Fearless Watercolor in Tuscany
Jan Guarino
September 19 - September 26
$3750An Artist’s Journey Through Color and Courage

Join Jan for a week of art instruction, dining, touring, and exploring as we paint our way around Tuscany. Our focus will be on our beautiful surroundings, interpreting the landscape, and simplifying to achieve fun and exciting paintings. Each day will be a demonstration with a guided discussion of composition, where to place your focus, colors best to use and why, watercolor techniques, all while holding onto and growing your own personal style. Learn to be fearless!
Watercolors may feel intimidating at first. To be successful, you need to know how to control and give up control all at the same time. It should look and feel effortless, yet it takes an understanding of the medium.
In this week-long workshop with artist and educator Jan Guarino, explore one of the most important aspects of this medium, the element of surprise that happens when you get out of the way and allow the paint to move in water. Jan says that watercolor is all about how the paint flows and what happens in its wake. Deciding to control it or allow it takes time, patience, and practice.
This workshop will be centered around not just documenting a space in time, but interpreting the essence of the land. By studying the light, students will develop a greater understanding of their own painting knowledge, building skills they can develop in the field and take on future adventures forever. We will also be sure to take time each day to explore the towns, the wine and foods, and all the area has to offer.

Meals and our “Home” 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 each evening.
Breakfast is served buffet-style. You are free to eat indoors, out on the terrace, or in the garden – or go to town to enjoy a cappuccino with the locals! There is a lovely private pool at the end of the garden, which makes for the perfect end to a long day of painting. The villa is across the street from a historic castle and within easy walking distance of the town, where there is a grocery store, cafe, restaurant, and even a weekly outdoor green market. You can easily be independent to meet and interact with the locals!
Other Activities:
- Day trips to Pienza, Montalcino, and Montepulciano
- Truffle dinner at Donatella’s
- Visit to local sculpture garden Bosco della Ragnaia
- Visit to local, family winery Sasso di Sole – one of the few wineries that make Orcia, Rosso di Montalcino and Brunello wines
- Pizza dinner with Andrea
- Drive through stunning Crete Senese

Price: $3,750 p/p; non-painters $3,450
Optional supplement: $485 for single room, limited availability
$500 deposit due upon registration. Final Balance is due by July 16th.
Includes:
- Shared double room with private bathroom in villa (single room available for a supplement)
- Daily traditional breakfast and 7 dinners (including wine) prepared by our personal chef
- Truffle dinner at Donatella’s
- Visit to local winery
- Daily watercolor classes and critiques with Jan
- Excursions to nearby towns, Pienza, Montalcino, and Montepulciano
- Transportation and guide for all local excursions
- Pick up from Florence train station at 3:30 pm on Saturday
- Transfer to the train station in Buonconvento (not Florence) on the final day
Does Not Include:
- Airfare
- Gratuities (we suggest €10-20 per guest per day as a guideline)
- Independent meals and sightseeing

To Register: 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 online 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 before the workshop with information about Italy, a supplies list, and an electronic invoice for the balance. Final Balance is due by July 16th. 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.
Cancellation policy:
$500 deposit is non-refundable. For cancellation:
- 60 days prior to workshop, full refund due less non-refundable deposit.
- 30-60 days prior to 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.

San Giovanni d'Asso

Where We'll Stay: This is part of our new Il Chiostro Nobile series. We will be hosted for a week in an authentic, elegantly appointed villa that was at one time home to a noble Italian family. The palazzo includes a formal garden and, private swimming pool with inspiring vistas. Inside, there are 8 twin, double, or single bedrooms in the villa, each with a private bathroom. The rooms are decorated in authentic, elegant family antiques.
Common spaces include 2 elegant living rooms, a terrace overlooking the garden, a large fireplace, a kitchen, and a formal dining room.
The villa is across the street from a castle and within easy walking distance of the small town. You can easily be independent to meet and interact with the locals.

The Villa: a 13th-century manor house situated on a hillside in a small town with views of the Val d'Orcia. Owned by the current family for 102 years, it was gracefully restored in the 19th century with comfortable period furnishings. The rooms are bright and airy with high ceilings and beautiful views out to the gardens and the valley beyond. Bedrooms are elegantly appointed, each with a private, modern bathroom. Because we will be the exclusive residents at the villa during the program, the experience will be intimate, like living in our own Italian mansion. Our meals will be shared in the formal dining room, on the terrace, or in the garden. All living quarters of the villa are on the second floor, accessible only via a staircase.
The Grounds: the setting is extraordinary, overlooking the valley towards the Brunello wine country. There is a formal garden with a pool, lounge chairs, a shade arbor, and plenty of seating for outdoor meals. The Villa is an easy walk through the facing castle (now the museum of truffles) to the quiet village of San Giovanni d’Asso.
The villa and grounds consist of:
- 8 twin or double bedrooms, each with a bathroom, either ensuite or next door.
- A dining room and breakfast area
- Large terrace with tables
- 2 sitting rooms
- Wi-fi internet access
- Heat or air conditioning as necessary
- A large private formal garden area with fountains and, seating area
- A private pool at the garden edge with a valley view
- There is a changing room near the pool with a WC
- Air conditioning or ceiling fans in bedrooms
- Very quiet setting in a small village
Additional Photos of San Giovanni d'Asso:
Twin bedroom
Dining Room and Living Room in the Villa
The Town: San Giovanni d’Asso is in the Siena section of Tuscany. It is famous throughout Italy for its production of truffles. Small and quiet with fewer than 1,000 residents, the town has a café, grocery store, 2 restaurants, several historic churches, and a weekly outdoor market. A very special addition is the beautiful botanical gardens “Il Bosco della Ragnaia” (laragnaia.com/EN/) created by an artist who chose to turn his talents from painting and sculpture to designing and maintaining this beautiful space that is open free to the public.
The Area: San Giovanni d’Asso is 30 km southeast of Siena in the area known as the Crete Senese (see photo below). Pienza and Montalcino, and the famous Brunello wine country, are easy day trips.
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 the first day of the program.
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 can take either the shuttle bus (Volainbus) to the center (20 minutes) or the new tram, right outside the airport entrance (€1.50).
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 the last day of 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 allowing 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.)
Travel Agents & Insurance: Over the last few years, the way we travel has undergone significant changes. For that reason, we now encourage everyone to use a professional travel agent when arranging their trips. Travel agents save you time and stress by handling all the details and tailoring your itinerary to your needs. One of the most important services they offer today is helping you choose and enroll in the right travel insurance program. With COVID and the continued possibility of schedule changes or postponements, travel insurance has become essential, and selecting the right plan on your own can be overwhelming.
If you encounter any issues during your travels, your agent can provide quick support and solutions, taking the pressure off your shoulders. While booking through online sites like Expedia or Hotels.com may seem more convenient or less expensive, they offer little help if you need to modify your plans. A travel professional, on the other hand, is there to assist you every step of the way, ensuring a smooth and worry-free travel experience.
If you choose to Go It Alone, we highly recommend taking out travel insurance for the trip in the event of any unforeseen obstacles to your travel. We recommend Travelex (800) 504-7883 or Travel Guard International (877) 901-7599.
The Food: For us at Il Chiostro, helping our guests experience the food in one of the earth`s richest, most sensual areas is our pleasure. This area is part of Italy's famous wine and olive oil-producing region, but is specifically famous for truffles. Here we want to expose you to the wonders of simple Italian cooking. Each program at our villa in San Giovanni will have a personal chef. They use seasonal, organic products, locally produced by small farms and family shops. Tuscan cuisine is a simple art that has been refined over the centuries to surprise our palates while the wine comforts our souls. Come explore what food can really be all about.
An excerpt from a recent article in the NY Times (February 2013):
The diet that seems so valuable is our old friend the “Mediterranean” diet. It’s as straightforward as it is un-American: low in red meat, low in sugar and hyperprocessed carbs, low in junk. High in just about everything else — healthful fat (especially olive oil), vegetables, fruits, legumes, and what the people who designed the diet determined to be beneficial, or at least less-harmful, animal products; in this case, eggs and low-fat dairy. This is real food, delicious food, mostly easy-to-make food. You can eat this way without guilt and be happy and healthy.
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:
Art - San Giovanni d`Asso is located near 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 wine-growing region, synonymous with the most famous wine that Italy produces - Chianti. 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.
Food - cucina 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.

Jan has taught FEARLESS WATERCOLORS at the Art League of Long Island and The Artists Studio at Chelsea Mansion. Since March 2020, however, she has taught exclusively online and now reaches students from all over the US and internationally. Every year, Jan does a 4-day workshop at the Landgrove Inn in Vermont and an Artists' Trip to Europe. Starting Fall 2021, she will be resuming in-person classes at the Firefly Artists' second floor in Northport, NY, where she also exhibits and sells her paintings.
As a watercolorist, Jan longs to embrace all the wonderful things this medium has to offer, blossoms, drips, unexpected things that happen - lost edges, movement of pigment. Her comment:
I want to keep them all to remember that it is very much like life itself. Most artists feel that this medium is difficult to control and the most challenging to paint with. But I feel the total opposite of this. I long for all of the uniqueness and beauty watercolors have to offer, and to leave room for the viewer to fill in what may be missing or nearly suggested.
As a teacher, Jan loves to share this passion for watercolor techniques, theories, and joy with all of her students, hoping that they find enjoyment in interpreting their world with paint, splatters, drips, and color by embracing the unexpected and unplanned.
Jan has exhibited at the Heckscher Museum, the William Reis Gallery, the Huntington Arts Council, the Long Island Museum, the Art League of Long Island, the Art Guild, and is a permanent artist at The Firefly Gallery in Northport, NY.
Jan graduated from the Fashion Institute of Technology and has been a graphic artist designing marketing materials for businesses for 45 years. Recently retired from that, she looks forward to focusing entirely on painting and teaching.
Artists Statement:
Every painting I choose to paint focuses on the question … what drew me to this subject? As I move through this question, I look through a filter that asks what’s next and then go where the answers lead me. The subject may be a place I visited during my travels, I will be called to a particular photo, or a painting I started en plein air. It may be a photograph someone shows me of a person, a child, a couple that captured a moment, an expression, a posture. But when I see it, there is a moment where something grabs me and causes me to pause. I am overcome by a stirring and a knowing that I must paint it.
I don’t choose my subjects as much as they seem to choose me. My intention is always to create an unexpected depiction of the subject, a colorful interpretation, not a literal translation. I enjoy using this unusual color palette to bring you into the painting, and though you may have seen that place before, I wish for you to feel you are seeing it through a different lens for the very first time.
Website: https://www.janguarinofineart.com/





















