Taste of Umbria
An unforgettable cultural exploration of central Italy
Umbria, Italy’s only landlocked region, rewards travelers with enchanting hilltop towns, vibrant local traditions, distinctive cuisine, and exceptional wines—all set within a landscape that feels profoundly authentic. Located just south of Tuscany, Umbria is known as “the Green Heart of Italy,” a region where nature, art, and culinary heritage come together in perfect harmony. This itinerary unlocks the treasures of this lesser-known gem, linking peaceful and scenic bike rides with some of Umbria’s most important towns and villages, renowned wineries, and passionate local producers. Along the way, you’ll experience the region’s rich culture, timeless landscapes, and warm hospitality that define the true spirit of central Italy.
Tour Essence
- Ride through Umbria’s rolling countryside, vineyards, and olive groves in the “Green Heart of Italy”
- Visit Montefalco and enjoy a wine tasting and vineyard lunch at a prestigious Sagrantino producer
- Explore Assisi, a UNESCO World Heritage Site and the birthplace of Saint Francis
- Discover Bevagna and Trevi, two of Umbria’s most charming medieval hill towns
- 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
- Visit the oldest olive tree in Umbria and learn about the region’s centuries-old olive oil traditions
- Experience intimate, local experiences with our friends
- Stay in elegant historic properties, from restored palazzi to a former monastery with a Roman spa
What to Expect
Terrain
Flat with some short climbsStart Location
Spoleto, ItalyEnd Location
Assisi, ItalyMileage
Average Daily: 30 miles Total: 145 milesElevation
Average Daily: 1,600 ft Total: 8,000 ft
Once you have a trip confirmed, we will feed you a steady diet of additional pre-departure information that includes: How to train, prepare, pack and all the wonderful, inspirational and practical things you want and need to know before you go! Our Travel Advisors will be available to help plan your pre- and post-tour travel.
- Expert, bilingual guides
- 1 wine tasting
- Guided walking tour of Assisi
- Group shuttle at the end of the tour
What’s Included
- Use of our exclusive carbon road bike, La Classica Ribelle (or Equivalent Carbon Road Bike)
- Garmin Edge Explore GPS loaded with the GPX tracks of your rides
- Two water bottles
- Saddle bag with repair kit
- Optional: Map holder on handlebar
Pedal Options:
- Flat pedals
- Half-toe pedals (without straps)
What’s Not Included
- Helmet
- Optional: clipless/SPD pedals with shoes
- Optional: your own saddle
- All accommodations
- All breakfasts
- 2 lunches
- 3 dinners
- 1 wine tasting
- Guided walking tour of Assisi
- Savor authentic Umbrian cuisine, from the elegant to home-cooked style via gastronomical explorations
- Experience intimate, local experiences with our friends
Start Location
Spoleto, ItalyFly Into
Florence or RomeEnd Location
Assisi, ItalyFly Out Of
Florence or RomeThe City of Two Worlds
Meals Provided
Lunch, DinnerAverage Mileage
15 milesElevation Gain
1,000 ftRiding Terrain
Rolling hills and one steep climb into SpoletoMeals Provided
Lunch, DinnerAccommodations
Palazzo Leti
Palazzo Leti Boutique Hotel is an elegant 4-star hotel set in a beautifully restored noble residence dating back to the 13th century. Original terracotta floors, exposed wooden beams, and period details reflect its historic character, while its location—just steps from Spoleto’s main landmarks—makes it an ideal base for exploring the city. The hotel’s ornamental Italian garden, with geometric lawns, fountains, and sculptures uncovered during restoration, offers sweeping views of Monteluco and the Umbrian valley below.
The Hill of the Falcon
Meals Provided
Breakfast, Lunch, DinnerAverage Mileage
40 milesElevation Gain
2,000 ftRiding Terrain
2 short climbs in the morning and final climb to MontefalcoMeals Provided
Breakfast, Lunch, DinnerAccommodations
Palazzo Bontadosi Hotel and Spa
Palazzo Bontadosi is a refined 4-star boutique hotel located directly on Montefalco’s Piazza del Comune, with views over the square and the Umbrian valley beyond. Set in a restored noble residence, it combines historic character with contemporary design in chic, comfortable rooms. Its intimate spa, housed in ancient medieval cellars, offers a serene wellness retreat. With its prime location and elegant atmosphere, it feels like your own private palazzo in the heart of town.
Trevi and Bevagna
Meals Provided
Breakfast, Lunch, DinnerAverage Mileage
35 milesElevation Gain
2,000 ftRiding Terrain
Rolling hills with one climb to Trevi and one climb to MontefalcoMeals Provided
Breakfast, Lunch, DinnerAccommodations
Palazzo Bontadosi Hotel and Spa
Palazzo Bontadosi is a refined 4-star boutique hotel located directly on Montefalco’s Piazza del Comune, with views over the square and the Umbrian valley beyond. Set in a restored noble residence, it combines historic character with contemporary design in chic, comfortable rooms. Its intimate spa, housed in ancient medieval cellars, offers a serene wellness retreat. With its prime location and elegant atmosphere, it feels like your own private palazzo in the heart of town.
The City of Francis
Meals Provided
BreakfastAverage Mileage
30 milesElevation Gain
1,600 ftRiding Terrain
Flat and rolling hills and one climb to AssisiMeals Provided
BreakfastAccommodations
Nun Assisi Relais
Located in the highest part of Assisi’s historic center, Relais Nun is an exclusive 5-star resort offering sweeping views from its panoramic terraces. The hotel is the result of a meticulous restoration of the 13th-century Monastery of Saint Catherine, itself built atop 1st-century Roman baths near the ancient amphitheater. Modern, elegantly designed rooms preserve original architectural elements, blending contemporary comfort with centuries of history. The award-winning spa, set within the rediscovered Roman baths, offers a unique experience—soaking among ancient pillars that transport you back nearly two thousand years.
The Valle Umbra
Meals Provided
Breakfast, DinnerAverage Mileage
25 milesElevation Gain
1,400 ft (or optional hike)Riding Terrain
Downhill and flat with one climb to Spello and one back to AssisiMeals Provided
Breakfast, DinnerAccommodations
Nun Assisi Relais
Located in the highest part of Assisi’s historic center, Relais Nun is an exclusive 5-star resort offering sweeping views from its panoramic terraces. The hotel is the result of a meticulous restoration of the 13th-century Monastery of Saint Catherine, itself built atop 1st-century Roman baths near the ancient amphitheater. Modern, elegantly designed rooms preserve original architectural elements, blending contemporary comfort with centuries of history. The award-winning spa, set within the rediscovered Roman baths, offers a unique experience—soaking among ancient pillars that transport you back nearly two thousand years.
