TRAVEL JOURNALING IN TUSCANY with Simon Roberts

Join Simon for a once-in-a-lifetime travel journaling experience in Italy as you learn his best tips and techniques for drawing and painting everything from your morning cappuccino to the classic, Tuscan landscape.

ABOUT Simon Roberts

After many years working as a commercial artist, in the UK, Munich, Germany, and Vienna, Austria Simon Roberts now lives in the south of France with his wife Monica, and their springer spaniel, Millie.

Simon is a keen watercolor artist and tutor with a loose journaling style which he developed during his many travels through Europe, the Middle East, India, and Africa.

It was while on a 7-month solo motorcycle trip overland to Kathmandu, Nepal, Simon began adding illustrations to his Travel Journals. “I would often see sights on the road during the day which I then sketched into my journal from memory during the evening…”

Simon’s annual watercolor workshop in Tuscany combines his easy-going style with the endless inspiration of the Italian countryside.

ABOUT Simon Roberts

Having studied Technical Graphic Art, Simon has a comprehensive knowledge of perspective techniques which he will unravel for you through this all-inclusive workshop in Italy. “It’s a vital part of sketching on the road – whether you’re painting landscapes or village scenes – or even a simple glass of wine”.

Simon’s approachable manner and keen sense of humor are an intrinsic part of his tutoring style. He will show you how to capture a scene quickly and simply whether you’re exploring a medieval hill town or taking in a countryside panorama. With his expert guidance you’ll learn to create beautiful, visual memories of your travels that you can keep forever.

YOU’LL LEARN How To…

• Draw and paint everything from a glass of Prosecco to a dramatic Tuscan landscape!
• Unravel the mysteries of perspective: One, two, and three point.
• Draw quick thumbnail sketches before tackling bigger pieces
• Sketch a complicated scene – simply
• Design page layouts that bring your watercolor journal to life
• Gain confidence with watercolor washes
• Add dramatic light and shade to bring your sketches to life
• Work with a limited range of colors to create a mood
• Choose which scene to paint
• Add text or notations to your pages
• Use a wide range of color to bring depth and richness to your painting
• Pack your art bag with the minimum equipment necessary for a day’s painting
• Know when your painting is finished and you can put your brush down!

ITINERARY

Day 1: Arrival

• Welcome and trip orientation with Simon
• Aperitivo, dinner

Upon your arrival at Rome Fiumicino Airport, our private drivers will transport you to the Italian countryside, and your boutique hotel accommodations in the unspoiled village of Città della Pieve. After check in, you’ll enjoy a walking tour of the historic center of the village, with trip facilitator, Pamela Haack. Then it’s off to the art studio for a workshop orientation with Simon.

Afterwards we gather together for a welcome aperitivo, followed by a delicious regional-style dinner prepared by Chef Vito. 

Day 2: Città della Pieve

• Instruction with Simon, Renaissance walking tour
• Breakfast, lunch, dinner

This morning, after a delicious, buffet breakfast, you’ll join Simon for both studio and on-site instruction, as you learn specific sketching techniques and approaches for creating your Italy travel journal. Lunch today is served at our friends’ friendly cafe.

This afternoon you’ll join Simon for some small group and individual instruction, followed by a “Renaissance walking tour” that includes of the town’s 15th century cathedral, featuring masterpieces by Renaissance artist, Perugino, who was born here in Città della Pieve. Plus the church’s interior decorations are a unique inspiration for your travel journal! This evening you’ll enjoy aperitivo at our friend’s cafe, followed by dinner cooked alle brace (over coals) at a local trattoria.

Day 3: Painting at the Vineyard

• Instruction with Simon, vineyard tour & painting
• Breakfast, lunch, dinner

This morning, after breakfast, our drivers will be transporting you through the stunning countryside to a local winery where you’ll enjoy a private tour – inside and out – followed by a morning of drawing and painting in the vineyard with Simon. Plus the cypress-lined lane that divides the property creates a classic Italian scene. Lunch with wine from the cantina will be served up right here, under the shade of a bay tree.

In the afternoon you’ll have free time to relax or explore on your own, followed by an afternoon of small group and individualized instruction with Simon. This evening it’s off to a a favorite trattoria for a Mediterranean-style dinner.

Day 4: Città della Pieve and Pasta Making

• Instruction with Simon, pasta making lesson
• Breakfast, lunch

This morning, after breakfast, you’ll enjoy free time to explore or sketch on your own, then it’s off to our friend, Cristian’s, bistro for a delightful pasta-making lesson that includes a peek inside his private wine cantina. Lunch follows – featuring your handmade pasta, of course!

After lunch, and a brief rest, you’ll join Simon for an afternoon of instruction – perhaps painting one your favorite medieval alleyways. This evening you’ll enjoy aperitivo at a nearby cafe.

Day 5: Pienza

• Excursion to Pienza, instruction with Simon on location
• Breakfast, dinner

This morning, after breakfast, it’s off to the charming Tuscany town of Pienza, situated in the spectacular Val d’Orcia – one of the region’s most painted and photographed areas. Here you’ll explore and paint, with Simon’s expert guidance. Plus you have some free time to shop and find a spot for lunch on your own.

In the afternoon it’s back to Città della Pieve for some free time before we gather together and head to a private home for aperitivo and pizza.

Day 6: Città della Pieve

• Instruction with Simon, farewell dinner
• Breakfast, dinner

This morning, after breakfast, you’ll enjoy a final session with Simon drawing and painting along the picturesque avenues of Città della Pieve, or even in the garden at a private home. Lunch today will be on your own.

In the afternoon, it’s back to the studio for a final, wrap-up session with Simon, followed by a celebratory aperitivo. This evening you’ll enjoy a delicious farewell dinner prepared by Chef Vito.

Day 7: Departure

Early morning transport to Rome Fiumicino Airport.

ACCOMMODATIONS ~ Boutique Hotel Vannucci

Hotel Vannucci began as a project of Vittoria Spinola, daughter of King Vittorio Emanuele II, who fled Pisa (and an arranged marriage with her elderly husband) to start a new life with her lover in Città della Pieve. Here, she and her soon-to-be new husband, Paolo, built two villas that became luxurious holiday accommodations for wealthy Romans vacationing in the countryside. In 1903 one of the villas became Hotel Vannucci, and today it maintains the elegance and refinement of its inception, with luxurious sleeping rooms, marble bathrooms and inviting gardens. A stay here is truly special, nestled just outside the medieval walls of the historic, and unspoiled, village of Città della Pieve.

VIEW Photo Gallery

WHAT’S INCLUDED

• Daily individualized and small group instruction with Simon Roberts
• A4 personal spiral bound notebook
• Paints, palettes and brushes for the duration of the workshop
• 7 days/6 nights stay at Boutique Hotel Vannucci
• Private transportation service pick-up on arrival and departure days (Rome Fiumicino Airport)
• Private transportation service to/from all towns and sites included in the itinerary
• All breakfasts
• Most lunches  
• 5 regionally inspired dinners, featuring local wines
• Excursion and painting at a winery
• Excursion and painting in Pienza
• Renaissance walking tour
• Pizza night!

Not included: Airfare, meals, alcoholic drinks, or transportation outside of that which is specifically listed in the trip package, gratuities for hotel staff and drivers

The Unexpected is Part of the Journey: Sometimes unexpected things come up. If there is unscheduled closing or schedule change, we carefully pivot to include something that is equally as wonderful and interesting, so that the quality of your experience is never at risk. ☺️

DATES AND DETAILS:

• Dates: June 22-28, 2025
• Trip Price: $3,345-$3,895 (select room type upon booking)
• Room Descriptions:
  • Single: Single occupancy, single bed, private ensuite bathroom
  • Classic: Single occupancy, double bed, private ensuite bathroom with walk-in shower
  • Superior: Single occupancy, double bed, private ensuite bathroom with tub/shower combination
  • Deluxe: Double occupancy, double bed or two singles, private ensuite bathroom with tub and shower (specifically for couples or friends traveling together)
• A $700 deposit is required to book your space on this trip
• View our Terms and Cancellation Policy
• Arrival/Departure Airport is Rome Fiumicino

BOOK NOW