“The Apennines are a paradise for anyone who likes to be active in nature and the outdoors on holiday.”
Myrtle claus, this is italy
An Apennine Mountains Hiking Adventure in Tuscany is a journey into one of Italy’s most intriguing landscapes, where rugged peaks meet rolling hills, and ancient traditions still shape everyday life. The Apennines are softer and greener than the Alps, with chestnut and beech forests, meadows dotted with wildflowers, and ridge lines that open to sweeping views over the provinces of both Tuscany and Emilia-Romagna. Trails often follow centuries-old shepherds’ paths, Roman roads, or sections of the historic Via di Francesco (Way of St. Francis), making the walks as cultural as they are scenic.
Along our route, we pass through stone-built villages, Romanesque churches, and fortified monasteries that speak to Tuscany’s medieval past. The pace of life is slow, and we indulge that by stopping for trail lunches made with the crusty Florentine schiacciata, visiting a village brewery, having lunch at a country butcher, and learning to make cheese at a farm enclosed in one of the national preserves.
One of the most unique aspects of this tour is that the region is relatively unvisited by non-Italian tourists. On our recent tour there, after leaving our starting city of Florence and prior to arriving to our ending city of Sansepolcro, we saw a total of two groups of foreign visitors: an Australian couple and a group of French students. Not an American accent the entire trip.
About Apennine Mountains Hiking
Walking through Italy is an incredible way to see the country. We are not in a hurry, which allows us to stop whenever we see something interesting: a country farm selling fresh produce, a field of wildflowers, or a fellow hiker who has a story to tell. We learn from our friend and local guide Giovanni about everything Italian – wine and cuisine, history and culture, and so much more. We enjoy being disconnected from the world on the one hand and yet intimately connected to it on the other.
We hike 7.5 to 10.5 miles each day in the Apennine Mountains in Tuscany for six days in a row. We use transfers to avoid most of the larger uphills in the region, keeping elevation gain modest at under 1,000 feet most days. We do have one day with a trying set of uphills. Our gear is shuttled to our next hotel so we only carry what we need for the day. While the hiking is moderate and our itinerary purposefully avoids most of the big uphills, you should be in good enough shape to walk the distances each day as we do not have a support van.
Cultural and Historical Aspects
became known as Francis of Assisi. Born around 1181, he is known for his attempt to broker peace during the Fifth Crusade and his support for the poor, the environment, and animals. The recently-passed Pope Francis purposefully chose Francis as his papal name, given the similarities of their work.
The Via di Franesco is less a time-worn pilgrimage path than a series of historic sites. It also gets a LOT fewer visitors than the Camino de Santiago. Our trip is not a pilgrimage but we do learn about the history of St. Frances and visit the historic sites. However, people were walking on the same trails in the region long before and after Francis, so there is a lot more history to the area than just that era. We learn about modern and ancient Italy, ranging from the pre-Roman Etruscans to World War II resistance by local partisans to Italy’s current place in the world.
The Pleasures of Italy
Part of the joy of any vacation in Italy is, of course, all those joys of Italy. The wine is delicious – in this case often the delectable Sangiovese wines of Tuscany. The cuisine is superb and local to the Apennines mountains: pecorino and fossa cheeses; cappalletti and passatelli pastas; truffles, mushrooms, and chestnuts from the forest. The locals are friendly and always up for a conversation, sometimes only possible by hand gesture. We start our tour in Florence and spend nights in pleasant and comfortable accommodations ranging from a village B&B to a four-star hotel. We eat typically generous Italian breakfasts, packed lunches on the trail, and delicious Italian dinners at local ristorantes, trattorias, and osterias. We’ll end in the small city of Sansepolcro, our local guide Giovanni’s home, and a wonderful place to celebrate the success of our week.
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- Dates: May 3 - 9, 2026
- Cost Per Person: $3,900
- Single Supplement: $800
- Activities: Hiking
- Difficulty: Moderate. You should be in good enough shape to hike the distances each day.
- Guides: Giovanni Ramaccioni
Trip Highlights
- Walk with our local guide Giovanni, learning all about wonderful Tuscany and Italy as we go
- Explore charming villages filled with centuries-old architecture and stories from Italy’s past
- Indulge in local specialties like handmade pasta, truffle dishes, fresh cheeses, and rich wines
- Visit the Camaldoli Monastery and the famous La Verna Sanctuary, sites tied to Francis of Assisi
- Taste beers at a very local small brewery, purchase lunch items at a country butcher, and participate in a cheese making workshop
- Stay in locally owned inns and guesthouses that offer comfort, character, and genuine hospitality
Day 1: CONSUMA PASS TO STIA
Meet in Florence at 8:00 AM and transfer one hour to the Passo della Consuma, a "peaceful place in the middle of nowhere" as one reviewer described it. But for us, it is the perfect place to begin our hiking along the Via di Francesco. Our route twists and turns through forests on the slopes of the Apennines but is primarily a long gradual downhill as we make our way to the town of Stia. Stia is a small town at the confluence of the Arno and Staggia rivers and is a cute town with a central square, half a dozen restaurants and bars, and a few shops. The town is traditionally known for its iron works and wool industry. Our hotel is a stone's throw from Piazza Tanucci, the main square, where you might decide to try a snack of "tortello", the local potato dish, before dinner tonight.
Total Distance: 6.5 Miles and 402 Feet Elevation Gain
We start with a moderate hike that is mostly a gradual downhill with one steep rise to a castle. Options for shorter and longer hikes this day of four and 6.5 miles.
Day 2: LA CALLA PASS TO CAMALDOLI MONASTERY
This morning after breakfast we shuttle 30 minutes to the top of Passo la Calla, which is the border between the provinces of Emilia Romagna and Tuscany and, for us, cuts off a big uphill climb. We start our hike from the pass, with the first half staying up high with only small ups and downs. We are in the UNESCO heritage site called the Foreste Casentinesi that includes Mt Falterona and Campigna National Park, one of the most extensive forests of Europe and dotted with medieval castles, hermitages, and monasteries. During the second half of our hike we descend to the Hermitage and Monastery of Camaldoli. Founded in the 11th century, the hermitage is still operational today. We are able to wander the grounds and visit some of the buildings. At the end of our hike, we will shuttle back to Stia to spend the night there, allowing us not to pack up and check out. We'll again enjoy dinner in a local restaurant.
Total Distance: 7.4 miles and 938 feet of elevation gain
Day 3: MADRIOLI PASS TO LA VERNA SANCTUARY
Today we do check out after breakfast and then again shuttle to the start of our hike, the Passo dei Mandrioli, a 45-minute drive that again removes a big uphill from our day. Our walk stretches along the ridge line offering wonderful views of the valleys of Romagna and Tuscany. We soon cross paths with the “Via Romea Germanica” the pilgrimage route of the medieval German Knights and Princes going to visit the Pope in Rome. We will stop in to a small farm "birrificio" or brewery located along the route for lunch and a tasting. After crossing the beautiful "forest of the fairies" (its almost like the fabled Elves realm in The Lord of the Rings) we will get to the La Verna Sanctuary, one of the most important sites of the St Francis way and of Francis of Assisi. We continue on to our albergo in the village of Chiusi della Verna. This is the only day of our trip with significant uphill, as we have 2,303 feet of gain today.
Total Distance: 10.7 miles and 2,303 feet of elevation gain
Day 4: LA VERNA TO PIEVE SANTO STEFANO
Today we have another wonderful walk, with views of the Upper Tiber Valley. We again are relatively level to start, skirting the beech tree forest that surrounds La Verna, with views of the valley down below. We then have a long gradual descent to a lunch stop at a country butcher, where the butcher himself explains his craft and lays out an incredible spread of local cheeses, pickled vegetables, vino, and about ten varieties of meats. We finish in the town of Pieve Santo Stefano. Pieve Santo Stefano is unfortunately famous in Italy as it was destroyed in 1944 by German troops retreating north. Although the town "lost its past" in some ways, an indirect result is that local citizens created the Piccolo Museo del Diario, the "small museum of diaries", that houses a collection of diaries from everyday people. sent each year to a committee that gives out an annual award. The museum is very well done and will exceed your expectations. Our overnight is in the center of town, with dinner on your own tonight after the big lunch we had.
Distance: 9.0 miles and 736 feet of elevation gain
Day 5: VIAMAGGIO PASS TO MONTAGNA
We again enjoy a plentiful Italian breakfast and check out before shuttling 20 minutes to the Passo di Viamaggio, once again avoiding a sharp uphill climb. Our route today takes us straight through the Alpe della Luna Nature Reserve, a preserve focused on the Alpe della Luna mountains, part of the Apennines. We'll wander through woods and across meadows, with occasional views of the sweeping Tiber Valley below us. We stop at a goat cheese farm embedded within the preserve, where we'll engage in a cheese-making workshop and then eat a delicious lunch of the local products. Our destination tonight is La Montagna, a very small village that was relatively unknown until the growing popularity of the Via di Francesco walking trail. Accommodations are small and we might have to split up between several local B&Bs. Dinner tonight is a treat - we work together to create a typical Italian family-style meal, using the three kitchens at one of our B&Bs and led by our guide (now chef) Giovanni.
Total Distance: 9.3 miles and 1,335 feet of elevation gain
Day 6: MONTAGNA TO SANSEPOLCRO
Today is our final walk, as we finish our Via di Francesco hiking tour en route to our destination of Sansepolcro. We pass through several small villages and then join a small hiking trail. We enter into a forest and pass the Convent of Montecasale, an ancient settlement from the 11th century known for being a major Franciscan site. We then descend to the town of Sansepolcro. Sansepolcro is a small city but distinctly the largest community along our route. It has an amazing Medieval and Renaissance historic center and a fantastic north-to-south "corso", or main street, that draws locals out for a stroll in the evenings. We love Sansepolcro not only because it is such a great city but because it is also away from the typical tourist track. It is also home to Giovanni. We'll overnight in the center of town, probably stop in for a glass of wine at a enoteca, and definitely try the local gelato as we celebrate the last six days.
Total Distance: 7.6 miles and 532 feet of elevation gain
Day 7: DEPARTURE
We have breakfast in our hotel and then transfer to the Arezzo train station, from which you can catch a train to Florence or Rome or perhaps rent a car for your continued travels.
Trip Accommodations
Our accommodations on this tour are relatively simple, given the rural area the hike takes place.
Nights 1 & 2 - Albergo Falterona, Stia: This three-star hotel in the heart of the small town of Stia gets good reviews is perfectly situated for a walk around town. We can enjoy the “fireplace room” that will be great for hanging out after our hike, a small spa, and breakfast on the patio.
Night 3 - Albergo Bellavista, Chiusi della Verna: This village is so small we actually have use of three different B&Bs we can use, depending on our group size and room availability. The Bellavista, as an Albergo, is known for its restaurant serving dishes traditional to the area.
Night 4 - Hotel Santo Stefano, Pieve Santo Stefano: This three-star hotel is situated right in the center of the small town of Pieve Santo Stefano. The hotel is modern with the comforts you would expect.
Night 5 - il Palazzo, La Montagna: This small B&B is located in the middle of nowhere along the Via di Francesco walking route. Hosts Giovanna and Paolo offer clean rooms and a delicious breakfast with homemade pastries. There is not even a website. We also use a second B&B in the area depending on availability and our group size.
Night 6 - Residenza Luca Pacioli, Sansepolcro: This is a brand-new hotel situated in a building from the 1400s. The four-star property has luxurious comforts including large bathrooms and walk-in closets in some rooms.
Book this TourArrival & Departure
We will meet at 8:00 AM in a designated hotel in the city of Florence. Given the early start time, you will very likely arrive the day before and can spend the night at our hotel meeting point or elsewhere in the city. Florence has a major airport but there are no direct flights from the US, so you will likely connect in Rome or elsewhere.
We spend our final night in the town of Sansepolcro and will provide a 40-minute shuttle to the town of Arezzo. Arezzo is on the main train line and you can travel to Florence (1.5 hours or less) or Rome (around three hours). Keep in mind you will need to get to the airport from either city center and some flights leave in the morning, so you might end up spending a final night in Italy. One good option is to fly into Florence and out of Rome.
WHAT'S INCLUDED
- One Zephyr guide will accompany each trip, with a second added as necessary.
- Double occupancy lodging is included. If you are traveling solo, you may ask us to find a traveler to share a room with you but will need to pay a single supplement to have your own room if we cannot match you.
- Five dinners, all breakfasts, and most lunches are included. Gratuity for these meals is also included.
- All your transportation is included once you meet your guides on the first day.
- All group activities are included.
- NOT INCLUDED Beverages, desserts, gratuities to your guides, personal expenses, and travel to and from the destination.
Best time to visit
Tuscany can be hot in the summer and the best times to visit are often the shoulder seasons of April, May, September, and October. However, this itinerary takes place at higher elevation than lower in the Tuscan plains and so is actually a good destination in the summer months. In general, it is possible to hike the Via di Francesco any time between March and October, or even earlier and later in the year.
Extending your vacation
We definitely recommend arriving to Florence two days early. It is an amazing city with much to see and do. We also recommend staying a night in Italy after the tour, potentially in Rome. If you wish to extend your visit outside these cities, a major decision is whether to travel in Italy by train (best for the larger cities) or car (better for rural areas). If you have never visited Tuscany and Umbria, both are amazing regions well worth your time.
Ability Level
This Adventure is rated Moderate. We have utilized shuttles to exclude some of the biggest uphills, making the elevation change quite manageable if you are used to hiking. But hiking 7 - 10 miles per day for six days in a row is challenging.
Type of people who will enjoy this tour
This adventure is ideal for those who have been to Italy before but are looking for a down-to-earth, out-of-the-way region where most people will never visit. You should love wandering the countryside and hiking trails via foot and able to complete the daily distances. The hotels are clean and comfortable but simple, so this is not the location for those looking for five-star experiences.
Changes to Your Itinerary
While everything under “What is Included” will remain the same, the actual restaurants, hotels, and activities listed in our itineraries are subject to modifications. Changes that are out of our control are common – a restaurant closes or loses its awesome chef, a winery changes its visiting hours, a hotel gets remodeled, a road or trail undergoes construction. You are entrusting us to create an outstanding vacation for you and so it is possible we may take the liberty of making necessary changes (even at the last minute, during the guides’ scout trip) to the itinerary that will improve your overall trip experience.
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