Travel Journaling in Tuscany with Simon Roberts, June 16-22, 2024

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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…”

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 Simon’s expert guidance you’ll learn to create beautiful, visual memories of your travels that you can keep forever.


  • Draw and paint everything from a glass of Prosecco in the café 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
  • 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
  • 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!


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 and Perugino

  • Instruction with Simon, Renaissance walking tour
  • Breakfast, 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 on your own (we’re happy to make suggestions) followed by some time to rest and recharge.

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: Murogrosso and Vineyard Visit

  • Instruction with Simon, vineyard tour + wine tasting
  • 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 will be served up right here, and includes a wine tasting of several of the cantina’s wines.

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 local restaurant for aperitivo and 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, followed by an option walk through the village to see the narrowest street in Italy! This evening you’re free for shopping, exploring and dinner on your own (of course we’ll have plenty of suggestions).

Day 5: San Casciano dei Bagni and Pizza

  • Onsite instruction with Simon, tour of archeological site
  • Breakfast, lunch and dinner

This morning, after breakfast, it’s off to the charming village of San Casciano dei Bagni, situated on a hilltop teaming with hot springs. Here you’ll enjoy a private tour of an astonishing Etruscan and Roman archeological site, followed by lunch at our friend, Daniela’s restaurant, nestled between the walls of the town’s castle.

In the afternoon you’ll have the opportunity to sketch with Simon along the town’s inviting avenues, with spectacular views over the hills of Tuscany. Afterwards, it’s back to Città della Pieve for some free time before we gather together to head to our friends’ pizzeria for dinner.

Day 6: Città della Pieve

  • Instruction with Simon, farewell dinner
  • Breakfast, lunch and dinner

This morning, after breakfast, you’ll enjoy a final session with Simon drawing and painting along the picturesque avenues of Città della Pieve, including window boxes overflowing with vibrant summer flowers. Lunch today will be served up at our friends’ inviting, outdoor cafe.

In the afternoon, it’s back to the studio for a final, wrap-up session with Simon, followed by a celebratory aperitivo in a private home. 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


  • 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
  • Visit to organic vegetable garden and plant nursery
  • Visit to archeological site
  • 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: June 16-22, 2024
  • Trip Price: $3,175-$3,675 (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