Sansepolcro Hiking & Biking Adventure

Some trips are about a destination. This one is about something more.

In 2027, Zephyr Adventures turns 30 — and we’re celebrating the way we know best: with an extraordinary active trip to a corner of the world that many travelers never visit, accompanied by a friend of ours, Giovanni, whom we have known for over 20 years. This tour is offered exclusively to Zephyr alumni, our way of saying thank you to the community of travelers who made three decades of adventure possible. We hope you’ll join us – book early as we have a maximum of 14 rooms.

The region surrounding Sansepolcro sits in the far eastern edge of Tuscany, pressed against the border with Umbria, cradled by the Apennine hills and the young Upper Tiber River. This is not the Tuscany of tour buses and crowded piazzas. It is quieter, more authentic, and more beautiful for both of those things. Medieval hilltop towns rise above forested valleys. Ancient Roman roads are still walked today. Pilgrimage routes wind through woodland that hasn’t changed in centuries. And everywhere you turn, the food, the wine, and the art carry the unmistakable fingerprint of a region that has literally been producing remarkable things since the Renaissance.

Sansepolcro

Sansepolcro is our base — a small, walled city with a beautifully preserved historic center, a world-class museum, and the kind of daily life that hasn’t been curated for tourists. It is home to Giovanni and Michela, our local partners and dear friends, who have been working with Zephyr Adventures for over 20 years. Many of our alumni have met and grown to love Giovanni, with whom we have run dozens of tours. We decided to offer this as a special 30th anniversary tour so you, our alumni, can travel with Giovanni in his home town and home region. You will not be visiting a destination so much as being welcomed into a place by locals who love the area deeply and have planned an itinerary to share it with you.

Sansepolcro Area Hiking & Biking

Our week moves between hiking and biking depending on the terrain and the day — and each activity reveals a different dimension of the landscape.

The hiking takes you into the Tuscan Apennines on ancient trails, through dense woodlands, past medieval hermitages, and up to ridgelines with far-reaching views over the Valtiberina valley and beyond. The full routes are moderately challenging, shorter options are available for every hike, and you are always welcome to opt out of any activity and spend the time your own way.

The biking follows quiet country roads through olive groves, vineyards, and hill towns that feel genuinely timeless. One day takes you through the Umbrian valley below Assisi on a mostly flat 26-kilometer route. Another covers 35–40 kilometers between Sansepolcro, Citerna, and the historic town of Anghiari, with shorter pickup options available at multiple points along the way. E-bikes are available if needed.

The Culinary Experience

To eat and drink in this corner of Italy is to understand something about the Renaissance that no museum can quite convey: these people believed deeply in doing things well, and that belief extended to the table.

The week includes a private dinner and wine tasting at Cantina La Palerna, a beautiful estate with sweeping valley views. A truffle hunting experience in the woods near Citerna — and a tasting of what you find — offers one of the most memorable food experiences available anywhere in Italy. A visit to the Frantoio di Spello olive oil mill includes a proper tasting of the region’s extraordinary oil. A Sagrantino wine estate in Umbria introduces you to one of Italy’s most compelling and least-known red wines. And then there is the cooking class: the option to learn from chef Alessia, who has spent years researching the foods of this region as they were prepared hundreds of years ago during the Renaissance.

Your Guides

Giovanni Ramaccioni is our Italian specialist and a man of many talents. Not only is he an expert on the food, culture, and history of his country, but he is also an expert on biking, hiking, and this region. He also is intimately familiar with Italian wines and can give you his opinion on why they are much better than French wines! He has guided biking and hiking tours in throughout Italy for decades and knows the area like the back of his hand. Giovanni and his college sweetheart Michela live in Umbria with their two kids.

Towns & Cities We Visit

One of the distinctive pleasures of this tour is the sheer number and variety of historic towns within reach of Sansepolcro — each one with its own character, its own art, its own reason to linger.

Sansepolcro — Our home base for the week. A beautifully preserved walled city, birthplace of Piero della Francesca, with a world-class museum housing his masterwork “The Resurrection.” One of the most authentic small cities in Tuscany, with almost no tourist infrastructure and a daily life that feels entirely genuine.

Anghiari — Perched on a ridge above the Tiber Valley, Anghiari’s medieval streets and views over the surrounding countryside have made it one of the most admired small towns in Italy. The site of a famous Renaissance battle depicted by Leonardo da Vinci.

Citerna — A tiny, perfectly preserved hilltop village with panoramic views over the Tiber Valley into Umbria. Most visitors to Tuscany never find it. We’ll arrive by bike.

Spello — A beautifully intact Roman and medieval town on the slopes of Monte Subasio in Umbria, known for its extraordinary Pinturicchio frescoes and its position at the heart of Umbria’s olive oil country.

Assisi — One of the more famous cities in Italy, known for its patron saint Francis of Assisi. The city also has fantastic, narrow, winding streets and beautiful views over the Umbria valley below.

Bevagna — One of Umbria’s hidden gems: an ancient Roman town in the flat valley below Assisi with a remarkably preserved medieval piazza and craftsmen’s workshops that still operate using centuries-old techniques.

Cortona — The hilltop Tuscan city made famous by Frances Mayes’ “Under the Tuscan Sun,” with sweeping views over the Val di Chiana and one of the most rewarding historic centers in the region. We approach it on foot, hiking up through cypress-lined avenues and ancient Roman roads.

Cultural Highlights

The cultural richness of this tour is as striking as the physical activity — perhaps more so. This region sits at the intersection of Tuscan and Umbrian history, Renaissance art, medieval spirituality, and living traditions.

Piero della Francesca’s “The Resurrection” — Widely considered one of the greatest paintings in the world, housed in the Civic Museum of Sansepolcro. Aldous Huxley called it the greatest painting he had ever seen. Seeing it in the city where Piero was born and lived is an experience of a different order than seeing it in a reproduction.

Hermitage of Montecasale — An ancient Franciscan hermitage tucked into the woodland above Sansepolcro, reached on foot through trails that have been walked by pilgrims for eight centuries.

La Verna Sanctuary — One of the most significant Franciscan sanctuaries in Italy, built on a dramatic forested outcrop where St. Francis of Assisi received the stigmata in 1224. The monastery complex is serene, historically profound, and visually extraordinary.

Pinturicchio Frescoes, Spello — A chapel full of brilliantly preserved Renaissance frescoes by Bernardino di Betto (known as Pinturicchio), one of the most gifted painters of the Umbrian school.

Craftsmen’s Workshops, Bevagna — Living museums of medieval craft: a paper mill using Roman-era techniques, a candle maker, a mosaic workshop. These are working craftspeople, not tourist demonstrations.

Frantoio di Spello Olive Oil Mill — A working olive oil mill where the process of pressing oil from the olives grown on the slopes of Monte Subasio is explained and tasted in full.

Aboca Museum, Sansepolcro — A remarkable museum dedicated to the history of medicinal herbs and natural medicine, housed in a beautifully restored historic building. Aboca is one of Italy’s leading herbal medicine companies and has its roots in this region. We do not visit this museum as part of our tour but it is available to do on your own.