Carefully curated selection of activities and excursions are designed to highlight the region’s landscape and culture.



The Tuscan countryside resembles an immense living canvas, a painting brimming with nature, wildlife, history and unique activities. Rosewood Castiglion del Bosco provides the ideal base for exploring this fascinating region. The 800-year-old estate is situated on the ancient Via Francigena, a route travelled by merchants and pilgrims, in the heart of the UNESCO-protected Val d’Orcia. A meandering, cypress-lined road leads to the Borgo, the historic heart of the state’s bygone farming community. Located on a hilltop, overlooking patchwork fields that stretch out below towards Montalcino, the Borgo was the center of the estate’s activities for hundreds of years. Dominated by the ruins of the medieval castle that gives the estate its name, it is a place brimming with memories.

Further afield, Tuscany is a fascinating, multi-layered landscape that invites discovery. Guests can immerse themselves in Italian gastronomy, wine itineraries, active leisure pursuits, historical sightseeing and the timeless traditions of local artisans, craftsmen and farmers. Local guides and exclusive access make the experiences richer when exploring the region’s unique way of life.


Castiglion del Bosco Golf Club

The estate’s beautiful 18-hole golf course was designed by legendary British Open winner Tom Weiskopf. Set in a UNESCO World Heritage Site, it offers an unparalleled playing experience at Italy's only private golf club.


Osteria La Canonica Cooking School

At the estate’s cooking school, guests learn how to transform fresh local ingredients into delicious, authentic Tuscan and Italian dishes using traditional cooking skills. The engaging chef-led classes are kept deliberately small to ensure personal attention and hands-on involvement. Classes begin in the organic kitchen garden before moving indoors to the interactive atmosphere of the kitchen. 

Lessons are offered daily from 10:00 a.m. to noon and 4:00 to 6:00 p.m. All classes, except the Pizza Experience, include a tasting meal and glass of wine. Preferred meal times are requested and accommodated based on availability. 

For more information about the schedule or to arrange private lessons, please contact Guest Relations.

Explore the Val d'Orcia

The Val d’Orcia region of Tuscany is a UNESCO World Heritage Site famous for its stunning landscapes, cultural heritage and excellent red wines. With its gentle, carefully cultivated hills, dotted with cypress trees, red poppies and yellow sunflowers, and its small picturesque medieval towns, it is a landscape which has been depicted and celebrated in works of art over the centuries. 

This exceptional tour provides an ideal introduction to the region. It includes visits to some of the Tuscany’s most iconic locations and to several enchanting traditional Tuscan villages.

Biking through Tuscany

The gently rolling Tuscan countryside is ideally suited to exploration by bike. Fully immersed in the beautiful natural environment, the sensorial experience is immensely rewarding, engaging and personal. In the Val d’Orcia, a UNESCO World Heritage Site, one can explore Montalcino’s sundappled vineyards, discover charming farmhouses and tiny medieval villages, and visit the historic Abbey of Sant’Antimo near Rosewood Castiglion del Bosco. 

An itinerary can include a stop at the spectacular Crete Seines and Monte Oliveto Abbey, follow the ancient pilgrimage road, Via Francigena, through the heart of the valley, or trace a portion of the famous L’Eroica bike racetrack.


Osteria La Canonica Cooking School

The former priest’s house in the heart of the Borgo is home to the estate’s La Canonica Cooking School. Small, chef-led classes offer hands-on experience in Tuscan culinary traditions inspired by freshly harvested produce from the adjacent organic garden which contains over 180 varieties of vegetables and herbs. The atmosphere is interactive and the two-hour class concludes with a meal that the participants and chef have prepared together. Course topics include pasta and sauces, pizza, a three-course meal and vegetarian dishes. 

Olive Oil Mill Visit

Tuscany is one of the world’s preeminent olive oil producers. A visit to the region presents a superb opportunity to learn all about EVO (extra virgin olive oil). Pay a visit to one of the most renowned olive mills in the region, recognized for its quality and professionalism. Learn how to identify an exceptional oil and sample a few of the varieties. While exploring this modern olive mill is fascinating year round, mid-October to mid-December is the optimal time to witness the molitura.

Truffle Hunting

Take part in a memorable truffle hunt accompanied by local experts and their highly trained dogs. A taste of mouth-watering truffles is enjoyed at the close of the hunt. The two-hour outing takes place 30 minutes from the estate and is offered throughout the year except in May.

Organic Farm and Pecorino Experience

Experience the wonders of a traditional family-run organic farm and cheese factory. Uncover the secrets of cheese production during a cheese-making demonstration, sample the delicious products and enjoy a peaceful lunch in a charming tavern. The farm is located 50 minutes from the estate. 

The World of Bees

Discover the world of honey and bees by visiting a local beekeeper. Learn everything about the incredible and indispensable nectar produced in the area of Montalcino which is recognized internationally as the “City of Honey.”


Explore Bolgheri by Helicopter

Bolgheri is world-famous for its Super Tuscan wines. This exclusive luxury tour by helicopter and car departs from the estate for Tenuta San Guido (Sassicaia) at 10:00 a.m. After a breathtaking flight over the beautiful Val d’Orcia, a tasting of Sassicaia is followed by car transfer to the Ristorante La Pineta, a Michelin-starred seafood restaurant in Marina di Bibbona. 

Returning to Tenuta San Guido at 3:30 p.m., guests fly to Tenuta dell’Ornellaia for an exceptional wine tasting experience. The adventure comes to a close at 6:00 p.m. on return to Rosewood Castiglion del Bosco. The helicopter flight is confirmed the night before, based on weather conditions.

Montepulciano: Vino Novile, Art and EVO

A historical town located between the Val d’Orcia and Val di Chiana, Montepulciano fascinates visitors with its rich history, beauty, Renaissance palaces and renowned Nobile di Montepulciano wines. Accompanied by an expert guide exceptionally well versed in enogastronomy, guests set out on a half-day tour of the town and its historic winery located within the city walls. A visit to an additional winery concludes the tour. 

For a well-rounded exploration of the region’s specialties, guests can continue on a full-day adventure. A visit to a renowned olive mill to learn all about Tuscany’s extraordinary EVO (extra virgin olive oil) follows lunch at a charming local restaurant.

Unexpected Siena, Il Palio and its contrade

Experience the wonders of nearby Siena on a fascinating half-day excursion led by an experienced local guide. This tour provides participants with exclusive access to the private and historical contrade (district) of Il Palio, site of the wordrenowned horse race held twice a year in the Piazza del Campo. Afterwards, guests embrace the city’s rich cultural heritage with a visit to one of the Siena’s oldest bakeries and a relaxing walk through the heart of the historical town.

Val d'Orcia: The Hidden Gems

Delve deeper into the mystique and history of the Val d’Orcia. For travelers who are already familiar with Tuscany, this fascinating tour presents an opportunity to explore some of the region’s hidden treasures including the spectacular Crete Senesi and the unforgettable Abbey of Monte Oliveto Maggiore.


Landscape Painting Class

Capture the stunning natural surroundings of Rosewood Castiglion del Bosco on canvas while enjoying a lovely day outdoors in the sundappled vineyards or in the enchanting gardens of your private villa. Gathered around a table stocked with artist-quality materials, participants learn the basic techniques of watercolor while composing a typical Tuscan landscape. Led by an artist-instructor with many years of experience, the lesson can be adapted to suit all ages and abilities.


For archery enthusiasts or those interested in learning this classic sport, an archery field and all the necessary equipment are available. Under the direction of an experienced teacher, guests can learn or practice this sophisticated interest.




Throughout the year, cultural festivals, historic celebrations, wine events and sporting engagements mark the changing seasons in Tuscany. Rosewood Castiglion del Bosco is brilliantly positioned to allow guests to join in the rich and varied local and regional events.