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Tuscany Val d’Orcia & Maremma Walk

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  • Location: Italy
  • Duration: 8 Days/7 Nights
  • Departing from: Orvieto
  • Tour finishes: Chiusi train station
  • Departures 2019: May 18, June 1, Sept. 14 & 28.
  • Price 2019: Euro €3,250 per person in double occupancy. Single supplement Euro €280. One guide accompanies departures of 2 - 8 people. Two guides accompany departures of 9 or more people.
  • Departures 2020: May 1 & 30, Sept. 12 & 26.
  • Price 2020: Euro €3,300 per person in double occupancy. Single supplement Euro €280. One guide accompanies departures of 2 - 8 people. Two guides accompany departures of 9 or more people.

This is a great trip for anyone who has already ‘done’  our classic Chianti -Tuscany tour, but wants more. This guided walking tour will take you to some lesser-frequented areas of the Val d’Orcia and the Maremma region of southern Tuscany.


Our Tuscan adventure gets away from the crowds of Florence and Siena and takes you southwest to the border with Umbria and Lazio, where you’ll find dramatic landscapes, a fascinating history, and delightfully authentic villages. You begin in the striking town of Orvieto, an ancient Etruscan fortress that dominates the valley below from a pedestal of volcanic rock. You’ll walk to the shores of Lake Bolsena, a crater lake created eons ago by a violent eruption, and hike through the famous Vie Cave, a network of trails carved directly into the volcanic tufa stone by the Etruscans. We stay two nights at a family-run farm near the beautiful village of Pitigliano, then transfer to the quintessential landscapes of the Val d’Orcia, a UNESCO World Heritage site renowned for its natural beauty and cultural importance. Stay two nights inside the medieval walls of Montepulciano, known for its heady Vino Nobile red wines. You’ll walk through verdant valleys dotted with olive groves, vineyards, and charming stone villages seemingly untouched by time. Enjoy your last two nights in the hilltop town of Montalcino, which produces its own world-famous wine, Brunello. This walking tour immerses you in Tuscany’s rich historical past while giving you plenty of time to enjoy the “dolce vita” with a frothy cappuccino or glass of wine as you people-watch in a sunlit square. And as always, we indulge your palate with wine tastings, fabulous dinners, and even a cooking lesson with a local family. It’s everything you always wanted from Tuscany, without the crowds! 
(Luggage is transferred by van. 1 night Orvieto, 2 nights Sorano, 2 nights Montepulciano, and 2 nights Montalcino. Tour finishes Chiusi train station.)

Tuscany Val d’Orcia & Maremma Walk itinerary

Day 1 – Saturday

Independent arrival in Orvieto, which is a direct one-hour train ride from Rome or two hours from Florence. Orvieto’s upper town is mostly pedestrian, and the streets are alive with boutiques, cafes, and trattorias that are frequented by the locals who live in the city’s medieval houses. Meet your Customwalks guide this afternoon and then get to know the city’s secrets with a guided visit of intriguing “underground” Orvieto, which makes a great introduction to the rich Etruscan history of the area. Dine tonight at a wonderful local trattoria.  Hotel and dinner included.

Day 2 – Sunday

Meet your guide(s) at 9 a.m. to transfer to the start of our walk. Follow paths and country roads as they gently meander towards the Lago di Bolsena, a dramatic volcanic crater lake. We stop in the charming town of Bolsena itself, once an important Roman outpost. Make your way down from the Rocca (castle) through narrow cobblestone streets to the lower town, where you enjoy a seafood lunch by the water. Afterwards, we transfer you to your home for the next 2 nights, the charming Locanda Pantanello, a family-run farm hotel. You’ll have time to rest up before meeting again for a special cooking lesson, where you will learn the secrets of local cuisine from our hosts. You enjoy the fruits of your labour as we dine on their terrace. Overnight at the Locanda Pantanello. The Walk: 8 km/5 mi., about 2 hrs. Hotel, breakfast, lunch, and dinner included.

Day 3 – Monday

A short morning transfer takes you to the enchanting village of Sovana, where you have free time to visit the medieval castle, Renaissance palazzi, and beautiful 12th century cathedral. Depart from there on foot and go back in time 3,000 years to enter the intriguing world of the Etruscans. You will see the tomb complexes of "Ildebrando" and "La Sirena" and then have a picnic lunch and wine tasting at a family-run winery, Sassotondo. We visit their wine cellar, which was carved directly into the local stone. A short transfer takes us to the sensational town of Pitigliano Retu, which rises up from the surrounding woodlands on a tufa plinth. Explore the medieval alleyways and enjoy the views before returning to your country hotel to relax by the pool. Dinner is another delicious meal made from ingredients and produce from the farm. Overnight Locanda Pantanello. The Walk: 12 km/7.5 mi. Hotel, breakfast, picnic lunch, and dinner included.

Day 4 – Tuesday

A one-hour transfer brings you to Bagno Vignoni, famous in both Roman and Renaissance times for its natural hot springs. Your walk begins here and takes you past ancient mills and bridges to the river before heading up again to the imposing castle of Rocca d'Orcia. The scenery hasn’t changed in centuries, so it’s easy to imagine what life must have been like amidst the drama of medieval intrigue. We eventually reach the castle itself and enter the grounds to have a picnic lunch with sweeping views across the valley to the Castle of Ripa D’Orcia, which stood guard above the river traffic below. You end the day in Montepulciano, which sits regally above the surrounding vineyards and olive groves. Your lodging for the next two nights is the Hotel Duomo (in superior rooms), a family run hotel with only a dozen rooms. It is perfectly situated inside Montepulciano’s Medieval walls on the pedestrian Piazza Grande. Tonight is a “free night” so you may dine where you like. Your guides will have lots of suggestions, from chic haute cuisine to cozy pizzerias and trattorias. The Walk: 11.5 km/7 mi., about 2hrs45 mins, 460 m/1,500 ft. elevation gain. Hotel, breakfast, and picnic lunch included. Dinner not included.

Day 5 – Wednesday

We have a more leisurely start this morning so you can enjoy a relaxed breakfast, perhaps even a second cappuccino in the sunny main square of Montepulciano before setting off for a beautiful loop walk departing from the historic Villa La Foce. Set amidst 3,500 acres of farmland, the 15th-century villa was bought in the 1920’s by Antonio and Iris Origo, who set about restoring the dilapidated villa and gardens. During WWII, at great personal risk, the family sheltered and hid escaped Allied P.O.W. and Italian Partisans from the Fascist Italians and the Nazi occupation. The front passed through the estate, and the villa was held as a defensive position by German paratroopers. Iris Origo’s fascinating first-hand account of this time can be read in “War in the Val D’Orcia.”  After lunch at their wonderful restaurant, you’ll have a guided visit of the gardens, which are considered to be among the finest in Italy. Return to Montepulciano for some free time, and then dine at the Osteria Acquacheta, a local shrine to the famous Tuscan steak, Bistecca alla Fiorentina. The Walk: 8 km/5 mi., 250 m/800 ft. elevation gain. Hotel, breakfast, lunch and dinner included.

Day 6 – Thursday

Depart from Montepulciano on foot this morning, past the late Renaissance church of San Biagio, and make your way to the hilltop farm “Podere Il Casale” for lunch, where you’ll taste one of their most important products: pecorino or sheep's milk cheese. Continue on to Pienza, silhouetted against the sky with its proud cathedral watching over the Orcia valley. It’s another UNESCO World Heritage site thanks to the efforts of Pope Pius II, who was born there. After becoming pope in 1458 he transformed his humble village into a Papal retreat and a centre of Renaissance culture, architecture, and town planning. Admire the perfect harmony of his vision and then refresh your palate with a delicious gelato at an artisanal ice cream maker just off the main square. A short transfer takes you to the hilltop village of Montalcino, which offers breathtaking views over a patchwork of vineyards, olive groves, and golden wheat fields. Your hotel is perched on the hillside just outside the 14th-century archway that leads into the historic centre. After a dip in the panoramic pool, head to the hotel garden to relax and enjoy the uninterrupted views over the Tuscan countryside. Dine tonight in a wonderful small restaurant that features ancient beams, terracotta floors, and a wine list that has a vast array of superb vintages of Brunello di Montalcino. The Walk: 10 km/6 mi., 236 m/774 ft. elevation gain. Hotel, breakfast, lunch, and dinner included.

Day 7 – Friday

Stroll through the cobblestone streets of the Montalcino this morning and head past the castle into the vineyards and woods beyond. Become a modern-day pilgrim as you make your way on foot to the beautiful 12th-century abbey of Sant’Antimo. We stop en route at the Villa a Tolli, which produces Brunello wines, for a light lunch accompanied by a restrained (still more walking to do after lunch!) tasting of their wines. We then descend a narrow path through woods and olive groves to Sant'Antimo, an outstanding example of Romanesque architecture set in a serene setting below enormous olive trees. Enter inside the hushed silence for a guided tour of this still-functioning Benedictine Abbey. Return by van to Montalcino, where you have free time to explore the gems and secrets of the old town. Or you may want to continue your wine education with another (optional) tasting of Brunello at the Enoteca del Consorzio located inside the historic castle. Our final night’s dinner is at Boccon di Vino, a fabulous restaurant with stunning views. The Walk: 12.6 km/7.8 mi., 250 m/800 ft. elevation gain. Hotel, breakfast, lunch and dinner included.

Day 8 – Saturday

After breakfast we provide a van transfer to arrive at the Chiusi train station for trains to Rome, Florence, and beyond. We depart Montalcino at 9 a.m. in time for the 10:54 train to Rome (arr. Roma Termini train station at 12:48) and for the 10:58 train to Florence (arr. at the Florence S.M.N. train station at 12:48). Breakfast and transfer included.

The walks in Tuscany

The walks 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.

Useful Links

Iris Origo and Villa la Foce: basic information about this amazing woman and her beautiful villa
The Etruscans: everything you always wanted to know but were afraid to ask!
Siena Tourist Information: informative site from the Province of Siena, including links to areas like the Val d’Orcia, the Crete Senesi, etc.
Brunello di Montalcino: official site of the Consortium of Brunello producers
UNESCO World Heritage Sites: Italy has more sites in the list than any other country!

Activity Level 2 + = Easy to Moderate Plus:
In general: This is an Easy to Moderate tour for fit hikers, and a little challenging but do-able for not-so-fit hikers.
Terrain: Flat to gently rolling terrain but with some rocky, rugged terrain. May have some short, relatively steep climbs and descents, but nothing longer than 30 minutes of sustained ascents or descents. The walks are shorter in distance than those found on a 3 rated tour. 
Actual walking time: Between 2-4 hours per day, mostly in the morning but sometimes also in the afternoon.
Distances: Usually between 7 and 10 kms/4.5 and 6 miles. Max distance is 12 kms/7 miles.
Surfaces: Trails consisting of mostly compact earth, gravelly earth, and sometimes dirt-gravel roads and on occasion rocky and uneven trails.
Footing: Good, but on occasion you have to pay attention to where and how you place your feet. Proper hiking shoes with thick soles with good treads are required. Sport sandals, running shoes and tennis shoes are not adequate.
Specifics: The most challenging walk is on day 3 since it has a lot of up and down. On day 4 there is a gradual but sustained uphill of 1.5 kms. On day 5 there is also a sustained but gradual uphill on a dirt road for 2 kms, which is about a half an hour of walking.
Hiking Poles: Not required, but if you habitually use hiking poles then you will find them helpful.  
Compared to the Cinque Terre: This tour is significantly easier than the hikes in the Cinque Terre.
Other: This tour is appropriate for fit first time “hikers” who enjoy walking and who have good balance and are coordinated. 
Easy to Moderate Plus Tours: in this category are all of our boat–based tours in Turkey, Croatia, and Greece if you decide to do all of the walks on offer. On these trips, we usually do a walk in the morning, return to the boat for a swim and then lunch, then cruise, then sometimes drop off for another late afternoon hike, which you could skip and just relax on the boat. Your guides of course can advise you of the difficulty level and the terrain and footing of each walk. Other Easy to Moderate Plus tours are: Tuscany Val d’Orcia & Maremma Walk and Provence Walk

Trip Cost Includes: Accommodations for seven nights, (1 night Orvieto, 2 nights Sorano, 2 nights Montepulciano, and 2 nights Montalcino); 7 breakfasts, 7 lunches 7 dinners; bilingual Customwalks guide(s) to accompany the tour and lead you on the walks; all van transfers and luggage transfers; all visits as per itinerary (Orvieto underground visit, Etruscan tombs and necropoli, winery visit, wine tasting, cooking lesson, pick-up from Orvieto and transfer to Chiusi train station at the end of the tour. 

Booking: e-mail us at info@customwalks.com to receive a booking contract (or use the 'Contact Us' link at the top of this page), or click on the 'Book Now' button to the right.

Insurance: We highly recommend the purchase of Trip Insurance. We recommend “Travel Guard” to our North American clients, just click on the logo below.  Australian, New Zealander, and British travelers, please consult your insurance brokers.

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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 Saturday morning with a one hour transfer to the Chiusi train station for rail connections around noon. Please see the itinerary.

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.

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Reviews
5
by Mtn_hiker from US
Posted Jun 19, 2018

This Tuscany trip was great. We hiked across kilometers of hills covered in wheat fields, olive orchards, and vineyards, through Etruscan towns and cities. The view of the landscapes could have been from gallery paintings. We took a cooking class and visited castles, family farms and wineries. The history of the area was an additional benefit. We visited cities with Etruscan tombs, ate at restaurants with Etruscan ruins and caverns in the basement. The same facial features found in Etruscan sculptures can be seen in people living in the hill top cities today. This part of Tuscany felt open and expansive. The hikes were fantastic. The guide knowledgeable and fun. The wine was exceptional. The food and gelato were amazing. If you are looking for a reason to visit or revisit the Tuscan/Etruscan part of Italy, this hike is it. You can tell that the people who worked to put this tour together love Tuscany and want to show it off.

5
by Jaye Gregory from Melbourne Australia
Posted Feb 18, 2015

Wonderful walking tour and very accommodating. I felt I did not want to walk one afternoon and Brett found me a lovely village to explore and I met the group later. It was a mix of beautiful scenery, lovely Italian Hill Top Towns, great lunches and dinners and a lovely group of fellow travellers all masterfully organised by our guides.

5
by Peter Todd from Australia
Posted Feb 04, 2015

Great tour. We were burning 10000 cals per day but unfortunately taking in 15000. What with 5 course lunches and 8 course dinners, not to mention 5 gallons of wine per day. Accomodation was varied and excellent.



This Tuscany trip was great. We hiked across kilometers of hills covered in wheat fields, olive orchards, and vineyards, through Etruscan towns and cities. The view of the landscapes could have been from gallery paintings. We took a cooking class and visited castles, family farms and wineries. The history of the area was an additional benefit. We visited cities with Etruscan tombs, ate at restaurants with Etruscan ruins and caverns in the basement. The same facial features found in Etruscan sculptures can be seen in people living in the hill top cities today. This part of Tuscany felt open and expansive. The hikes were fantastic. The guide knowledgeable and fun. The wine was exceptional. The food and gelato were amazing. If you are looking for a reason to visit or revisit the Tuscan/Etruscan part of Italy, this hike is it. You can tell that the people who worked to put this tour together love Tuscany and want to show it off.
by Mtn_hiker from US

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