Rome to Ravenna

From Rome, where the Roman Empire began, to Ravenna, where it fell, we discover a spectacular array of hidden treasures, including ancient archaeological sites and extraordinary art and architecture along with sumptuous wines and cuisine. Our hikes bring us through a palette of exquisite landscapes, from the rolling hills of Umbria to Le Marche, where the peaks of the Apennines rise from the Adriatic, and from the tiny republic of San Marino to the heartland of Emilia-Romagna, the culinary capital of Italy. Our grand finale is in Ravenna, renowned the world over for its dazzling Byzantine mosaics. This is the dream trip of Trip Leader Gianluca Canalicchio, a native of Rome, who brings his profound awareness of history and passion for wine and cuisine to every aspect of the trip.

Itinerary at a Glance

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Day 1
Rome

We enjoy an introduction to Imperial Rome as we visit the Colosseum, the largest ever built in the Roman Empire, and the Forum, once the center of the Mediterranean world.

Days 2-3
Sutri / Orvieto, Umbria

Heading north on the Via Cassia, the old Roman road connecting the capital to Etruria, home of the ancient Etruscans, 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 facade and a hike around Lago di Bolsena, a beautiful lake formed in the crater of an extinct volcano.

Days 4-5
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 (and perhaps a glass or two of the famed Sagrantino red wine!). In Assisi, the birthplace of St. Francis, we explore the Basilica di San Francesco, lavishly decorated with remarkable frescoes by masters of the 13th and 14th centuries. A hike on Mt. Subasio overlooking Assisi grants a breathtaking panorama of golden Umbrian hills and towns.

Days 6-7
Fabriano, Le Marche

Set between the sunny shores of the Adriatic Sea and the 6,000-foot peaks of the Apennines, Le Marche is an enchanting land of ancient hilltop towns, vineyards, and lavender and sunflower fields. Our hikes here 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 8-9
Urbino / San Marino

A hike along an ancient Roman road brings us to the walled town of Urbino, designated a World Heritage Site for its superb Renaissance art and architecture. Continuing to 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 10-12
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 and visit the ceramics museum in Faenza, where the art of faience originated. Our explorations end in Ravenna, celebrated for its exquisite golden mosaics—the world’s crowning achievement of Byzantine art. Depart on Day 12.

For a more complete description, Download Full Trip Brochure

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