Hiking tours


Tuscany Val d’Orcia & Maremma HikingTour

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Tuscany Val d’Orcia & Maremma HikingTour Write a review

  • Location: Italy
  • Duration: 8 Days/7 Nights
  • Departing from: Orvieto, Sunday Day 1
  • Tour finishes: Chiusi train station
  • Departures 2025: April 27, May 11, Sept 7, Oct 5, plus private departures.
  • Price 2025: Euro €3,850 per person in double occupancy. Single supplement Euro €490. One guide accompanies departures of 2 - 8 people, two guides for 9 or more.

This is a great tour for anyone who has already done our classic Chianti – Tuscany itinerary but wants more. This guided hiking tour will take you to some lesser-frequented areas of the Val d’Orcia and the Maremma region of southern Tuscany 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 hike 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 in the medieval hilltop town of Montalcino, known for its heady Brunello red wines and your last two nights in the unique Renaissance village of Pienza. As always, we indulge your palate with wine tastings, fabulous dinners, and even a cooking lesson with a local family.
(Luggage is transferred by van. 1 night Orvieto, 2 nights near Pitigliano, 2 nights Montalcino, and 2 nights Pienza. Tour finishes at the Chiusi train station.)

Tuscany Val d'Orcia and Maremma HikingTour Includes:

  • Accommodation: 7 nights in 3 & 4-star hotels and B&Bs (1 night Orvieto, 2 nights each Pitigliano, Montalcino, and Pienza)
  • Meals: 7 breakfasts, 6 lunches, 6 dinners
  • Special events: Cooking lesson with family; tasting at Brunello producer; entrance and guided visit of Villa La Foce (if possible); farm lunch at Podere Il Casale
  • Transport: All private van/bus transfers as noted in the itinerary from pick-up in Orvieto and final transfer to Chiusi train station
  • Active days: 6 days of guided hiking
  • Guides: At least 1 bilingual Customwalks guide accompanies departures of 2 - 8 people; 2 guides accompany departures of 9 or more people
  • Max group size: Tours are capped at 14 people

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.

Tuscany Val d’Orcia & Maremma HikingTour itinerary Request full itinerary

Day 1 Arrive Orvieto

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 guide(s) and the rest of the group at 6:30 tonight for drinks followed by dinner at a local trattoria. Overnight Orvieto. Hotel and dinner included.

Day 2

Morning transfer to the start of our hike. 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, transfer to your home for the next 2 nights, the charming Locanda Pantanello (or similar), a family-run farm hotel. You’ll have time to rest before a cooking lesson where you will learn the secrets of local cuisine from our hosts. Enjoy the fruits of your labour as we dine on their terrace. Overnight at the Locanda Pantanello in Pitigliano. The Hike: 8 km (5 mi), about 2 hrs. Hotel, breakfast, lunch, and dinner included.

Day 3

A short morning transfer takes you to the enchanting village of Sovana, where you visit the medieval castle, Renaissance palazzi, and beautiful 12th century cathedral before departing on foot and travel back in time as you hike along the 3,000-year-old Vie delle Cave, which were carved from the tufa rock by the Etruscans. You will see the intriguing Etruscany tomb complexes of "Ildebrando" and "La Sirena" and then have a picnic lunch and wine tasting at a family-run winery. We visit their wine cellar, which is carved directly into the local stone. A short transfer takes you to the sensational town of Pitigliano, 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 Pitigliano. The Hike: 12 km (7.5 mi) Hotel, breakfast, picnic lunch, and dinner included.

Day 4

A 90-minute transfer brings you to Bagno Vignoni, famous in both Roman and Renaissance times for its hot springs. Your hike 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. We eventually reach the castle itself and enter the grounds to enjoy the sweeping views that medieval soldiers once commanded hundreds of years ago. We have a picnic lunch in a small piazza and then transfer to the hilltop village of Montalcino. Your hotel, the Vecchia Oliviera, is perched on the hillside just outside the 14th-century archway that leads into the historic centre. After a dip in the pool, relax in the garden and take in the uninterrupted view over a patchwork of vineyards, olive groves, and golden wheat fields that lay far below you. 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. Overnight Montalcino. The Hike: 11.5 km (7 mi), about 2hr45 mins, 460 m (1,500 ft) elevation gain. Hotel, breakfast, picnic lunch, and dinner included.

Day 5

Our hike leaves directly from the hotel. Stroll through the cobblestone streets of Montalcino, pass the castle and head into the vineyards and woods beyond the village. Become a modern-day pilgrim as you make your way on foot to the beautiful 12th-century abbey of Sant’Antimo, an outstanding example of Romanesque architecture set in a serene setting amongst ancient olive trees. We have lunch at a local trattoria in the village of Castelnuovo Dell'Abate followed by a very special wine tasting at Azienda Uccelliera, one of Italy’s best producers of Brunello di Montalcino. You will taste different vintages directly from the barrel and learn about and taste the importance of “terroir” in determining the taste and style of wine in your glass. Return by van to Montalcino. We have a "free night" tonight so you are free to dine where you like. Overnight Montalcino. The Hike: 12.6 km (7.8 mi), 250 m (800 ft) elevation gain. Hotel, breakfast and lunch included. Dinner not included.

Day 6

A short transfer after breakfast brings us to the small Renaissance town of 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. We hike out of Pienza, beneath its defensive walls and into the strikingly beautiful countryside. Our destination is the Cappella della Madonna di Vitaleta, a perfect chapel set amongst golden wheat fields and flanked by two sentinel cypress trees. Nearby, a renovated farm house is now an improbable and discreet osteria where we enjoy a mid-morning break. We loop back to Pienza and then have a short transfer to the hilltop farm “Podere Il Casale” for an unforgettable lunch. Continue on to Montepulciano this afternoon where you'll have time to explore the town or just relax with a gelato or glass of wine before returning to our hotel, the Relais Il Chiostro. A former Franciscan Convent dating back to the 13th century it is now a four-star hotel with elegant rooms and a panoramic terrace overlooking the dramatic landscape below. Overnight Pienza. The Hike: 10 km (6 mi), 236 m (774 ft) elevation gain. Hotel, breakfast, lunch, and dinner included.

Day 7

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 before setting off for a beautiful loop hike departing from the historic Villa La Foce. Set amidst 3,500 acres of farmland, the 15th-century villa was bought in the 1920s 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 trattoria, you’ll have a guided visit of the gardens*, which are considered to be among the finest in Italy (*if possible: the gardens are frequently closed for private events). Return to Pienza for some free time, and then dine at one of the town’s most beloved trattorias. Overnight Pienza. The Walk: 8 km (5 mi), 250 m (800 ft) elevation gain. Hotel, breakfast, lunch and dinner included.

Day 8

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

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.

Activity Level 2 + out of 5Easy to Moderate Plus:
In general: This is an easy to moderate tour for fit hikers, and will be a little challenging but do-able for less 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. The hikes are shorter in distance than those on a 3-rated tour. 
Actual hiking time: Between 2 - 4 hours per day, mostly in the morning but sometimes also in the afternoon
Distances: Usually 7 - 10 km (4.5 - 6 mi). Max distance is 12 km (7 mi).
Surfaces: Trails consist mainly of compact earth and/or gravel and sometimes gravel roads, with frequent 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 hike 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 hiking.
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 hiking and who have good balance
Easy to Moderate Plus Tours: in this category are all of our boat–based tours in Turkey, Croatia, and Greece. On these trips, we usually do a hike in the morning, return to the boat for a swim and then lunch, then cruise for a few hours to our next destination, 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 hike. Other Easy to Moderate Plus tours are: Tuscany Val d’Orcia & Maremma Hike and Provence Hike.
As a point of reference, what is a 1 out of 5 Activity rating? A 1 out of 5 rated tour is a tour without any hiking. Hikes would be in towns, cities, and villages, and the countryside hikes would be on paved, or gravel/dirt roads, and occasionally on some packed earth trails. Elevation gain and loss would be negligible.
As a point of reference, what is a 5 out of 5 Activity rating? A 5 out of 5 rated tour is a tour that would be physically challenging and technically difficult even for very fit and experienced hikers. The hikes would have steep ascents and descents on narrow, exposed trails with challenging footing, such as on scree fields, or through rock falls and boulders. Distances would be up to 25 km/16 miles per day and feature ascents of over 1,000 m/3,200 feet in a day. A 5 out of 5 tour would also mean that you would be carrying a heavier-than-normal pack. None of our tours are rated 5 out 5. Our most challenging tours are 4.5 out of 5, and they are the Dolomites Alta Via (because of some exposed trail that requires some technical expertise) and our Republic of Georgia tour which has some long hikes with over 1,000 meters of elevation gain.

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.

5 out of 5
Ratings based on 10 Verified Reviews

Average ratings
Quality of itinerary
Food quality & variety
Value for money
Right amount of activity
Overall satisfaction

by Michele C
Posted Oct 31, 2022

My husband and I just finished a wonderful Customwalks trip - the "Tuscany, Orcia, Maremma" tour with Manu and Dennis. This was a 5-star trip in every category. Dennis and Manu were friendly, funny and had wonderful attitudes. They knew a lot about the area and the history, were flexible and had amazing patience. The food and all the hotels were awesome. The hiking was perfect - some challenging days and some just fun days. I can't recommend this company enough and we can't wait to go again!

by JonathanS
Posted Oct 25, 2022

Great food and beautiful walks; the whole trip was very well paced and planned. The guides were amazing, always well informed and fun the whole time. Overall, a great experience.

by Alex K
Posted Oct 24, 2022

I absolutely loved my experience. Our guides Manu and Dennis were absolutely lovely and very knowledgeable. The entire tour was very well planned out, eat meal and hotel gave a unique glimpse into the area's history and culture. I will definitely be returning soon!

by Bill S
Posted Oct 24, 2022

We love seeing countries by foot, interacting with guides, fellow walkers and locals. The history of the region remains visible in the old Roman roads, the layers of building in the hilltop cities and, even, in the centuries old wine cellars. Our guides, Manu and Dennis, were fantastic: enthusiastic, knowledgeable and engaging. We would definitely do another tour with either of them. The walks were varied and not terribly challenging, with only a couple sections of significant vertical change. Our accommodations were all outstanding and staying for a couple of nights in most places gave time to explore the area. This was our third Italian trip with Customwalks (four if you count one they did for REI.) and we've never been disappointed.

by Will R
Posted Apr 24, 2020

A walk through primo wine country! What's not to like? Combine the wine tasting with a small group of like-minded travelers, fun and informative guides (Manu and Manu), spectacular scenery, fascinating history, charming towns, and food to die for -- and you have a most memorable week. I'm regularly making the home made pasta and tomato sauce we learned to prepare at our cooking class in the farmhouse where we stayed for two nights. This trip offers memories for a lifetime -- or at least until enjoy another Customwalks trip.

by Linda and John
Posted Oct 02, 2019

We had a wonderful walking holiday in Tuscany and were well looked after by Emanuela and Manuela...…..a wealth of knowledge, energy and enthusiasm. Around every turn was a beautiful vista and when we came to rest, there was delicious and carefully selected food and wine. We are already thinking about a Custom Walks tour for next year.

by Jayne from Berkeley
Posted Sep 29, 2019

This was my 5th tour with CustomWalks and it was magnificent. As always, the days were perfectly planned and the restaurants, hotels, and agriturismos were well vetted. The guides, who are invariably knowledgeable, fun and enthusiastic, take you on hikes that offer both history (in this case, Etruscan trails, tombs, and more) and incredible vistas. Plus, CustomWalks always seems to slip in at least one unique cultural experience. On this tour, the matron of a family-run farm stood at the head of a long table and taught 13 of us how to make pasta (Pici and Fettuccini). It turned out to be an incredibly fun (and hilarious) experience and, afterward we ate our pasta for dinner, which by the way was fantastic! The Val d’Orcia and Maremma tour was fantastic! I’ll be back for more!

by Mtn_hiker
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.

by Jaye Gregory
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.

by Peter Todd
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.

If you have any questions or specific requests about any of our tours, we’re here to help. You can fill in the form below, send us an email, or call us and we’ll get back to you as soon as possible.

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My husband and I just finished a wonderful Customwalks trip - the "Tuscany, Orcia, Maremma" tour with Manu and Dennis. This was a 5-star trip in every category. Dennis and Manu were friendly, funny and had wonderful attitudes. They knew a lot about the area and the history, were flexible and had amazing patience. The food and all the hotels were awesome. The hiking was perfect - some challenging days and some just fun days. I can't recommend this company enough and we can't wait to go again!
by Michele C

Great food and beautiful walks; the whole trip was very well paced and planned. The guides were amazing, always well informed and fun the whole time. Overall, a great experience.
by JonathanS

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