Rome to Ravenna

On our exclusive journey across the heart of Italy, we discover a spectacular array of hidden treasures, from ancient archaeological sites and extraordinary art and architecture to a palette of exquisite landscapes we explore on foot. We enjoy an insider’s experience as we hike the golden hills of Umbria, explore undiscovered Le Marche, set between the sunny shores of the Adriatic Sea and the 6,000-foot peaks of the Apennines, enjoy spectacular vistas from a mountaintop in tiny San Marino, and marvel at the shimmering frescoes of Ravenna. Our Trip Leaders' passion for la cucina italiana is contagious, and our adventure is complemented by sumptuous meals and fine wines—what would a trip to Italy be without them?

Itinerary at a Glance

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Days 1-2
Rome

We view the staggering monuments of Imperial Rome as we explore the Colosseum, Forum, and Catacombs, and walk the most famous of Roman roads, the Appian Way.

Days 3-4
Sutri / Orvieto, Umbria

Heading north on the Via Cassia, the old Roman road connecting the capital to Etruria, home of the first Roman emperors, we enter Umbria, the “green heart” of Italy. In Sutri, we explore Etruscan tombs and an astonishing Roman amphitheater carved from tufa rock, then hike on a wild trail in the forested hills. Our explorations in Orvieto, set on a sheer crag of volcanic rock, include the stunning Duomo with its glorious façade and a hike around beautiful Lake Bolsena, formed in the crater of an extinct volcano.

Days 5-6
Spello / Assisi

After a hike skirting the Tiber River, we head to Deruta, famous for its hand-painted ceramics. In Spello, a wonderful medieval hilltown hewn of pink stone, we enjoy a gourmet dinner at Michelin-starred La Bastiglia. In Assisi, the birthplace of St. Francis, we explore the Basilica di San Francesco, whose magnificent frescoes by masters of the 13th and 14th centuries are renowned throughout the world. A hike on Mt. Subasio overlooking Assisi grants a breathtaking panorama of golden Umbrian hills and towns.

Days 7-8
Fabriano, Le Marche

Our hikes in Le Marche, an enchanting land of ancient hilltop towns, vineyards, and lavender and sunflower fields, reveal a part of Italy still relatively undiscovered. We also explore Fabriano, famous for its fine paper, and the crystalline wonders of the Frasassi Caves, eerie limestone caverns full of fanciful stalactites and stalagmites.

Days 9-10
Urbino / San Marino

Setting off on foot, we reach the walled town of Urbino, designated a World Heritage Site for its superb Renaissance art and architecture. In the Republic of San Marino, a tiny enclave completely surrounded by Italy, we explore the medieval streets of its historical center, then hike on Monte Titano, with spectacular vistas sweeping all the way to the sea.

Days 11-13
Verucchio, Emilia-Romagna / Ravenna

In Emilia-Romagna, known for its Byzantine and Renaissance art, Romanesque churches, and fabulous food, we enjoy countryside hikes among hilltop towns. Our explorations end in Ravenna, celebrated for its exquisite golden mosaics—the world’s crowning achievement of Byzantine art. Depart on Day 13.

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What the Trip is Like

This trip is Level 3, Moderate. We enjoy day walks and hikes of 2-5 hours over variable hill and mountain trails, with occasional short, steep sections. We will carry just a daypack with trailside essentials such as jacket, water bottle, and camera. Sturdy, well broken-in hiking boots are necessary for the rural trails of this area. The meals included in the itinerary will be taken at the hotels where we are staying or at restaurants in the towns. For dinners “on your own,” the Trip Leader will be happy to recommend local restaurants and trattorias. Please note that in Europe, the dinner hour is considerably later than what it is in the US. We do our best to secure early reservations for our groups, but most often the evening meal will be at 7:30 PM. In an effort to capture the spirit of old Europe, the hotels we use are often family-run converted villas or inns, full of ambiance and colorful local history. Although the rooms are not always of uniform or international size, our leaders try their best to assign rooms in a fair way so that all participants experience an equal advantage throughout the trip as a whole.

Explanation of Trip Levels