Tuscany

The place where heaven meets earth

Tuscany Plein Air with Painting in Paradise

June 2-9th 2026 7 nights

Don’t miss this opportunity to paint the Timeless Beauty of Tuscany – With Painting in Paradise, your trusted source for amazing plein air trips!
All-Inclusive Plein Air Retreat to Tuscany, Italy

Come and paint and we take care of the rest!

Featuring four nights at Hotel Castello di Leonina Relais which was once a noble residence. This 13th-century castle is set in Asciano and has beautiful views of the hills. It features a wellness corner, a Finnish sauna and a swimming pool with hydromassage. This hotel is highly recommended by one of our guests who will be attending. She raved about the hotel and how beautiful the grounds were.

Hotel Relais II Chiostro-3 nights

A 4 star quaint historic hotel which was an ancient 13th century convent.

Located right in the historic center of Pienza, a Renaissance town designed by Bernardo Rossellino by the wish of Pope Pius II Enea Silvio Piccolomini, with its hanging gardens overlooking the Val d’Orcia, the Relais Il Chiostro di Pienza.

Join acclaimed artist Gordon Breckenridge for an unforgettable all-inclusive plein air retreat set in the heart of Tuscany. Immerse yourself in the golden light and rolling hills of Italy’s most inspiring landscapes as you paint ancient hill towns, olive groves, and the iconic towers of San Gimignano.

This exclusive retreat offers more than just painting—it’s a full sensory experiences. With panoramic views, gourmet cuisine, and peaceful surroundings, it’s the perfect setting to relax and create.

What’s Included:
🎨 painting instruction & demos with Gordon Breckenridge. All locations will be close to restrooms.
🏰accommodations, including nights at Castello Leonina and Hotel Relais II Chiostro
🍷 Local wine, Tuscan cuisine, and private dining experiences
🚌 All ground transportation to painting sights and activities

Whether you're an experienced painter or seeking fresh inspiration, or even a beginner, this retreat offers a rare chance to grow your skills in a truly magical setting—with every detail taken care of.

Limited spots available. Reserve yours now and let Tuscany’s timeless charm awaken your artistry.

About the Teacher/Artist

Gordon Breakenridge is a renowned Italian painter and Plein Air artist who has sold over 500 paintings and thousands of prints of his artwork.

He has had his own gallery in San Gimignano and now in Sienna for 35 years total.

Gordon grew up in Canada and then moved to Florence and graduated from the Academy of Fine Arts in Florence in 1975, focusing on classical drawing and charcoal painting under the renowned teacher Nerina Simi at the Florentine art school founded by her father, who had studied with Jean-Léon Gérôme in Paris in

1870. Here, I learned to paint "Beyond the Eyes." I learned to detach myself from the details, to embrace the nature hidden in plain sight. To paint with light, this ineffable and elemental force. Light.

Day one

Hotel Relais 11 Chiostro di Pienza

Located right in the historic center of Pienza. According to Gordon this area is one of the prettiest places to paint in Tuscany. It is the quintessential Tuscany with rolling hills.

We will meet at 5:00 pm at the hotel for our welcome party, cocktails, non alcoholic drinks and a pizza party. Experience the essence of Tuscany with a welcoming shot of Lemonchello.

Day 2

Breakfast at your leisure

9:00 am

Start with classes on drawing and mixing colors to learn Gordon’s techniques.

Lunch and then off to plein air paint.

Dinner at hotel or other restaurant

Day 3

Breakfast at your leisure.

We will do a portrait painting lesson at the hotel and then pack up and have lunch on site. If you prefer to Plein air paint instead of portraits you may. You may also continue portraits during our Plein air sessions if you choose to do so as Gordon has a lot of portrait painting experience.

Then head to Sienna to see Gordon’s gallery and get inspiration. There will be some time to walk around Sienna and shop.

After that, we will head to Casale De Leonina Relais.

Late afternoon informal plein air session on the deck of the hotel or just relax.

Dinner at Leonina.

After dinner chocolate walk and explore the grounds of the hotel.

Day 4

Breakfast at your leisure

Plein air paint in the morning

Lunch

Afternoon

Go to Montepluciano for some wine and olive oil tasting. Visit the beautiful town and do some shopping. Montepulciano is a charming hill town perched on a 605 m limestone ridge in the province of Siena, southern Tuscany, maintaining its medieval layout blended with Renaissance.

Renowned wines: Montepulciano is celebrated for its Vino Nobile di Montepulciano (a DOCG wine), along with Rosso di Montepulciano and Vin Santo

Dinner back at Leonina.

Day 5

Breakfast early and off to San Giarmano to tour the town.

We will then paint in San Giarmano with Gordon.Lunch on site.

Before we leave town, we will have gelato at the famous award winning Gelateria Dondoli.

Dinner at Leonina or on the way back.

Day 6

Breakfast and off to a medieval city to plein air paint with Gordon at another location.

Lunch to be served while we paint.

Dinner Cooking class.

Day 7

Breakfast at your leisure. Choose between a silver jewelry making class in Chianti where you will make a piece of jewelry to take home, or a pasta and Tirramassou cooking class in Sienna, or enjoy a massage or spa treatment at the hotel. There may be other options as well.

Lunch will be where you are on your activity. Then back to Leonina Relais for a plein air session at Leonina hotel.

Or just enjoy the pool at the hotel if you would rather relax.

Festive last dinner

Day 8

Breakfast and viewing of all the paintings and prepare to leave to the airport or an added on journey.

If time permits you can also have a swim or paint a short while on your own.

How to get to Pienza

You can fly to either Florence which is closer or Rome. Florence is about 1.5 hours and Rome is 2.5 hours.

We can arrange a private car transfer from either airport for about $75 one way.

Cost:

2 painters sharing a room $5,695 each, please ask about rate for no l

Single painter $6,759

$2,000 deposit upon booking. Balance due two months prior to the trip.

Rooms are private hotel rooms with private bathrooms with either one bed or two beds.

Please note that travel insurance will be required as this is a non-refundable trip.

Please contact:

Brandon Hughbanks
Senior Travel Insurance Specialist to book your insurance directly. You may also use your own insurance provider if you desire. It must cover the dollar amount and health coverage.

Toll Free:1-866-979-6753 Ext. 3636
Direct: 402-343-3636
Fax: 402-343-9959
CA License # 0I86487

SMS CA License Number 0802699
bhughbanks@travelinsurancecenter.comwww.travelinsurancecenter.com

Also if you would like to have your airline reservations made by a well recommended travel agent you are welcome to call below. She charges $100 per person per ticket.

Julie-Ann Skalko, CTC

CADENCE

7701 Hershel Ave, La Jolla Ca 92037

1-858-551-8881

1-800-92-JULIE

Julie@cadencetravel.com