to see this incredible Renaissance City.  It is filled with incomparable artwork, architecture and history – not to mention great shopping.  Why not stop in for a few days.  (Look at our Travel to Italy tab above for accommodations suggestions.)


Florence: Sunrise Over City, photo by Anne Benvenuto


The side of the Duomo, photo by Andy Holtzman


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.