Tuscany Retreat 2025

Dates: 22 to 30 August – 10 spaces left

2 to 10 September 2025 – Fully Booked

Pronto!  Benvenuto.

We are going to Italy to paint, to see Michaelangelo, eat pasta, drink wine and travel! 

Tuscany is a region in central Italy known for its stunning landscapes, rich history, and cultural heritage. It is one of the most popular tourist destinations in Italy and is celebrated for its picturesque countryside, charming villages, vineyards, and historic cities.

Here are some key features of Tuscany:

Landscape:

Tuscany is renowned for its diverse and breathtaking landscapes. The region is characterized by rolling hills, olive groves, vineyards, and cypress trees. The countryside is dotted with medieval villages and farmhouses, creating a postcard-perfect scenery.

Tuscany is home to several iconic cities and towns. Florence, the capital of the region, is a cultural and artistic hub, boasting world-renowned museums, cathedrals, and architectural masterpieces. Other notable towns include Siena, Pisa (known for the Leaning Tower), Lucca, and San Gimignano, each offering unique historical and architectural attractions.  Tuscany has played a significant role in the cultural history of Italy and Europe. The region was a focal point of the Renaissance, and its cities are filled with art treasures. Florence is known for its art museums, including the Uffizi Gallery and the Accademia Gallery, which houses Michelangelo’s David.

Tuscan cuisine is renowned for its simplicity and emphasis on high-quality, locally sourced ingredients. Dishes often feature olive oil, fresh vegetables and pasta. Tuscany is also famous for its wines, particularly Chianti and Brunello di Montalcino, produced in the region’s vineyards.  Tuscany has a rich historical heritage, with numerous medieval and Renaissance-era buildings and landmarks. The region’s history is intertwined with powerful families, such as the Medici in Florence, whose influence left a lasting impact on art, architecture, and politics.

Overall, Tuscany’s combination of natural beauty, cultural richness, and culinary delights make it a captivating destination for travelers seeking a taste of Italy’s finest offerings.

Cortona Italy: A Jewel of Tuscany

Perched on a hilltop overlooking the stunning Val di Chiana, Cortona is one of Tuscany’s most enchanting towns. With its roots tracing back to the ancient Etruscans, this picturesque destination seamlessly blends history, art, and natural beauty, offering visitors a truly timeless experience.

The town’s medieval streets wind through stone buildings, charming piazzas, and artisan shops, each corner revealing breathtaking views of the surrounding countryside. From golden fields of sunflowers to rolling olive groves and vineyards, the landscape is quintessential Tuscany, as if plucked from a Renaissance painting.

Cortona is famed for its rich cultural heritage. Its ancient walls, which date back to the Etruscan period, still embrace the town, whispering tales of its storied past. The majestic Piazza della Repubblica, with its iconic Town Hall, is the heart of Cortona, where locals and visitors gather to enjoy the lively atmosphere. Nearby, the Cathedral of Santa Maria Assunta and the Church of San Francesco showcase exquisite architecture and sacred art.

For history enthusiasts, the MAEC Museum (Museo dell’Accademia Etrusca e della Città di Cortona) offers fascinating insights into the town’s Etruscan origins, as well as Roman and medieval artifacts. Art lovers will find inspiration in the Diocesan Museum, home to masterpieces like Fra Angelico’s “Annunciation.”

Beyond its cultural treasures, Cortona offers a vibrant culinary scene. Local trattorias serve up traditional Tuscan dishes like pici pasta, ribollita, and bistecca alla Fiorentina, paired perfectly with wines from the nearby Chianti region. The town’s lively markets and annual festivals, such as the Sagra della Bistecca and Cortona Mix Festival, celebrate its deep-rooted traditions and community spirit.

For those seeking tranquillity, Cortona provides ample opportunities for quiet reflection. Stroll through the lush gardens of Villa Bramasole, immortalized in Frances Mayes’ memoir Under the Tuscan Sun, or hike up to the Basilica of Santa Margherita, where panoramic views of the countryside await. Further uphill lies the Eremo Le Celle, a serene Franciscan hermitage surrounded by nature.

Whether you’re drawn by its history, art, cuisine, or simply the charm of a sun-drenched Tuscan town, Cortona captures the essence of Italy’s beauty and soul. It’s a place where time slows, and every moment feels like a celebration of life.

Food and Wine in Cortona

Cortona is a food lover’s paradise, offering the best of Tuscany’s rustic yet refined cuisine. The town’s trattorias and osterias invite you to indulge in the rich flavours of the region, often crafted with local, seasonal ingredients.

Signature Dishes:

Pici pasta, a thick, hand-rolled pasta, is a must-try, often served with cacio e pepe (cheese and pepper) or rich wild boar ragù.

Ribollita, a hearty Tuscan soup made with bread, beans, and vegetables, is perfect for a comforting meal.

Bistecca alla Fiorentina, the iconic Florentine-style T-bone steak.

Cheeses and Olive Oil: Cortona’s surrounding farms produce some of Tuscany’s finest pecorino cheeses, while the olive groves yield exquisite extra virgin olive oil. Many local producers offer tastings where you can savour these artisanal products.

Wine: As part of Tuscany’s renowned wine region, Cortona is celebrated for its Syrah wines, a grape variety that thrives in the local terroir. You can also enjoy robust reds like Chianti and refreshing whites like Trebbiano. Wine lovers will relish the opportunity to visit nearby vineyards and wine cellars for tours and tastings.

Dining with a View: Many restaurants and wine bars in Cortona offer outdoor seating with sweeping views of the Val di Chiana, making every meal a feast for both the palate and the eyes.

Art and Culture in Cortona

Cortona is a cultural gem, brimming with artistic treasures and historical landmarks that showcase its deep connection to the past.

Art and Museums:

The Diocesan Museum is a treasure trove of religious art, featuring works by Fra Angelico, Luca Signorelli, and other Renaissance masters. Fra Angelico’s Annunciation is a particular highlight, renowned for its luminous beauty.

The MAEC Museum (Museo dell’Accademia Etrusca e della Città di Cortona) takes you on a journey through time, from Etruscan artifacts like funerary urns and bronze sculptures to Roman relics and medieval finds.

Historical Sites:

The Basilica of Santa Margherita, perched high above the town, is a peaceful sanctuary dedicated to Cortona’s patron saint. The basilica’s interior is adorned with beautiful frescoes, and its elevated position offers panoramic views.

The Eremo Le Celle, a Franciscan hermitage, is a serene retreat nestled in nature, where St. Francis of Assisi once stayed. It’s a must-visit for those seeking spiritual inspiration.

Local Crafts: Cortona is home to talented artisans who create beautiful ceramics, leather goods, and textiles. Strolling through the shops, you’ll find one-of-a-kind pieces that make for perfect souvenirs.

Accommodation:

Hidden Oasis in the Countryside – Cortona

The villa contains an enchanting “secret garden.” Surrounded by breathtaking landscapes and wrapped in a serene, timeless atmosphere.  Whether you’re sipping a glass of wine or simply taking in the beauty around you, every corner invites you to unwind and reconnect with nature.

Inside, the house reflects a harmonious blend of rustic charm and refined elegance. Thoughtfully designed interiors, curated furniture, and unique decorative pieces create an ambiance of comfort and sophistication, immersing you in the essence of relaxation. Every detail has been chosen to enhance your experience and evoke the joy of an authentic countryside Tuscan escape.

Outside is a braai, pool and dining area, nestled within the garden. It’s the perfect setting to savour delicious meals while basking in the tranquillity of your surroundings.  There is a large fully equipped kitchen and dining area, patio, lounges and Wi-Fi.

Location:

Il Sodo is close to an important archaeological site with a park, 2 kms from Cortona. A wide range of winemakers and farms that produce one of the best extra virgin olive oils.

Getting around:

The nearest train station is Camucia /Cortona just 2 kms away.

The motorway exit is Valdichiana /Bettol. 

Transport:

Flights from Jhb to Florence airport are in the region of R20 000.00 or more.  Please remember the traveling time.  The earlier you book the better.  Skyscanner is the best app to look for possible flights – I prefer a Europe stopover rather than Dubai, but you may pay more.  The airport name is Amerigo Vespucci.  Remember that your flight probably needs to be booked on 20 August or earlier as the itinerary starts on August 22.

Car Rental:

The cheapest I found was on Skyscanner, but shopping for a good deal is advised.

Train:

There is no train station at Florence Airport, but an airport shuttle takes travellers arriving at the airport to the main train station, Santa Maria Novella or SMN for short. It takes about 20 to 30 minutes to get to SMN, then you can connect to a train to Cortona.  You can also take an uber from the airport to the train station.  Then I can fetch you from the Cortona Station.  The fast train that runs takes 2 hour, the normal train 2 hours.

LIVING:

Everyone buys for himself as a rule, but usually we share.

For breakfasts we can buy breads, butter, jams, cheeses, cereals, fruits, yoghurts and lunches and dinners pastas, sauces, salads or create our own “charcuterie board, which also features cured meats and cheeses, but can include different ingredients depending on the region.

Variety of ingredients: An “antipasto platter” typically includes cured meats like salami, prosciutto, mortadella, cheeses like mozzarella, parmesan, pecorino, olives, marinated vegetables, and sometimes even roasted peppers.

Itinerary

Date	Time	Activity
Day 0		Arrival after 2pm at Villa Please bring drinking water with you. (Italy’s water is fine to drink) The evening meal will be carbs, cheese and wine that I will provide.
Day 1	9am	We drive to Porto Colonia, Cortona (parking is a problem when we go too late).
	10 am	Grab a sandwich or ‘panino’ and buy groceries for the week at La Bottega di Via Dardano and return your shopping to the car(s).
	11am	We will visit the Piazza Galleria, and you will have a little time to stroll on your own or with me.
	1pm	Lunch in Cortona – La Bucaccia – Da Romano
	2pm	Drive back and enjoy a riposo – a siesta.
1	4pm	Art Orientation – composition and drawing with pencil, charcoal and oil pastel, then outdoor investigation.  The art of collecting ideas.
	7pm	We make dinner, eat outside observing the sunset
Day 2	9am	Breakfast – Self-catering.
2	10am	Art Colour, Value and Harmony. These work together to create balance, mood, and visual unity in any artwork.
	1pm	Lunch – pranzo
3	2pm	Art Detail and Texture. They bring depth and realism and visual interest.
	4pm	A riposo – rest
	5pm	Aperitivo – cocktails
	6pm	We make dinner – we can share, or you can cook for yourself.
Day 3	06:30am	Drive to Cortona train station
	07:10am	Fast Train to Florence.  The normal trains throughout the day take 2 hours, but the fast one only 57 minutes.
	08:06	Leisurely stroll towards Cathedral of Santa Maria del Fiore and then to Via dei Castellani, close to Ponte Vecchio to meet our guide for the morning.
	09:30	Discover the most visited museums in Florence and two of the most visited in the world alongside a professional guide, admiring the most important works and appreciating the art of the Italian Renaissance, the Uffizi and the Academia. The guide will take you through the priority entrance into both galleries without having to wait in the long lines and explain the most important works of art.
	12:30pm	Now I’ll guide you to the famous Mercato Centrale – a food market where you can try some local street food and experience the best local cuisine.
		You are free to roam Florence for the afternoon.
	18:38	The fast train leaves for Cortona. Options are available if you want to stay longer.
Day 4	9am	Breakfast – colazione
4	10am	Art A discussion on Renaissance art and your experience in Florence.  Then an art class that is related.  Renaissance art, spanning the 14th to 17th centuries, emphasized realism, perspective, and human emotion, reflecting a renewed interest in classical Greek and Roman culture. Artists like Leonardo da Vinci and Michelangelo used innovation and skill to celebrate beauty, science, and the human experience
	2pm	Leave for cooking class, 10 km away.
	3pm	Cooking class at Villa Toscana near Cortona (5 hours).  Chef Dandy and Chef Otilia Real Italians! they will reveal the secrets of typical Tuscan home cooking!
	8pm	Return
Day 5		Your day off – consider Arezzo or laze around our house and garden.
Day 6	9am	Breakfast – colazione
5	10am	Art Art Appreciation exercises – by exploring cultural or historical contexts of art, you develop a personal connection and understanding of it.  Every art movement has symbolic and elements that make it unique.  We will explore these through practical observation and investigation.
	2pm	Lunch – pranzo
	3 pm	A Riposo
6	4pm	Art Watercolour essentials for Tuscany. They are techniques like washes, layering, and controlling water flow is key to creating vibrant, fluid, and expressive paintings.
	5pm	Dinner – cena
Day 7	9am	Breakfast
7	10am	Art Watercolour continued – using paints and linework. Combining watercolours and line work creates a dynamic balance between soft, flowing colours and sharp, defined details. This technique is perfect for adding structure, texture, and contrast to expressive watercolours washes
	1pm	Picnic
	3pm	A riposo
	7pm	Our Last Dinner – Il nostro ultimo pasto insieme
Day 8
	9am	Depart
Please note that the excursions were calculated at the time of planning this itinerary and is subject to change.

COST
Not sharing	R 39,500.00
Sharing:	R 33,000.00
Minivan (10-seater, 4 luggage) passenger airport and back including luggage and transport from lodging to Cortona, train stations and excursions, including fuel.	Available for first 4 reservations – R 3 500.00 Please note that you can rent a car for around R6000.00 for the 8 days or I can pick you up at the train station in Cortona.
Includes:	Accommodation for 8 nights in a private room with double bed and en-suit bathroom and full use of the self-catering facilities.
	7 Art Sessions including all materials.
	Return fast train ticket Cortona to Florence – excludes missed trains.
	Guided tour including priority entry to the Uffizi and Accademia galleries.
	Cooking class at Villa Cortona.
	Transport from train station to our lodging – a 9-seater, available for the first 7 or 8 bookings.  We will plan for everyone as far as possible.
	Small dinner 2 September.
Excludes:	Transport
	Food
	Airfare and Schengen Visa
	Meals at restaurants
	Insurance and breakages
	Curtailment and cancellations
	Entitlement…..