Discover a quieter, more intimate side of Tuscany where every garden path and villa doorway leads to beauty, history, and inspiration.
Designed for garden lovers, art and history enthusiasts, and all slow travelers, this is a rare opportunity to explore Tuscany through perhaps its most refined expressions of culture and nature.
We experience the region’s timeless elegance, from Renaissance towns and world-class gardens to scenic trails that link graceful villas and hilltop villages.
Led by Walk Leader Alessandro – an experienced horticulturist based in Florence – we gain expert insight into his passion for the spectacular gardens and landscapes of his native land.
Visit Siena, Pienza, San Quirico d’Orcia, and Radda in Chianti on a journey through the heart of Tuscany, where medieval charm, Renaissance beauty, and world-renowned wine culture come together.
Siena captivates with its Gothic architecture and iconic Piazza del Campo, while Pienza, a UNESCO World Heritage Site, stands as a model of Renaissance urban planning – and is famed for its pecorino cheese!
In the Chianti Classico region, we find a tranquil, authentic Tuscan experience with vineyard-draped hills, historic castles, and welcoming wineries offering tastings of some of Italy’s finest wines. The towns and villages here embody the rich cultural, historical, and culinary heritage that makes Tuscany so unforgettable.
Wander cypress-lined paths and olive groves, enjoy private visits to centuries-old estates including Villa La Foce, Castello di Celsa, and Villa di Geggiano, and explore garden masterpieces basking in that famous Tuscan light.
Along the way, enjoy authentic Tuscan hospitality with intimate wine tastings, family-style meals at local trattorias, and meet with the people who have preserved these special places for generations.
Our adventure begins in the enchanting medieval town of Siena, where cobbled streets and golden buildings set the mood for the days to come.
We settle into the ancient hilltop village of San Quirico d’Orcia, our home for the next two nights, where time slows down and the sunset glows over terracotta roofs.
Siena, Palazzo del Capitano
After a short morning drive, we step into Pienza, a jewel of Renaissance architecture and a UNESCO World Heritage Site shaped by the vision of Pope Pius II. A gentle walk then leads us down into the rolling fields of the Val d’Orcia, a dreamscape of golden hills, cypress-lined roads, and timeless beauty. This is a region so beautiful it’s as though we’ve stepped into a painting!
Our path brings us to Bagno Vignoni, a small village built around a steaming thermal spring that has bubbled since Roman times. We’ll enjoy lunch in a cozy local trattoria, soaking up the simple elegance of Tuscan cuisine.
In the afternoon, a short drive takes us to Villa La Foce, perched above the valley with breathtaking views of Mount Amiata. We’ll stroll through the romantic gardens, masterfully designed in the early 1900s by British architect Cecil Pinsent for the legendary Marchesa Iris Origo – a serene blend of Italian tradition and English formality.
Afterward, we return to the quiet charm of San Quirico.
Siena, Palazzo del Capitano
Today we journey west of Siena to the forested hills of the Montagnola Senese. A morning walk leads us through quiet paths to the private Castello di Celsa, a 14th-century castle still held by the noble Aldobrandini family. We explore its formal gardens and wander the former hunting grounds, with the towers of Siena rising in the distance like a mirage.
We reach a nearby agriturismo, where a hearty farm-to-table lunch awaits. In the afternoon, our path winds toward the Romitorio, a forest chapel once belonging to the Baroque Villa Cetinale. As we descend through its olive groves and woodland trails, we reconnect with our vehicle and head toward the Chianti countryside, where a new hotel and new flavors await.
Vescine, Borgo Vescine
This morning, we set off through the classic Chianti landscape, walking among vineyard rows and past hilltop hamlets, where time seems to stand still and the scent of wild herbs drifts on the breeze. Our destination is the fortified Castello di Monteriggioni, its intact medieval walls still encircling a living village straight out of a history book.
We’ll explore its winding alleys before sitting down for a leisurely lunch in the village. In the afternoon, we can choose our own adventure: continue walking a peaceful stretch of the ancient Via Francigena, once traveled by pilgrims on their way to Rome, or head back for a Tuscan cooking class, where we’ll prepare rustic recipes and share stories over flour-dusted countertops.
Vescine, Borgo Vescine
After a morning transfer northeast of Siena, we begin our walk at Ponte a Bozzone, weaving through wooded hills to the tranquil Certosa di Pontignano. This former Carthusian monastery, dating back to the 14th century, offers serene cloisters, restored gardens, and echoes of a monastic past-now lovingly maintained by the University of Siena.
A nearby trattoria welcomes us for lunch, and after another walk through vine-clad hills, we arrive at the elegant Villa di Geggiano. This 18th-century estate, still owned by the Bianchi Bandinelli family, opens its doors for a private tour through frescoed halls and sculpted gardens. We’ll end with a tasting of their handcrafted wines, savoring the essence of Chianti in every sip.
Later, we transfer to our hotel in Radda in Chianti, where the evening is yours to unwind.
Radda in Chianti, Relais Vignale
This morning begins with a visit to Badia a Coltibuono, a 1,000-year-old Benedictine abbey turned wine estate. We’ll explore its peaceful cloisters, ancient wine cellars, and fragrant gardens, followed by a guided tasting of their acclaimed wines and olive oils.
A scenic path leads us downhill to Gaiole in Chianti, where a relaxed lunch in a local trattoria awaits.
In the afternoon, we visit the grand Castello di Brolio, birthplace of the modern Chianti wine formula, created in 1872 by Barone Bettino Ricasoli. Still owned by the Ricasoli family, the castle’s stone ramparts and panoramic terraces offer unmatched views – and of course, we’ll conclude with a tasting of their renowned wines!
As the sun dips behind the hills, we return to Radda to prepare for a memorable farewell dinner, raising a glass to new friendships and those unforgettable Tuscan landscapes.
Radda in Chianti, Relais Vignale
After breakfast transfers will be arranged to Florence or Siena, where our onward journey continues.
