Tuscany Val d’Orcia & Maremma Hike

This morning, a short transfer brings us to the start of our walk. We follow scenic paths and country roads as they gently wind their way toward Lago di Bolsena, a stunning volcanic crater lake with a dramatic shoreline.Our route leads us to the lakeside and the charming town of Bolsena, once a vital Roman outpost. We pass the imposing Rocca (castle) as we stroll down the narrow cobblestone streets to the lower town, where a leisurely seafood lunch awaits by the water. After lunch, we transfer to your home for the next two nights: the delightful Locanda Pantanello, a welcoming family-run “Agriturismo”. You'll have time to relax before a casual cooking lesson with our hosts, where you'll learn the secrets of traditional local cuisine. This evening, we savor the fruits of our labor, dining together on the terrace, surrounded by the tranquil countryside. Overnight at the Locanda Pantanello in Pitigliano. The Hike: 8 km (5 mi), about 2 hrs. Hotel, breakfast, lunch, and dinner included.

This morning, a short transfer brings you to the enchanting village of Sovana, where history comes to life as you explore its medieval castle, Renaissance palazzi, and beautiful 12th-century cathedral. From here, we set off on foot, traveling back in time along the Vie delle Cave, an extraordinary network of 3,000-year-old sunken pathways carved into the tufa rock by the Etruscans. Along the way, we visit the fascinating Etruscan tomb complexes of Ildebrando and La Sirena, silent remnants of an ancient civilization. Our journey continues to a family-run winery, where we enjoy a picnic lunch paired with a wine tasting. Here, the experience is made even more special by a visit to their wine cellar, carved directly into the local stone. A short transfer then takes us to the breathtaking town of Pitigliano, dramatically perched on a tufa cliff above the surrounding woodlands. You'll have time to wander its medieval alleyways and take in the stunning views before returning to your countryside hotel for a well-earned rest by the pool. Tonight’s dinner is another delicious farm-to-table feast, made with fresh ingredients sourced directly from the estate. Overnight Pitigliano. The Hike: 12 km (7.5 mi) Hotel, breakfast, picnic lunch, and dinner included.

This morning, we set off on an hour’s drive to Sant’Angelo in Colle, a charming hilltop village where we pause for a coffee and a WC break before beginning our hike. Stepping onto the trail, you’ll feel like a modern-day pilgrim as we make our way on foot to the stunning 12th-century Abbey of Sant’Antimo, a masterpiece of Romanesque architecture set in a tranquil landscape of ancient olive trees. Lunch awaits in the village of Castelnuovo dell’Abate, where we dine at a cozy trattoria before heading to a truly special wine tasting at Azienda  Podere Le Ripi, one of Italy’s finest producers of Brunello di Montalcino. Here, you’ll taste different vintages and experience firsthand how terroir shapes the character and complexity of the wine in your glass. A short 20-minute transfer brings us to your hotel, Vecchia Oliviera. Perched on the hillside just outside the 14th-century gateway to Montalcino’s historic center, this modest but charming retreat boasts a pool, a garden, and sweeping views over a picturesque patchwork of vineyards, olive groves, and golden wheat fields stretching far below. Tonight’s dinner is at a truly special spot: Ristorante Boccon di Vino, where exquisite cuisine meets unforgettable views. The Hike: 7 km (4.6 mi) in the morning, 250 m (800 ft) elevation gain. Duration 2 hrs. Hike to the winery after lunch 3.2 kms (2 mi) and 120 m (380 ft) elevation gain. Duration 1 hr. Hotel, breakfast, picnic lunch, and dinner included.

Today, we take you to Bagno Vignoni, a village renowned since Roman and Renaissance times for its soothing hot springs. Our hike begins here, leading us past ancient mills and stone bridges as we descend to the river before climbing again toward the imposing Rocca d’Orcia. Reaching the castle, we step into its historic grounds, where medieval soldiers once stood watch over the sweeping landscapes below. After taking in the breathtaking views, we enjoy lunch at a charming trattoria in the village before continuing our loop hike back to Bagno Vignoni. Here, we take a well-earned pause to soak our feet in the warm thermal waters—a perfect way to unwind before returning to Montalcino. This evening is a free night dinner so can choose when and where you would like to dine. Your guides will have lots of suggestions for you.  The Hike: 11.5 km (7 mi), about 2hr 45 mins, 460 m (1,500 ft) elevation gain. Hotel, breakfast and lunch included. Dinner not included. 

After breakfast, a short transfer brings us to Palazzo Maissani, a 16th-century fortified villa, where we begin our hike. Our route takes us through woodlands and open fields before descending panoramically toward the medieval walled village of Monticchiello. Lunch is in a charming trattoria tucked beneath ancient vaulted ceilings, offering a perfect setting to savor local flavors. Afterward, there's time to wander Monticchiello’s cobbled streets in search of Via San Luigi 13, where, in the 1700s, a disgruntled homeowner carved an unflattering likeness of his neighbor—the man he accused of betraying him to the taxman. The stone-carved face remains, a centuries-old act of revenge meant to shame a lowdown spy! This afternoon, you’ll have free time to explore the beautiful hilltop town of Montepulciano before checking in at Relais Il Chiostro in Pienza. Once a 13th-century Franciscan convent, this elegant four-star hotel boasts refined rooms and a panoramic terrace with breathtaking views of the dramatic landscape below. Dinner is in the village tonight. Overnight in Pienza. The Hike: 10 km (6 mi), 236 m (774 ft) elevation gain. Hotel, breakfast, lunch, and dinner included.

We have a leisurely start this morning, giving you time to enjoy a relaxed breakfast—perhaps even a second cappuccino in the sunny main square—before setting off on a stunning loop walk directly from the hotel. Our route takes us out of Pienza, beneath its ancient defensive walls, and into the strikingly beautiful countryside. Our destination is the Cappella della Madonna di Vitaleta, a picture-perfect chapel set amidst golden wheat fields, flanked by two stately cypress trees. Nearby, a beautifully restored farmhouse now houses an improbable yet discreet osteria, where we pause for a mid-morning break. We then loop back to Pienza before a short transfer to the hilltop village of Montefollonico, where lunch awaits at Relais La Chiusa. Seated beneath a trellis of grapevines in the cobbled courtyard of this former 18th-century olive mill, we savor a delicious meal in a truly timeless setting. After lunch, there's time to meander through Montefollonico’s ancient alleyways before returning to Pienza for some free time. A UNESCO World Heritage site, Pienza owes its elegant transformation to Pope Pius II, who was born here. Upon becoming pope in 1458, he reimagined his humble village as a refined papal retreat and a Renaissance masterpiece of architecture and town planning. You’ll have time to explore its charming streets or simply unwind with a gelato or a glass of wine. This evening, we dine at Ristorante La Terrazza della Val d’Orcia, where the superb cuisine is matched only by the breathtaking view. Overnight Pienza. The Hike: 8 km (5 mi), 250 m (800 ft) elevation gain. Hotel, breakfast, lunch and dinner included.

We offer one group transfer after breakfast this morning to the Chiusi train station in time for 10 a.m. departures to Rome, Florence, and beyond. Breakfast and transfer included.

Please note: Some details of the itinerary may change according to the departure date of your tour. Whenever we run a tour we make new discoveries. Sometimes they are good discoveries, like a wonderful new trattoria, and sometimes they are bad, like a trail has been washed away. The result is that we sometimes change our itinerary to improve it by adding new wonderful elements to the tour or by removing something that does not work anymore. Rest assured, our goal is to always provide you with the best possible experience. We will advise you of any changes to the original itinerary prior to departure.  

The hikes in Tuscany cover a variety of terrain, from trail to dirt road, with many rolling hills to climb or descend. We have designed the trip so that there is always some free time in the late afternoon so you can relax, read, or enjoy the towns where we stay. Breakfast is included every day, and dinners reflect the excellent traditional food of the region. Daily distance between 8 and 16 kms.

Getting There: Orvieto is located half-way between Florence and Rome, and is easily reached by train from both cities. Travel time from Rome is an hour by train, and from Florence it is just under two hours.

Air: The closest airport is either Florence or Rome. You could also fly into Pisa if you find a good deal on a low-cost flight. For a complete list of Italian airports and a selection of low-cost airlines, see our "Transport Info" page.

Rail: Orvieto is only 1 hour from Rome by train and around 2 hrs from Florence (some trains depart only from the Campo di Marte station – on the north side of town, a 10-minute taxi or train ride from the main station — so be sure to check which is the departure station!). See the Trenitalia website (in English) at this link. For alternative high-speed rail travel, see the Italo website.
For complete information on using the Italian train system, see our blog post.

Getting Away at the End of the Trip: the trip ends after breakfast on Sunday morning with a transfer to the Chiusi train station for 10 a.m. departures.

If you book a trip with us, you will receive detailed information about how to get to the start of your trip, or feel free to e-mail us with any specific travel questions.