Tuscany Gourmet Walking Escape 6D5N (from Chianti to Val d'Orcia), Fully Guided

TWO HIKING OPTIONS:
Level 1, Approx. 8km (3 miles), Elevation gain: 152m (500 ft)
Level 2, Approx. 10km (5 miles), Elevation gain: 274m (900 ft)

Benvenuti in Italia! Begin your journey with the breathtaking landscapes of Tuscany, where rolling hills and timeless charm await. Discover the enchanting medieval village of Castellina, nestled in the heart of Chianti Classico. Perched atop a hill, Castellina offers sweeping views of verdant valleys and the heroic vineyards that define the Tuscan countryside. Once a fortified Florentine outpost until the fall of Siena in 1555, this historic hamlet exudes a unique soul that comes alive in its winding alleys, charming piazzas, and centuries-old olive groves, all framed by dry stone walls now recognized as a UNESCO World Heritage Site.

Take a leisurely stroll along Castellina’s scenic pathways, forest trails, and iconic strade bianche (white gravel roads), soaking in the region’s timeless beauty. Along the way, stop at a family-run farmhouse-turned-villa for an exclusive olive oil tasting led by a local expert. Then, indulge in a delightful alfresco pranzo (lunch) buffet, savoring the flavors of Tuscany under the open sky.

After lunch, enjoy a serene descent through the woods and the meticulously cultivated vineyards, traversing forested paths and gravel roads. This quintessential Tuscan landscape feels like a masterpiece come to life—a place so stunning, it might seem too perfect to be real.

Settle into the enchanting Hotel Villa Campomaggio Resort & Spa, our home for the next two nights, nestled perfectly to showcase the breathtaking views of the Chianti Valley. Take some time to explore the hotel's serene grounds, relax by the swimming pool, or savor a tasting of the estate’s own Chianti Classico wine. For an added touch of indulgence, treat yourself to a rejuvenating massage this evening (spa treatments are not included in the trip price, and advance reservations are highly recommended). As the sun sets, raise a glass of prosecco to an unforgettable week ahead before enjoying a delicious dinner at the hotel.

THREE HIKING OPTIONS:
Level 1, Approx. 5.5km (3.4 miles), Elevation gain: 183m (500ft)
Level 2, Approx. 7.1km (4.4 miles), Elevation gain: 374m (900 ft)
Level 3, Approx. 11km (6.8 miles), Elevation gain: 366m (1200 ft)

Other Activities: Tuscan Cooking Class 2 Hours

This morning, after a delightful breakfast, soak in the stunning views of the Ricasoli fortresses nestled in the surrounding hills as we take a shuttle to Gaiole to kick off today’s adventure. A gentle climb through serene woodlands leads us to a scenic ridgeline, offering sweeping views of Radda in the distance, as we make our way toward the beautifully preserved hamlet of Vertine. From there, the trail descends below the village, winding through quaint rural communities and endless rows of meticulously tended vineyards. Our journey culminates at a beloved agriturismo—a charming working farm and countryside retreat—where we’ll enjoy a leisurely lunch featuring local flavors.

This afternoon brings the perfect opportunity to slow down and immerse yourself in the enchanting village of Radda in Chianti. Whether you choose to browse for unique souvenirs or simply wander its charming streets, it’s a delightful experience. Alternatively, you may opt to return to the hotel to unwind by the pool or indulge in some rejuvenation at the spa.

This evening, we gather for a hands-on cooking class hosted by our local amici (friends), who are deeply passionate about their cuisine and heritage. Welcomed into the heart of their home—the cucina (kitchen)—we’ll learn the art of authentic Italian cooking, discovering the secrets of daily culinary traditions. The night promises unforgettable moments filled with delicious food, fine local wine, and warm camaraderie. Afterward, we retreat to the hotel for a well-earned rest, ready to embrace tomorrow’s culinary adventures.

TWO HIKING OPTIONS:
Level 1, Approx. 5.3km (3.3 miles), Elevation gain: 122m (400 ft)
Level 2, Approx. 7km (4.3 miles), Elevation gain: 213m (700 ft)

Other Activities: Truffle Hunting & Wine tasting

We begin the day with a shuttle ride to the 14th-century Abbey of Monte Oliveto Maggiore, a serene monastery still home to Benedictine monks. Founded in 1313 by Sienese merchants seeking refuge from the distractions of city life, the abbey offers a fascinating glimpse into history. Stroll through its peaceful grounds and visit the cloisters, where you’ll find some of Europe’s finest Signorelli frescoes—Renaissance masterpieces celebrated for their lifelike figures and remarkable use of perspective.

From there, we set off on a scenic walk along ridges framed by breathtaking landscapes, making our way toward San Giovanni d’Asso. Along the route, don’t miss the chance to pause at Chiusure, where you’ll enjoy panoramic views of the abbey and the iconic crete senesi—the chalky hills of Siena. Upon reaching San Giovanni d’Asso, we’ll delve into the world of truffles with a local tartufaio (truffle hunter), learning about these prized delicacies while savoring a decadent, truffle-inspired lunch.

After lunch, we hop into the van for a short drive to Bagno Vignoni, a charming town renowned for its ancient thermal baths, which date back to Etruscan times. Legend has it that both the Medici family and Saint Catherine of Siena once sought the healing properties of these waters. While here, treat yourself to a refreshing gelato and soak in the tranquil atmosphere of this historic gem.

For the next three nights, we’ll stay at Hotel La Posta & Thermal Spa*, which looks out onto the ancient Roman baths. Take some time this afternoon to relax at the hotel spa if you’re feeling indulgent. In the evening, we’ll head to a nearby agriturismo in the rolling countryside for a wine tasting and a delightful dinner, the perfect end to a day rich in culture, flavor, and history.

* For some departures, the Night 3 hotel is at Palazzo Leopoldo. Located in the heart of the Chianti region, this boutique 14th-century manor house features spacious guest rooms with original frescoes.

THREE HIKING OPTIONS:
Level 1, Approx. 4km (2.5 miles), Elevation gain: 153m (500ft)
Level 2, Approx. 6.4km (4 miles), Elevation gain: 274m (900 ft)
Level 3, Approx. 15km (9 miles), Elevation gain: 548m (1800 ft)

Other Actvities: saffron-inspired cooking demonstration

After bidding goodbye to Chianti, head to another legendary Italian wine area: Montalcino, the birthplace of the renowned Brunello varietal. Following a brief shuttle ride, our adventure begins at the Abbey of Sant'Antimo, a stunning example of Tuscan Romanesque architecture. Take a moment to explore the grounds and soak in the rich history that lingers in the air.

From the abbey, we set off on foot toward the charming village of Castelnuovo dell'Abate, strolling along the Val d’Orcia’s picturesque "strada bianca" (white roads). Along the way, pause to admire the breathtaking views of rolling vineyards and the abbey nestled in the distance.

Our first destination is the renowned Mastrojanni winery, where we delve into the fascinating history of saffron cultivation and its economic significance in the Val d’Orcia over the centuries. Here, the winery’s chef treats us to a demonstration of saffron-inspired dishes, perfectly paired with Brunello di Montalcino wine for an unforgettable gastronomic experience.

After lunch, we continue our hike through one of Val d’Orcia’s most secluded and enchanting corners. Along the trail, marvel at the striking views of the Ripa d’Orcia castle, Castiglione d’Orcia, the winding Orcia River, and the quaint hamlet of Vignoni Alto.

This evening, relax and enjoy dinner on your own in the picturesque town of Bagno Vignoni. Buon appetito!

THREE HIKING OPTIONS:
Level 1, Approx. 5km (3 miles), Elevation gain: 153m (500ft)
Level 2, Approx. 8km (5 miles), Elevation gain: 213m (700 ft)
Level 3, Approx. 15km (9 miles), Elevation gain: 427m (1400 ft)

After enjoying breakfast at the hotel, we set off on foot toward the picturesque village of San Quirico d'Orcia, following the gravel paths of the historic Via Francigena, an ancient pilgrimage route. Take some time to explore this enchanting walled town or pause for an espresso at a local café.

From there, we embark on a scenic walk through the breathtaking Val d'Orcia, a UNESCO World Heritage site. The gently rolling paths offer ever-changing views: vibrant green hills in spring, golden fields with scattered hay bales in early autumn, and freshly plowed earth in late fall. Our journey continues along quiet farm roads lined with cypress trees and fertile landscapes, leading us to a gourmet trattoria owned by a local friend. Here, we savor a delicious lunch and enjoy a demonstration of traditional desserts.

Afterward, unwind on the trattoria’s terrazza, soaking in sweeping views of Pienza in the distance.

For the afternoon, choose to shuttle back to Bagno Vignoni for some relaxation, or extend your adventure with a walk across the rolling hills to the magical town of Pienza. This charming Renaissance village was transformed in the 15th century by Florentine architect Bernardo Rossellino, commissioned by Pope Pius II to create a model town embodying Renaissance ideals. Stroll through the main square to admire two architectural masterpieces: Palazzo Piccolomini and the elegant duomo.

Once you’ve finished exploring, return to Bagno Vignoni to rest and rejuvenate. In the evening, we come together to celebrate our incredible Tuscan adventure with a farewell aperitivo and dinner at the hotel’s restaurant.

Level 1, Approx. 4.4km (2.7 miles), Elevation gain: 213m (700ft)

Spend a relaxing morning at the hotel or take one last opportunity to the fortified hamlet of Vignoni Alto to soak in our last views of the Val D'Orcia. Bid a farewell to your culinary adventure in Tuscany and board a private coach for Florence, leaving inspired and relaxed for your onward journey.

NOTE: This itinerary is provided as an example only – prevailing conditions and local arrangements may cause variation.