Tour, Explore and Paint

Paint in Tuscany October 12-21, 2026

Next Fall, would you like come along with me and spend time in a hilltop village in Southern Tuscany?

You'll find Tuscany to be a gentler version of itself in Fall. The weather will be crisp but not too cold, The grape harvest will be almost finished. The countryside will be all shades of glorious Fall colors. The big crowds of tourist will have gone home and the small family restaurants will be serving delicious seasonal food just harvested.

At night, after dinner, we'll return to our 4 star hotel and paint in front of the roaring wood fire place while sipping local wine or Vin Santo and nibbling on Italian contucci cookies.

We will spend 9 relaxing days and nights in Cortona, the hill top village that inspired the book and film, Under the Tuscan Sun. Even though Cortona has become prosperous since it became the location of a movie and book, it retains it's old world humble charm.

Cortona is filled with picturesque scenery for us to paint and spots to explore. There is an Etruscan museum, beautiful churches, a mummified Saint, cafe's to sit in and sip, old family restaurants, winding alley ways, Italian leather shops (need a new purse or wallet anyone?), gelato shops, a village square, a bounty of shops, a Saturday Farmers market, ages old wooden doors, windows with geraniums in their flower boxes and more....

Your trip will begin with our mini vans chauffeured by Gianmarco and his friends, who will drive us to our hotel in Cortona, The Villa Marsilli.

That first evening, you'll attend a welcome 4 course dinner prepared especially for our group by the hotel's wonderful chef in the hotel's dining room.

When you are not exploring Cortona,you'll hop into our chauffeured mini vans and explore and paint sights and villages in the region.

You'll take a small ferry to visit one of the islands in Lake Trasimento, where you can stroll thru the old village, visit a castle ruin or lace museum, hike a bit and enjoy a lunch of fresh fish.

You'll spend a morning exploring the splendid, small village of Montisi, then saunter over to the Cantina owned by my friend and favorite Tuscan Chef, Alessandro. In Cantina we will taste local wines he recommends and munch on a variety of Italian cheeses and meats.

You'll journey to one of the jewels of the area, Civita de Baneregio where you'll need to walk along a scenic bridge to reach this tiny village with only 14 residents.

On Sunday, you'll travel to Siena, the home of the horse race around the main square known as the palio, as well view its amazing architecture and perhaps visit the home church of Siena's patron saint, St. Catherine. On this particular Sunday, there will also be an antique faire in one of the squares for you to visit if you like old Italian ephemera and things. Siena also is home to an art supply shop, shoe and jewelry stores, a variety of neighborhoods and more.

Another landmark city you'll explore is the 3rd biggest city in Tuscany, Perugia, which is home to a university, the chocolate factory who make the Baci kisses, many interesting sights. A visit to Perugia's Stained Glass Window repair studio and museum has been arranged for your enjoyment.

You will be chauffeured back to Florence on the morning of October 21st where you might want to spend the day exploring and buying last minute souvenirs at the fun local markets. You'll need to enjoy a night in Florence if you want to fly out the next morning.

This trip includes transportation to and from Florence, lodging, all breakfasts, and daily art instruction.