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From those famous cypress-lined country roads to medieval towns steeped in centuries of history—welcome to Val d’Orcia, a Tuscan pastoral dream. On this dream tour, we’ll hike from town to town through some of the world’s most stunning rural landscapes. And this is no exaggeration. Recognized as a UNESCO World Heritage Site, Val d’Orcia epitomizes the ideals of Renaissance agricultural landscapes. Picture countryside so breathtaking that it not only inspired artworks, but that it’s celebrated as a masterpiece in its own right! And when we blend in Tuscan wines, local cuisine, and remarkable architectural heritage, we can confidently say there’s hardly another destination where hiking and exploring Italian culture intertwine so seamlessly.

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  • Landscape as a work of art

    Explore gorgeous Tuscan countryside, meticulously cultivated over centuries to embody the aesthetic ideals of the Renaissance

  • Exquisite local cuisine and wines

    Get a chance to try local dishes and delicacies, paired with world-class wines

  • All the logistics taken care of

    Enjoy quality accommodation with breakfast, daily guided hikes and tours, and luggage transfers between hotels


Set out on a week-long adventure through the picturesque landscapes of Val d'Orcia on our hiking tour. Explore charming medieval towns, hike through rolling hills draped in patchwork quilt farmland, and marvel at historic landmarks along the way. With experienced local guides, quality accommodations, breakfasts, and luggage transfers provided, immerse yourself in the beauty of Tuscany. From Florence to Montalcino, Sant'Antimo, Pienza, Bagno Vignoni, and Rocca d'Orcia, this journey promises an unforgettable blend of nature, culture, cuisine, and active relaxation.

  • Begin your Tuscan adventure with an arrival in Florence, a city renowned for its rich history, stunning architecture, and vibrant culture. As you settle into your accommodations, soak in the atmosphere of this iconic city, known as the birthplace of the Renaissance. Explore the cobblestone streets, visit world-class museums such as the Uffizi Gallery and the Accademia Gallery, home to Michelangelo’s masterpiece, David, and indulge in irresistible Italian cuisine at local trattorias. With its breathtaking beauty and timeless charm, Florence promises to be an unforgettable starting point for your journey through Tuscany.

    Vedute of Florence.
  • Our day starts with a train ride from Florence to Torrenieri, a scenic ride that offers glimpses of the picturesque Tuscan countryside. From Torrenieri, our adventure continues with a delightful trek to Montalcino, a charming hilltop town famous for its exquisite wines, particularly the renowned Brunello di Montalcino. Wander through the narrow streets lined with medieval buildings, visit historic wineries for tastings, and savor the panoramic views of the surrounding vineyards and rolling hills. Montalcino’s timeless beauty and old-world charm make it the perfect destination to kick-start your hiking expedition in Tuscany.

    Meals: Breakfast
    Hiking: 10 km (6.2 miles)
    Elevation: +500 m (+1640 ft) / -150 m (-492 ft)

    Vedute of the Tuscan hilltop town of Montalcino, Val d'Orcia.
  • Today, we’ll Immerse ourselves in the tranquility of the Tuscan countryside as we go on a scenic hike from Montalcino to the enchanting Sant’Antimo church and back. Nestled amidst rolling hills and vineyards, the ancient abbey of Sant’Antimo is a true gem of Romanesque architecture and a peaceful retreat for contemplation. Take in the serene atmosphere and admire the timeless beauty of this spiritual haven. The picturesque landscapes and cultural heritage of Sant’Antimo promise another memorable hiking experience in the heart of Tuscany.

    Meals: Breakfast
    Hiking: 17 km (10.6 miles)
    Elevation: +/- 400 m (+/-1312 ft)

    Church interior of the Romanesque church of Sant’Atimo, Val d’Orcia, Tuscany.
  • Today’s adventure takes us from Montalcino to the charming town of San Quirico d’Orcia. We’ll explore the historic streets, admire the architecture, and soak in the authentic Tuscan atmosphere. Meander through the quaint alleys, visit the Collegiate Church of San Quirico and the Horti Leonini, a Renaissance garden, and marvel at the panoramic views of the Val d’Orcia. The timeless beauty and cultural heritage of San Quirico d’Orcia make it a must-visit destination on our Tuscan itinerary.

    Meals: Breakfast
    Hiking: 14 km (8.7 miles)
    Elevation: +250 m (+820 ft) / -400 m (-1312 ft)

    Hiker in the countryside surrounding the town of San Quirico d’Orcia.
  • After breakfast, we’ll set out from San Quirico d’Orcia on a picturesque hike to Pienza and back. Discover the UNESCO World Heritage-listed town of Pienza, renowned for its Renaissance architecture and panoramic views of the Val d’Orcia. Explore the charming streets lined with historic buildings, visit the Piazza Pio II, and sample the local pecorino cheese, a specialty of the region.

    Meals: Breakfast
    Hiking: 16 km (9.9 miles)
    Elevation: +/-500 m (+/-1640 ft)

    Aerial view of the Tuscan town of Pienza and surrounding patchwork fields, at dusk.
  • Today, we’ll embark on yet another delightful hike from San Quirico d’Orcia to the thermal village of Bagno Vignoni. Once there, we’ll take a relaxing break and rejuvenate your senses with a dip in the soothing thermal waters before returning to your accommodations. Explore the charming village center, admire the ancient thermal baths, and stroll along the scenic trails surrounding Bagno Vignoni.

    Meals: Breakfast
    Hiking: 8 km (5 miles)
    Elevation: +150 m (+492 ft) / -250 m (-820 ft)

    Bagno Vignoni, a thermal water town in Val d’Orcia.
  • Today, we’ll explore the scenic wonders around Bagno Vignoni as you hike to Rocca d’Orcia and back. Marvel at the rugged beauty of the landscape and capture breathtaking views of the surrounding valleys and hilltop villages. Discover the medieval fortress of Rocca d’Orcia, perched atop a hill overlooking the Val d’Orcia, and immerse yourself in the rich history and natural splendor of the region.

    Meals: Breakfast
    Hiking: 12 km (7.5 miles)
    Elevation: +/-500 m (+/-1640 ft)

    Landscapes surrounding Rocca d’Orcia, a fort and a nearby town in Val d’Orcia, Tuscany.
  • As our unforgettable journey through Tuscany draws to a close, bid farewell to Bagno Vignoni and embark on your return journey to Florence. Reflect on the memories made and the breathtaking landscapes explored during your exhilarating Val d’Orcia hiking adventure in the heart of Italy’s stunning countryside. Arrive in Florence refreshed and rejuvenated, ready to continue your exploration of this timeless city or depart for home or your next destination!

    Meals: Breakfast

    Ponte Vecchio in Florence.
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Meet your guides

Guido is an expert mountaineer and founder of Freemotion Trekking Italia. In addition to having covered thousands of kilometers everywhere in the Dolomites, Guido has a deep knowledge of them. Beyond the Dolomites, he leads tours in the Lake Garda area, Tuscany, Amalfi Coast, Cinque Terre and Sicily. In his company, you can learn many interesting things about the "most beautiful mountains in the world" and other gorgeous places in Italy.
Freemotion Trekking Italia
Freemotion Trekking Italia
Freemotion Trekking Italia
Freemotion Trekking Italia is a passionate team of Mountain and Hiking Guides based in the heart of the Dolomites. Beyond the rugged beauty of the Dolomites, we offer immersive hiking tours in some of Italy's most stunning locations, including the Amalfi Coast, Lake Garda, Cinque Terre, Tuscany, and Sicily. With years of experience guiding people of all ages and backgrounds, safety is our top priority, but our commitment goes beyond that. We believe in enriching experiences that delve into the local culture and natural wonders of each destination. Our excursions are more than just walks; they're opportunities to connect with nature, learn about local traditions, and create lasting memories. From the moment you join us, expect a warm welcome and leave with a heartfelt hug, as we share our love for hiking and the beauty of Italy with you.

Things to know

  • What you get on this adventure:

      • An experienced, local hiking guide and a local tourist guide with extensive knowledge of the area
      • Week long Val d’Orcia hiking tour
      • Accommodation in 3 or 4-star hotels and B&Bs for the duration of the tour (6 nights), based on double occupancy
      • Breakfasts
      • Train/bus ticket to reach/leave the starting/ending point of the tour
      • Luggage transfers between hotels

    What’s not included:

      • Transportation to Florence
      • Accommodation in Florence before the Val d’Orcia tour (Day 0)
      • Meals other than breakfast (your guide will organize dinners at high-quality local restaurants with incredible wines, but you’ll be able to go elsewhere)
      • Guide gratuities — optional
      • Travel and medical insurance — recommended
  • To participate in our guided Val d’Orcia hiking tour in Tuscany, you should have a moderate level of fitness and be comfortable with full-day hikes. You should be able to maintain a stable and safe pace, as well as have no fear of heights. The tour involves covering between 5 and 10 miles (8-17 km) each day, with hiking durations of approximately 4 to 6 hours, sometimes over hilly terrain. While there may be some challenging sections along the way, you’ll always have a guide by your side to set the appropriate pace, ensure regular breaks, and ensure the safety and enjoyment of everyone in the group.

  • Here’s a list of the equipment you need to bring:

      • Day pack large enough to carry all the items you may need during the day (around a 25-40L bag)
      • Hiking poles — optional
      • Water bottle or hydration bladder (2L capacity)
      • Lightweight hiking boots or shoes with good ankle support
      • Comfortable hiking clothes, both short-sleeved and long-sleeved, to last you for a week
      • Midlayer or fleece
      • Waterproof lightweight rain jacket
      • Casual clothes for when you’re not hiking
      • Swimsuit
      • Sunhat
      • Toiletries (sunscreen, hand sanitizer, bug spray, etc.)
      • Sunglasses
      • Camera — optional (but recommended)

    Bring comfortable clothes appropriate for the season. We suggest checking the forecast and adjusting your list accordingly. Layers are best and don’t wear jeans.

  • Group sizes and pricing

      • For this group adventure, the maximum client-to-guide ratio is 12:1. You will either be led by a hiking or a tourist guide, depending on the activity.
      • It takes a minimum of 6 people for this tour to operate.

    This hiking tour in Val d’Orcia can be arranged for private and for larger groups. Contact us to make arrangements.

    Min. age requirements

      • If you are older than 18, you’re good to go.
      • Minors younger than 18 may be permitted to join the hike on a case-by-case basis, but must be in the presence of a parent or legal guardian.

    If your group has hikers under the age of 18, contact us prior to booking to make arrangements.

  • To get to Florence, most people fly into Florence Amerigo Vespucci Airport, which is connected to the city center with a regular tram line.

    Once you and your guide agree on the details of your itinerary, your guide will suggest the best time and place to meet in Florence, usually at the train station in the moring of Day 1.

  • We highly recommend that you cover all your bases with both emergency medical and travel insurance.

    With medical insurance, if you have an accident or medical emergency on or off the trails, you’ll avoid paying out of pocket for costly expenses. This covers everything from hospital treatments to emergency air transportation and more. Travel insurance covers canceled flights, natural disasters and other scenarios that may interrupt your travel plans.

    We also expect you to respect local regulations and take measures to protect yourselves, your guides, and the communities you’re traveling to. If you need assistance selecting the right insurance for your group, let us know and we will be happy to help!

  • A 30% deposit to secure your place is due upon booking. The deposit is fully refundable in the first 48 hours. The remaining amount is paid 3 months (90 days) prior to departure. Once the trip is confirmed by the guide, the cancellation policy stated below applies.

      • If Client cancels the Booking anytime prior to ninety (90) calendar days in advance of the trip contemplated by the booking, Client is entitled to a full refund, minus the deposit.
      • After that deadline, Client is not entitled to any refund.
      • Booking fees are non-refundable.
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