Eat Paint Love Tuscany
Rebecca Zdybel
October 10 - October 17
$4700Let’s slow down and savor life the way they do in Italy

This will be a week of getting to know authentic and beautiful Tuscany through touring, painting, and eating our way around this gorgeous part of Italy. Extra opportunities to enrich your experience will be available through painting and optional activities such as cooking, hiking, cycling, or taking a vintage car for a spin. Painting opportunities will abound, whether you prefer plein air or painting in the comfort of our permanent studio. Painting trips always attract interesting people, and together we take day trips to visit beautifully authentic and wonderfully medieval towns in the region of Italy known as Tuscany.
In many of our stops, Rebecca will paint/photograph, or draw on site. She will offer art lessons and regularly schedule studio time, making every effort to be available to assist those who choose to paint or draw during the trip. We would encourage planning to paint in a sketchbook to minimize equipment requirements. Our priority will be to see our destinations and enjoy them, enhancing the experience through art if desired. For those who would simply like to visit Tuscany and shop or photograph their way through this beautiful part of the world, we can assure you that the sites you will visit will be like a visual candy store!

A Note from Rebecca: After many trips to this region, I know that Tuscany continues to charm and reveal itself to me again and again in ever-surprising ways. It’s just that special! Our venue is a refurbished Tuscan castle. It will be the perfect place to call home while in Tuscany. It’s convenient, romantically old and beautiful, and fully modern in terms of amenities. I love being able to tour and paint the days away without having to answer the question: “What will we do for dinner?” Every night we will be treated like kings and queens by the Castel’s private chef. Among the sumptuous gourmet meals, there will be some special dinners. We will tuck into an evening of the comforting and heartwarming pizza extravaganza and another evening of a typical Tuscan BBQ. All this is coupled with award-winning wines produced by La Leccia and the surrounding vineyards. Sitting around a table, eating good food, and drinking good wine is always a delicious bonding experience.
Painting is optional but not required. This week will be an experience with painting and lessons as an option.
Who should consider spending a week with us in Tuscany?

- Come if you like food and eating authentic farm-to-table fare. (Farm-to-table is nothing new here; Tuscan chefs have always cooked this way!). Dinners will always be eaten as a group, and lunch will allow you to seek out local favorites wherever we are. Lunch is always a priority, and since we have drivers, we can safely enjoy sampling different local wines.
- Come with us if you have an interest in painting or drawing, or photographing beautiful sites while you travel. Plein air painting opportunities and studio time will be available for those who choose to take advantage. As your instructor on this trip, I’ll give lessons and offer tips on how you can approach making art while we travel. I have lessons planned, lots of references you can access, and I can help you find good locations for painting or drawing.
- Come with us if you enjoy wine! This region of Chianti is famous for its wines (including the Super Tuscans). Our wine is included with our meals every evening. It’s delicious, and many are preservative-free. We will also be touring a local winery. Their wine, their food, and their ambiance are all worth seeing.
- Come with us if you’d like to tour other parts of Europe or Italy, before or after our week together. Feel free to add on to your travels at both ends of the trip. So long as we all meet at the appointed time in Florence on the first Saturday afternoon, your itinerary and travel plans are your own.
- Come with us if you want to slow down and savor life, the Tuscan way! I want more of this kind of living in my life! Bringing a group of like-minded people along with me makes it an even more ideal experience.
I can assure you that my students tend to be positive, bright, adventurous, artistic, kind, and fun. If that sounds like a group you’d enjoy, then I hope you’ll join me!
Additional Activities – In addition to the activities of the workshop, we will also see and explore this area of Tuscany with various excursions:
- Chianti winery tour and tasting
- Optional excursion to the local pottery factory
- Visit to open an open-air market
- Optional dinner at a local enoteca (wine bar)
- Massages available upon request, priced accordingly
We’ll return each evening to relax in our beautifully appointed and romantic Tuscan castle. After optional aperitivos or an Aperol spritz on the terrace, and dinner, we will have the chance to gather and enjoy some live music thanks to my husband, who loves to get the group singing while he plays guitar. Sometimes we are even serenaded by our Il Chiostro hosts. Every moment will not be scheduled. When we get to our destinations, I will let you explore things in your own way and let you know when to return for your ride back to home base. Andiamo! (Let’s go!) Join me for an Eat, Paint, Cook Tour of Tuscany… painting, drawing, photographing, touring, cooking, sipping, eating, and savoring all that this lovely region has to offer!

Here is what students are saying!
“Dear Rebecca, Thank you for providing such an exceptional trip…my dream come true! Your preplanning was so evident and made for a smooth, exciting week. It was enriching to have you as our guide, teacher, host, and traveling companions. You are examples of life “well lived” and sharing it with others… I wish you all the best, and will continue to savor these precious memories…” – 2014 Participant
“Rebecca, thank you for all the wonderful positive energy and encouragement you bring to class as a teacher and fellow artist. I am so enjoying all that is unfolding… It’s all inspiring, learning, and much-needed for me as an artist on so many different levels. You are a gift.” – A past participant
“Your personal touch makes more of a difference than you realize…you have lit the fire, and I look forward to all the gasoline you can muster …I look forward to that ROAR.” – A past participant

Price – There are three categories of shared double rooms that you can select from:
- Suite in Castle – $5,300
- Superior room in villa – $4,850
- Classic room in villa – $4,700
Optional single room supplement – limited availability:
- Suite in Castle – $1,000
- Superior room in villa – $900
- Classic room in villa – $800
$800 deposit due upon registration. Final Balance is due by August 6th.
Includes:
- Shared double room with private bathroom in villa (single room available for a supplement)
- Daily traditional breakfast and 5 dinners (including wine)
- Two special dinners – Pizza night and BBQ night
- Chianti winery tour and tasting
- Optional excursion to the local pottery factory
- Visit to open an open-air market
- Optional dinner at a local enoteca (wine bar)
- Massages available upon request, priced accordingly
- Daily classes and critiques with Rebecca
- 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 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

Here is a sample Itinerary: Please note that while this is a sample of what you can expect, activities can be subject to change.
- Saturday: Meet at Florence train station at 3:30 PM. Board the bus to Castello La Leccia in Chianti. Check-in/ Orientation first dinner.
- Sunday: Optional art Lesson with Rebecca in the morning, opportunity to paint/draw/photograph on location at Castello la Leccia. Non-painters can hike and explore, relax at the poolside, or visit the nearby hilltown. Afternoon BBQ. Optional evening excursion to a local family winery – tour/light dinner/wine tasting at the winery.
- Monday: Excursion to medieval Siena. Opportunity to draw/paint/photograph on site if desired. Shopping is plentiful here. Grab an independent lunch and people-watch in the famous Campo. Late afternoon studio time or rest time. Optional aperitivos before dinner. After dinner- music on the terrazzo.
- Tuesday: Excursion to the local market, where you can shop for a potluck lunch in the picturesque hill town of Monteriggioni. Shoppers can shop, and painters can take a moment to capture something for their sketchbooks. Group photo on the way home. After dinner, music on the terrazzo.
- Wednesday: Excursion to San Gimignano, medieval Pienza, or Montepulciano. Lunch on your own while in town. Optional aperitivos before dinner. After-dinner studio time.
- Thursday: Cooking lesson with a local Tuscan chef. We’ll go to his home nearby and cook in his kitchen. We’ll eat our lunch on his terrace and possibly walk to his cousin’s winery next door to sample their recent vintage. Optional afternoon excursion to a nearby hill town for shopping and gelato. Optional aperitivos before dinner. After dinner, music on the terrazzo.
- Friday: Optional art lesson and excursion to another Hill town (Castellina, Radda, Volterra, San Gimignano, or Siena). Independent lunch with optional shopping at a local pottery factory, which showcases its exquisite wares. Studio time, pool time, or hike time in the afternoon. Farewell exhibit and program in the evening.
- Saturday: Breakfast and departure for Florence and travel connections.

To Register: Click on the Sign Up Now button. 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 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 August 6th. 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:
$800 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.

We will be hosted for a week in an authentic, elegantly appointed castle and villa that was once home to a noble Tuscan family. The Castello la Leccia, perched high above the rolling hills of Chianti Classico, has been lovingly restored with a graceful balance of medieval architecture and modern comfort.
The property includes a formal garden, a panoramic swimming pool overlooking vineyards and olive groves, and a series of peaceful terraces where you can relax and take in the views. Inside, the castle is furnished with refined Tuscan antiques and artisanal pieces that preserve the warmth and history of the estate. The separate villa is more casual with 5 bedrooms on the second floor (no elevator), sharing a common space, kitchen, and dining area.
The elegant bedrooms each have a private, modern bathroom. The rooms are decorated in traditional Tuscan style, with terracotta floors, beamed ceilings, and soft natural tones, each offering a unique view of the surrounding hills, vineyards, or the distant skyline of Siena.
Common spaces include a comfortable living room, a library corner, a terrace overlooking the valley, and a formal dining room. There is also an on-site restaurant and wine cellar, where the estate’s own organic Chianti Classico wines are produced and served.
The castle sits above the charming village of Castellina in Chianti, where you can find small cafés, artisan shops, and local restaurants. You can easily explore independently and experience daily Tuscan life at your own pace.

Castello la Leccia has evolved over centuries into an elegant residence. Restored by its current owners with care and authenticity, the castle maintains its original stone architecture while offering contemporary comforts and thoughtful design.
The rooms are bright and inviting, with high ceilings, handcrafted furniture, and views that stretch across olive groves and vineyards. Meals will be shared in the formal dining room, on the open terrace, or under the shade of trees in the garden. Expect classic Tuscan flavors prepared from locally sourced ingredients, complemented by the estate’s own wines.

The Grounds: The estate’s setting is truly extraordinary, surrounded by vineyards, olive trees, and cypress-lined roads that define the Chianti Classico landscape. The panoramic infinity pool overlooks the valley, providing a perfect spot to relax with a book or enjoy a glass of wine as the sun sets.
The castle and its grounds consist of:
- 12 elegantly appointed bedrooms, each with a private bath
- Dining room and breakfast terrace
- 2 sitting rooms and reading areas
- A panoramic infinity pool with lounge chairs and umbrellas
- Wi-Fi internet access throughout
- Heating and air conditioning as needed
- Expansive gardens and shaded outdoor seating
- Organic vineyards and olive groves on the estate
- A private wine cellar for tastings and tours
A peaceful hilltop location surrounded by nature, with views extending toward Siena.

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.
If you have additional questions regarding planning, please email info@ilchiostro.com or administrative assistant Lexi at lexi@ilchiostro.com.
Perched above the vineyards and olive groves of Castellina in Chianti, Castello la Leccia offers a front-row seat to everyday Tuscan life. This authentic Chianti village hums with warmth and authenticity, stone lanes that echo with history, cafés where locals linger over espresso, and little wine shops tucked under ancient arches. It’s the kind of place where time slows down, and a simple stroll feels like a step into another era.
Beyond the castle walls, the landscape unfolds in layers of beauty, the golden light over the vineyards, cypress-lined roads that wind toward Siena, Radda, and San Gimignano, and vistas that seem painted by hand. This corner of Chianti Classico captures the spirit of Tuscany at its most genuine: elegant, earthy, and endlessly inspiring.
From lazy afternoons in the piazza to day trips through the hills, every moment here offers a taste of the good life, one that invites you to savor, explore, and truly belong.


Rebecca is an award-winning artist and author from Myrtle Beach, SC. She has owned and operated Rebecca Z Artist Studio Gallery for the past 9 years.
As a signature member of the South Carolina Watermedia Society, she paints and teaches art in-person and via online classes.
As a self-proclaimed “late-bloomer,” she knows first hand how life enhancing the pursuit of painting can be! She loves to teach and hates to keep secrets, which means that she shares all she can, with the goal of helping her students to enhance their skills and their confidence.
In 2024, she co-authored a #1 Amazon Best seller titled “Inspiring Women- Purpose, Passion, and Power in Professionalism”.
For the past 12 years she has combined her art and love of travel to host international art/travel experiences.
Website: https://rebeccazartist.com/
Rebecca’s artwork may be viewed and purchased @ https://www.artworkarchive.com/profile/rebecca-zdybel
Her YouTube Channel: https://www.youtube.com/@RebeccaZdybel/videos
Facebook https://www.facebook.com/rebeccazdybel
Instagram- @RebeccaZArtist
Website: https://rebeccazartist.com/





