A Feast in Umbria

An unforgettable cultural exploration of central Italy with Top Guide Andrea Vitali.

A Feast in Umbria

Umbria, Italy’s only landlocked region, rewards travelers with marvelous hilltop towns, lively local traditions and festivals, a distinct and delicious cuisine, and exceptional wine in a setting that embodies authenticity. Located just south of Tuscany, Umbria is known as “the green heart of Italy” and is a region that offers visitors the perfect blend of nature, art, and culinary traditions.

This limited-run itinerary, created and led by Top Guide Andrea Vitali, unlocks the treasure chest of this lesser-known region, linking a variety of peaceful bike rides to some of the most important towns and villages, wineries, and producers. And taking place during Umbria’s most important and lively medieval festival, it’s chock full of great surprises!


  • Taste the region’s premium vintage wines and visit their respective wineries
  • Savor authentic Umbrian cuisine, from the elegant to home-cooked style via gastronomical explorations
  • Experience intimate, local experiences with our friends
  • See recreations of medieval crafts from the "Gaite" festival

Trip Details

Single Supplement
6 days / 5 nights
Athletic Beginner
Total Mileage
145 miles
Daily Average
30 miles (optional extra loops available)
Flat with some short climbs
Start/End Locations
Trip Dates
06/16/19 - 06/21/19

Make this tour Private or for more information, call:



The City of Two Worlds

Benvenuti! Welcome to Umbria! We’ll meet at the Foligno train station and shuttle you to Spoleto, a hilltop town not far from the region’s capital Perugia. Its strategic position along the Flaminian road have made it important since before Roman times. Later from its impregnable walls, the Lombard dukes dominated most of central Italy, and its roman and medieval remains are a testament to its might during the period. Our hotel is located within the walls of the city.

The Hill of the Falcon

Many miles of today’s beautiful ride will be on a completely car-free bike path along the Teverone river, as we enter deep into the heart of the Sagrantino wine area heading towards Montefalco. Sagrantino is the premium DOCG red wine of Umbria and we will visit one of its most prestigious producers, the Antonelli winery for a visit and lunch which includes wine pairings from the vineyard with each course.

Trevi and Bevagna

On the climb up to the village of Trevi, stop to see the oldest olive tree in Umbria and hear about its history. Small countryside roads will take us to a small farm, where we will stop for lunch, meet the family, and feast on the homemade cheese and vegetables straight from the garden. Tonight we’ll have a special musical event to accompany us on another veritable Umbrian Feast.

The City of Francis

Say goodbye to Montefalco as we leave its lovely vineyards and make our way across the tranquil Valle Umbra to Assisi. It's the hometown of Italy’s patron saint, San Francesco, and today we will explore his story and the art his life inspired. Assisi, a UNESCO World Heritage site, is “a series of masterpieces of man‘s creative spirit.” In the afternoon, we’ll visit the Tili family and join them in an unforgettable hands-on cooking class and accompanying dinner. Laughs guaranteed!

The Valle Umbra

Leave Assisi for one last leisurely spin, gently dropping to the valley below, and heading towards the lovely Spello, an old Roman colony and now world famous for its “infiorata” festival. Meander its stone paved streets, ancient buildings, tiny alleyways, just like in the 12th century. In the late afternoon, a local guide will give us a tour of the town focusing on the art the life of St. Francis inspired. Afterwards, we’ll take you to our favorite restaurant in Assisi for our final celebration.


It’s time to say goodbye to Assisi and Umbria. Sleep in a little, or take a stroll to the local corner bar for one last cappuccino with the locals before we shuttle you to the Foligno train station and onwards to your next destination.

What's Included

Trip Planning

  • Use of a carbon road bike equipped with a Garmin Edge Touring GPS
  • Wine kitty and Ciclismo kit (bibs and jersey)
  • Service of a Ciclismo Top Guide throughout the program

On The Tour

  • 2 wine tastings
  • Guided walking tour of Assisi
  • Cooking class at Tili Winery
  • All entries into museums, churches and musical events as listed in itinerary
  • Group shuttles to and from the train station at the beginning and end of the tour

Accomodations & Meals

  • All accommodations
  • All breakfasts
  • All lunches
  • All dinners, with wine included

Meet the Guides