We love —
- Staying in two historic Tuscan hideaways where restored village buildings open onto quiet courtyards and rolling landscapes.
- Driving along panoramic roads with an included car hire between Pienza and San Quirico d’Orcia, where cypress-lined hills and golden fields unfold at every turn.
- Savouring a glass of Brunello in Montalcino, surrounded by vineyards and the soft, sunlit landscape of the region.
Customer reviews —
Welcome to Italy —
Set between the rolling hills of the Val d’Orcia and the quieter charm of the Valdera, this journey reveals an authentic Tuscany of medieval villages, cypress-lined roads and timeless landscapes. Along the way, stop at carefully selected wineries, where each tasting reflects the richness of the land and the Italian way of life.
Choose the length of your stay:
- 4 nights: 2 nights in Val d'Orcia and 2 nights in Valdera
- 6 nights: 3 nights in Val d'Orcia and 3 nights in Valdera
- 8 nights: 4 nights in Val d'Orcia and 4 nights in Valdera
Your suggested 6-night itinerary:
Day 1| Arrival in Val d’Orcia
Arrive in Rocca d’Orcia and feel immediately immersed in the beauty of Tuscany. Wander through its cobbled medieval streets, admire the Rocca di Tentennano overlooking the valley, and take in the golden light as it fades over the rolling hills. After check-in, stroll through the village, visit the church of San Simeone, and pause in the small square for an aperitivo with a view. End your day with a traditional Tuscan dinner, where pici al ragù or ribollita set the tone for the days ahead.
Night at Rocca d'Orcia Suites and Villas
Day 2| Val d’Orcia
Begin in Bagno Vignoni, where a medieval thermal pool steams quietly in the heart of the village. Continue to San Quirico d’Orcia and its peaceful Horti Leonini gardens, then on to Pienza, a Renaissance gem overlooking the valley. Taste the famous Pecorino cheese in a local cellar before heading back through one of Tuscany’s most iconic views: the Cappella di Vitaleta, glowing at sunset among cypress trees.
Night at Rocca d'Orcia Suites and Villas
Day 3| Val d’Orcia ⇄ Montalcino
Head to Montalcino, where the medieval fortress rises above endless vineyards of Sangiovese. Explore the town and enjoy a guided visit to a historic winery for a tasting of the world-renowned Brunello. In the afternoon, continue to the Abbazia di Sant’Antimo, a Romanesque abbey surrounded by olive groves. Return to your hotel for a private dinner overlooking the hills, closing the day in true Tuscan style.
Night at Rocca d'Orcia Suites and Villas
Day 4| Val d’Orcia → Valdera
Check out and set off towards the Valdera. On the way, stop in Siena and wander through the Piazza del Campo, enjoy a coffee near the Palazzo Pubblico, and step inside the Duomo to admire its extraordinary marble floor. Then continue towards the hills of Valdera. Arrive at Borgo di Colleoli, a medieval village transformed into an elegant resort surrounded by olive groves. Settle in and enjoy a relaxed evening aperitivo followed by dinner within the peaceful estate.
Night at Borgo di Colleoli Resort 5*
Day 5| Valdera ⇄ Volterra
Discover Volterra, a hilltop town rich in Etruscan heritage and dramatic landscapes. Explore the Guarnacci Museum, home to one of Italy’s most important Etruscan collections, then wander through artisan workshops dedicated to alabaster carving. End your visit in the Piazza dei Priori, one of Tuscany’s most perfectly preserved medieval squares.
Night at Borgo di Colleoli Resort 5*
Day 6| Valdera ⇄ Pisa & Lucca
Start your morning in Pisa at the Piazza dei Miracoli, home to the Leaning Tower, cathedral, baptistery and Camposanto. Continue to Lucca in the afternoon, where Renaissance walls encircle a refined historic centre. Cycle along the ramparts, climb the Torre Guinigi crowned with oak trees, and enjoy the city’s quiet, elegant atmosphere.
Night at Borgo di Colleoli Resort 5*
Day 7| Departure from Valdera
Enjoy a final day at leisure with an optional stop in San Gimignano, famous for its medieval towers and Vernaccia wine, or a tasting at the organic estate Usiglian del Vescovo near your accommodation. End your journey gently, with the flavours and landscapes of Tuscany still lingering.
The freedom to explore:
Discover our expertly curated self-guided tours, designed to offer the perfect balance of structure and flexibility. While our travel experts suggest itineraries to help you explore each destination in depth, you have the freedom to tailor activities and pace to suit your personal preferences. Rest assured, the carefully selected hotels will remain as listed, ensuring a comfortable and seamless experience throughout your journey.
Rocca d'Orcia Suites and Villas —
Set within the enchanting medieval village of Rocca d’Orcia, in the heart of the Val d’Orcia, Rocca d’Orcia Suites and Villas offers a refined retreat where history, nature and understated luxury meet. The property is spread throughout the village, with its suites and villas thoughtfully integrated into the historic surroundings, allowing guests to experience authentic Tuscan village life while enjoying modern comfort.
Surrounded by rolling hills, cypress-lined landscapes and panoramic viewpoints, the property invites guests to slow down and embrace the rhythm of the countryside. Its location provides an ideal base for exploring southern Tuscany, while maintaining a peaceful, intimate atmosphere in a setting defined by timeless beauty.
Please note that your hotels may be located inside or outside cities and towns. You may park your car inside or outside the hotels (subject to availability). Additional charges may apply on-site.
Your room —
Enjoy a stay in a Standard Room or Deluxe Room.
Standard Room (27 m²)
Deluxe Room (30 m²)
Your dining choices
Just for you:
- 10% discount at Rocca d’Orcia Grill
This is a bed and breakfast stay.
Dining at Rocca d’Orcia Suites and Villas is centred around the Rocca d’Orcia Grill, located within the village itself. The restaurant showcases traditional Tuscan cuisine, with a focus on seasonal, locally sourced ingredients and simple, authentic flavours. Guests can enjoy a selection of regional specialities alongside carefully chosen local wines, all served in a relaxed yet refined setting. The experience reflects the spirit of the Val d’Orcia, where gastronomy is deeply rooted in the land and its traditions.
Upgrade to half board
Choose to upgrade to half board at the next step of the booking process. Breakfast and your evening meal will be served in the main restaurant (drinks excluded, conditions apply.)
Your time
The hotel focuses on immersive, experience-led stays rooted in the local culture. Guests may enjoy the outdoor pool with sweeping views over the valley, as well as a wide range of curated activities including wine and food tours, cooking classes, truffle hunting and guided excursions.
Outdoor pursuits such as trekking, horseback riding and e-bike rental allow for exploration of the surrounding countryside, while wellness options include yoga sessions and massages.
Car hire: —
Discover Italy freely at your own pace with an included car hire for the entire duration of your stay.
Your included extras —
Wine tasting in Montalcino (18+)
Experience the essence of Tuscany with a guided wine tasting in Montalcino, where tradition, terroir and exceptional wines come together in an unforgettable sensory journey.
Your optional excursions —
Cheese tasting
Discover the authentic flavours of Tuscany with a tasting of traditional Pecorino di Pienza cheese, enjoyed in a local farm setting.
Tuscan cooking class
Join expert chefs for an immersive culinary experience and learn how to prepare traditional Tuscan dishes, from handmade pici pasta made with local grain flours to classic desserts such as cantucci and tiramisu. Take home the essence of Tuscan cuisine and recreate its flavours for family and friends.
Horse riding
Enjoy an authentic equestrian experience in partnership with nearby riding centres, offering programmes for all levels, from beginners to experienced riders. Choose between structured training sessions or guided excursions through the Tuscan countryside, from dressage and show jumping to scenic rides across the region.
Hot air balloon flight
Experience the Val d’Orcia from a breathtaking new perspective as you drift gently above its rolling hills, vineyards and medieval villages. A peaceful yet unforgettable journey offering panoramic views of one of Tuscany’s most iconic landscapes.
Borgo di Colleoli Resort —
Nestled on a gentle hilltop amid olive groves in the heart of Tuscany, Borgo di Colleoli Resort offers a refined stay between Pisa, Florence and Siena. This historic estate, dating back to the Middle Ages, has been carefully restored and transformed into an elegant retreat while preserving its original character.
The property unfolds across a traditional Tuscan borgo, centred around a noble villa and surrounded by former farm buildings now converted into guest accommodation. Its peaceful setting, overlooking rolling hills and unspoilt countryside, provides an ideal base for exploring the region’s cultural landmarks while enjoying a sense of seclusion and authenticity.
Please note that your hotels may be located inside or outside cities and towns. You may park your car inside or outside the hotels (subject to availability). Additional charges may apply on-site.
Your room —
Choose between a stay in a One Bedroom Apartment or a Two Bedroom Apartment.
One Bedroom Apartment
Two Bedroom Apartment
Your dining choices
Just for you:
- 1 x glass of wine with light snacks
This is a bed and breakfast stay.
Dining is centred around the Enoteca Leoli, located in the heart of the borgo’s main square. This welcoming space combines a relaxed atmosphere with a refined approach to traditional Tuscan cuisine. From generous breakfasts to light lunches and evening dining, the menu highlights seasonal produce, homemade pasta and locally sourced ingredients. A carefully curated selection of regional wines and cocktails complements the experience, allowing guests to enjoy the flavours of the region throughout the day. It is both a restaurant and a convivial gathering place, reflecting the spirit of Tuscan hospitality.
Upgrade to half board
Choose to upgrade to half board at the next step of the booking process. Breakfast and your evening meal will be served in the main restaurant (drinks excluded, conditions apply.)
Your time
The resort offers a range of leisure experiences designed to immerse guests in the Tuscan way of life. Unwind by one of the two panoramic outdoor swimming pools, set within the estate, and take in sweeping views of the surrounding countryside. Discover local traditions through curated activities such as wine tastings, cooking classes and truffle hunting.
Wander through the extensive grounds, dotted with woodland and olive groves, or take time to relax with a wellness treatment. The setting also invites you to explore nearby historic towns and cultural sites at your own pace.
Your excursions & activities —
Assistance at destination
Enjoy an included destination assistance service provided by our local partners trained to Voyage Privé standards. A dedicated contact person, available 24 hours a day (by phone or WhatsApp), will assist you throughout your stay with advice, reservations, or help in case of unforeseen circumstances. Travel with peace of mind.
Your journey to Italy —
Flights:
You will be able to choose your airline and flight times when you make your booking, in either Economy, Premium, or Business class, depending on the destination and carrier. This flight may include one or more stopovers. Please review your flight options carefully as departure and arrival airports may differ, in order to offer the best price.
Luggage information
Luggage, meals and other services on board may be subject to an additional fee on certain airlines. It is possible to view details of luggage allowances when you choose your flights at the next stage of the booking process. If luggage is not included with your flight, please go to the airline's website before your departure to purchase your luggage for an additional fee.
For domestic flights, airlines do not always offer the option of reserving luggage. In this case, you will need to pay for it at the airport counter.
You will receive all the information you need to check in for your flights after you have made your reservation.
Your destination —
Tuscany
Overflowing with artistic treasures, Tuscany is a timeless haven where ancient history meets rolling landscapes. From Etruscan origins to Roman marvels and Renaissance brilliance, this region is a journey through the ages. Beyond its celebrated cities, Tuscany invites you to explore serene vineyards, sun-dappled olive groves, and quaint villages that define its rustic charm.
Must-sees:
- Florence's Oltrarno District: Venture beyond the Arno River to discover artisan workshops, hidden gardens, and authentic trattorias.
- San Gimignano’s Towers: A medieval skyline framed by Tuscany’s picturesque countryside.
- Etruscan Legacy in Volterra: Wander ancient walls and explore artefacts in the Guarnacci Etruscan Museum.
Culinary culture:
Tuscany's culinary heritage is as rich as its landscapes. Indulge in seasonal Tuscan produce, from creamy pecorino cheeses to fragrant white truffles. Pair these delicacies with Chianti or Brunello di Montalcino wines from the region's renowned vineyards. Don’t miss rustic panzanella salads or ribollita, a hearty vegetable soup traditionally prepared with stale bread. For a sweeter note, try cantucci biscuits dipped in local Vin Santo.
Dive deeper:
Beyond Florence and Siena, Tuscany’s smaller towns reveal unique stories. In Pienza, you’ll find a Renaissance utopia shaped by Pope Pius II’s vision, while the Carrara marble quarries offer a glimpse into the artistry that crafted Michelangelo’s David. For a different perspective, take a cycling tour through the Val d’Orcia, a UNESCO World Heritage Site famed for its cinematic beauty.
Good to know:
The local currency is the euro (€), and Tuscany enjoys a mild Mediterranean climate, with spring and autumn being the ideal seasons to visit. Regional trains and buses connect towns efficiently, but renting a car offers the best flexibility for exploring the countryside’s hidden gems.