Photo by: Kathleen Jacobs
Location: Italy

Italy Painting Tour of Tuscan Hill Towns

  • Plein Air Small Format Landscape Drawing and Painting workshop with Professional Tour Leader Kathleen Jacobs
  • Seven evenings in the Tuscan countryside, with grapevines and cypress trees
  • Tuscany’s medieval towns and villages: San Gimignano, San Donato, Greve in Chianti, and others, equally well-preserved
  • Departure limited to 12 participants to optimize your artistic experience
  • Optional evenings in the heart of Florence, for those wishing to explore the birthplace of Renaissance history, architecture, sculptures, and museums on your own.





October 8-17, 2025


9 days


per person, double occupancy*

*U.S. dollars based upon minimum of 8 participants. There is a small group surcharge of $400 if 5-7 participants. We try to accommodate travelers who request single accommodations, as well as travelers who are looking for a roommate. If a single room is requested (subject to availability), or if we are unable to find a suitable roommate, there is a single room surcharge of $625.

Tour Overview

We are proud to announce a special tour to Italy, led by artistic instructor Kathleen Jacobs.

This departure is limited to a maximum of twelve participants. While the emphasis is an artistic workshop, this is also a cultural journey, which we believe will enhance your ability to capture the essence of Tuscany in your work. Your guides will take you to locations you could not access on your own, including monasteries, churches, vineyards,...

We are proud to announce a special tour to Italy, led by artistic instructor Kathleen Jacobs.

This departure is limited to a maximum of twelve participants. While the emphasis is an artistic workshop, this is also a cultural journey, which we believe will enhance your ability to capture the essence of Tuscany in your work. Your guides will take you to locations you could not access on your own, including monasteries, churches, vineyards, and enjoy a cooking class overlooking a Tuscan valley.

One evening is included to overnight in Florence and prepare yourself for your time in Tuscany. Those wishing to add on evenings in Florence to enjoy time wandering on your own should contact Strabo Tours to secure rooms in the group hotel. The following are easy walking distance to the hotel: Ponte Vecchio, the Uffizi Corridor, and the Duomo. You can also immerse yourselves in the extraordinary art in the Uffizi and Academia Museums.

In this workshop students will paint in the open air of the beautiful Tuscan landscape. Each day we will look as Corot did, to interpret the soft color-palette of Italy. The hazy landscape paintings and poetic scenes of Jean-Baptiste-Camille Corot helped define plein air painting today. Like Corot we will seek to see and express the dreamlike quality of the color and light of Italy while staying true to our “first impressio” to capture the quiet dignity of the natural world.

We always welcome tour companions who are not artists. There are interesting aspects of Italian life waiting to be explored in every location. The quaint Tuscan villages offer wonderful landscapes, local markets, piazzas, and small shops to be enjoyed by all who might like to sketch, write, or simply appreciate the culture of Italy. The trip’s leisurely pace will provide ample opportunity to wander through medieval hill towns, and feast on the renowned regional foods and wines.

The accommodations that have been chosen combine simple elegance with excellent location. In Florence, you will stay at a small, family-run hotel, centrally located in a quiet neighborhood. In the Tuscan countryside, you will stay at a restored country villa, surrounded by a vineyard. It provides an absolutely perfect location for country walks and day trips to Tuscan hill towns and villages. You will have a light breakfast each day, followed by painting just outside your door with Kathleen three of the days. The other three you will depart for the day, enjoying the sights and sounds of the traditional Tuscan villages not far from your villa. Return to a traditional Tuscan meal in the evening.

Kathleen Jacobs and About this Class

 In this class students will start with intuitive sketches of the natural hills, trees and foliage of the Italian landscape. Students look carefully to make pencil compositional studies to settle into the view of such a special place. Working in any painting medium, students will make small intimate paintings in

one sitting. Like Corot, students will look to investigate composition, using form, shape, line, and color while working in nature. Emphasis will be placed on capturing the feeling of the landscape, without over analysis. We will use the historic color paint palette of Corot to express emotion.

Kathleen Jacobs will provide individualized instruction during plein air excursions, demonstrations, discussions, and presentations that will provide the format for an intensive exciting learning experience. Working small, participants will work to create work with a spirit of place. Her teaching emphasizes looking at the landscape and to understand the formal elements of painting, shape, color, space, form while responding to the grace, order and beauty that is in front of you. There will be ample opportunity to discuss each other’s work and to discuss other international painters throughout history to enrich our experience in Italy.

I took a workshop from Kathleen Jacobs this past summer in Gloucester, MA and am still thanking her for the invaluable painting tools I took away from the week. Kathleen is very knowledgeable about painting and drawing. The days flew by as she made painting a fun adventure at some beautiful, interesting spots in the area. We worked with a view finder every day to produce many thumbnail sketches, keeping in mind the form and structure of the landscape.  We then worked with a selected thumbnail to produce a painting. Working small placed an emphasis on simplicity and finding the structure of the landscape. This process, thumbnails and working small, allowed us to produce several paintings each day.  It really helped me make better decisions about my paintings. People in the workshop came from all skill levels and Kathleen successfully worked with each and every one of them. The group was very giving and if someone needed some paint or forgot something we all pitched in. Landscape painting is a tough endeavor and Kathleen made it a fun and accessible process and brought the group together. I highly recommend her as an instructor and cannot wait to take another workshop with her.


Tour Itinerary

October 8: Home

Depart on your overnight flight to Florence. (Meals on plane)

October 9: Florence

You can arrive at any time today at Florence Airport (FLR), everyone will take a taxi to the hotel. Use the afternoon and evening to rest, relax, and prepare for your week of painting in the Tuscan countryside. If anyone wishes to add on evenings in Florence on your own, contact Strabo Tours as soon as possible to secure availability. Overnight Florence

October 10-16: Tuscan Hill Towns

The group will depart with your local guide after a light breakfast to begin your journey at a lovely winery outside the city. Enjoy a wine tour, tasting, and light lunch with your local guide. Afterward you will depart for your villa. Get settled into your environs with an introductory meeting and prepare your supplies for the week. Each evening you will have a home cooked dinner at the villa.

You will enjoy three days at your homebase, with plenty of space and time to paint the villa, rolling hills, and vineyard right outside your back door. The other three days you will travel with your local guide to various hill towns, such as Greve in Chianti, the famous San Gimignano, and San Donato with a cooking class and lunch. You’ll have a different perspective in each town, taking time to set up your materials and paint various scenes alongside Kathleen and your like-minded travelers.

You will appreciate the contrast between the city of Florence and the Tuscan countryside. Today, more than sixty percent of Chianti remains forested, as there are strict limits on how much land can be cultivated.

San Gimignano is one of the most picturesque of the Italian hill towns, known as the “city of the beautiful towers”. Fourteen of the seventy original towers remain, giving the town a striking appearance. Tuscany (Breakfasts and dinners daily, one lunch is included at a local vineyard, one lunch at San Donato cooking class, and three lunches at the villa.

Please note: The art of enjoying an Italian meal can take time. You will have two lunches on your own in Chianti and San Gimignano. If you prefer to grab a light bite and meet with the group later, feel free to request time and place to meet your leader later in the day.

October 17: Florence - Home

After breakfast you will depart for Florence. Individuals can be dropped at the train station or airport for your departure (flight departure time should be no earlier than 11AM or after is best to avoid private transfers, 90-minute drive to airport). (Breakfast)