Adventure Collective
Discover Val d'Orcia: Explore Tuscany’s Timeless Landscape and Rich Heritage - Siena

Discover Val d'Orcia: Explore Tuscany’s Timeless Landscape and Rich Heritage

Califonmoderate

Difficulty

moderate

Duration

3–6 hours

Fitness Level

Suitable for moderate fitness; expect some hills and varied terrain that require endurance but no technical climbing

Overview

Experience Tuscany’s famed Val d'Orcia like never before—rolling hills, medieval towns, and world-class wines await on this immersive outdoor adventure. Discover why this UNESCO-listed valley is a must-visit for travelers seeking culture, scenery, and authentic Italian flavor.

Califon, New Jersey

Discover Val d'Orcia

8 hours • All Ages • Wine and Cheese tasting included • Private tour

Select participants and date

About This Adventure

Embark on an unforgettable 8-hour journey through the stunning Val d’Orcia, exploring charming villages and historic cellars. Savor the unique monk’s wine at Monteoliveto Abbey, indulge in Pienza’s renowned Pecorino cheese, and enjoy exquisite Brunello wine in Montalcino. Experience the essence of Tuscany in this captivating adventure.

Discover Val d’Orcia, Monteoliveto, Pienza, Montalcino. Wine and cheese tasting

Duration

8 hours

About

Take a drive by private vehicle to the unforgettable Val d’Orcia renowned for its outstanding natural beauty. You will delight a very special day visiting the real Tuscany between charming villages and cellars where local authentic wine is produced. We will pick you up at your hotel/structure around 8.00 am with a private van travelling all along the famous road of the Crete Senesi (Sienese clay) which resembles a lunar landscape characterized by the ochre-tinged soil. We will have a stop at the Abbey of Monteoliveto a unique monastic complex still marked by the schedule of the typical benedictine lifestyle, with rigid opening and closing hours and where you will taste the monk’s wine of their own making. In the morning we will visit Pienza the most well-known village of Val d’Orcia recognized as a UNESCO World Heritage Site there you will taste Pecorino di Pienza one of the best italian cheese with a long tradition. In the early afternoon departure to Montalcino with a stop along the way at an ancient castle to taste the excellent Brunello wine. Explore the medieval village of Montalcino rich in history and breathtaking views along its narrow streets. Return to the hotel in the evening.

Good to know

  • All Ages
  • A minimum of 2 participants is required
  • Pickup by minivan or car is available from your hotel or accommodation in Siena, San Gimignano, Certaldo, Monteriggioni o Montaione.
  • We are flexible with starting time, pickup points and duration of the tour. Reach out to our staff after the booking to share your needs and we will happy to accomodate them.

Adventure Tips

Bring layered clothing for temperature shifts

Val d'Orcia’s weather can shift from warm days to cooler evenings, so pack layers to stay comfortable all day.

Try local wines but drink responsibly

This region’s Brunello di Montalcino is world-renowned; enjoy tastings but remain hydrated and pace yourself on walks.

Use sturdy walking shoes

While many roads are paved, gravel paths and uneven terrain require good shoes for safe exploring.

Start hikes early to avoid afternoon crowds

Popular viewpoints and trails are less busy in mornings, letting you enjoy peace and better photos.

Local Insights

Wildlife

  • Red fox
  • European hoopoe

History

Val d'Orcia was officially designated a UNESCO World Heritage site in 2004 for its cultural landscape that shaped Renaissance urban and rural planning.

Conservation

Sustainable tourism practices are encouraged to preserve vineyards and fragile ecosystems; visitors should stay on marked trails to minimize impact.

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Frequently Asked Questions

Recommended Gear

Comfortable hiking shoes

Essential

Support and grip for varied Tuscan terrain including dirt and paved paths.

Light jacket or windbreaker

Essential

spring specific

Sunscreen and sunhat

Essential

Protect skin from strong Mediterranean sun during afternoon hikes.

summer specific

Camera or smartphone with good lens

Capture the stunning landscapes and historic architecture throughout your journey.