Wine & Jazz in Tuscany with Stella Cole
ITALY
November 1 - 6, 2026
Val d’Orcia
ITALY
This autumn, fall in love amidst the yellows and oranges of Tuscany with all things Italy and the voice of the acclaimed jazz vocalist Stella Cole. This is an invitation to those who love the magic that happens when artistry meets travel—a thoughtfully paced itinerary that balances daytime discovery with evening performances that capture the nostalgia of classic jazz, all against the rolling autumnal Tuscan landscape.
By day, wander historic streets and sun-drenched cafés at a relaxed, unhurried pace, soaking in the quiet charm of your surroundings. As the sun sets, the atmosphere shifts as we gather for warm, evocative concerts in beautiful settings, creating a unique week centered on connection, shared moments, and the timeless romance of Stella’s voice in the heart of the Italian countryside.
✦ Enjoy an intimate cooking class and jazz performance at a family-owned castle winery
✦ Tour an organic farm for an artisanal cheese tasting and a classic Chianti lunch
Highlights
✦ Savor farm-to-table meals and private concerts in the heart of the Tuscan hills
✦ Wander the winding streets of Pienza and Siena on guided historical tours
Stella Katherine Cole
The Artist
Stella Cole brings a cinematic magic to every room she enters. After our epic week in Cortona in the summer of ‘25, Stella returns to Italy to lend her velvet tones to some of Tuscany’s most beautiful spots. Her interpretations of jazz standards provide the heartbeat to our journey, turning every evening into an intimate, private performance.
The Experience
Harvest, Heritage & Harmony
This is Tuscany seen through the eyes of insiders — not rushed, but rich in taste, texture, and connection. It’s ideal for travelers who want to slow down, savour authentic places and food, and return home with a deeper understanding of Italian culture and hospitality.
Evening Jazz Soirees
We have secured exclusive access to private venues usually closed to the public. Picture Stella Cole performing an intimate concert within the walls of a historic Renaissance masterpiece in Pienza, or singing in an organic 'Pagoda' cellar where the music resonates not only with the audience but also with the vines themselves.
The Green Gold of Chianti
November in Italy is the month of the olive. During the week we’ll have the chance to head to an olive grove for an olive harvest experience where we’ll learn the ancestral art of pressing "green gold." And of course after a tasting of the young oil —a unique, peppery flavor — lunch will follow in the heart of the Chianti hills.
The Table & The Terroir
From a guided tour of the medieval towers of San Gimignano to a private cooking masterclass at a historic estate, every meal is a journey into mindful and immersive experiences. We dine at family-run cheese farms and Tuscany’s top-tier wineries, ensuring every bottle opened is as significant as the music played.
The Excursions
Explore the
Timeless Treasures of Tuscany
We’ll immerse ourselves in the rich history and breathtaking beauty of three iconic Tuscan towns. From medieval towers to Renaissance ideals, Montepulciano, San Gimignano, and Pienza each offer a unique journey through Italy’s cultural heritage.
Pienza
Uncover the charm of Pienza, known as the "ideal Renaissance town," crafted by Enea Silvio Piccolomini, later Pope Pius II. He transformed his humble birthplace, Corsignano, into a Utopian city reflecting the classical ideals and spirit of the Italian Renaissance.
San Gimignano
Discover the medieval charm of San Gimignano, famous for its iconic skyline of ancient towers. Wander its cobblestone streets, where history and beauty meet at every turn. With rich heritage, art, and culture, San Gimignano offers an unforgettable journey back in time.
Montepulciano
Wander Montepulciano’s narrow streets, where history, art, and tradition blend seamlessly. With its renowned wine and cultural treasures, Montepulciano offers a captivating experience that echoes through the ages.
The Accommodation
Private Boutique Stay
in the Heart of Val d’Orcia
Italian Country Charm
Authentically Tuscan, the villa has been beautifully refurbished while still maintaining its original character.
Glorious Grounds
The villa has a panoramic swimming pool and plenty of places to lounge and play. There are several sitting areas where you can read, chat or just take in the view.
Relaxing Spaces
A converted barn is now an extra living area and yoga studio with a view looking out onto the countryside and Montalcino in the distance.
Comfy Rooms
Each of the villa's rooms is spacious and comfortable. Some boast views across the valley while others face the thick trees in the back. Wake up to chirping birds and sleep to the soothing soft sounds of crickets and frogs.
Inclusions
Prices are per person and include:
Shared rooms starting at
£4200 per person
FAQs
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We recommend you fly into Florence as it's a small, easy airport to navigate and well connected to the city center. It's also where we're all going to meet in Piazza Santa Maria Novella on the first day of the retreat for private transfer to the villa. Alternatively, you can fly into Rome or Milan and take a train to Florence.
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Yes, absolutely. Write to us at duende@duenderetreats.com and we'll help with a bespoke itinerary suited to exactly what you're looking for.
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All are welcome! It's an itinerary that would be enjoyable for anyone who likes to eat, laugh, walk, cook, wine taste and explore. (Children not permitted.)
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Yes. When you register and pay your 30% nonrefundable deposit, you can opt into setting up a payment plan.
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Deposits are nonrefundable unless there's a waiting list and someone would like to take your spot. In the case we are able to sell your spot, you will be refunded your deposit, less £250 admin / transaction fees.
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The full itinerary will be sent to you about a month prior to departure. If you have specific questions regarding the excursions, please do reach out to us.
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