Travel Guides: Italy Travel Guide: Overview
In Southern Europe—right in the heart of the Mediterranean—lies a boot-shaped country stuffed to the brim with culture, history and fine cuisine.
Rolling bike routes through the incandescent Umbrian countryside. Cappuccino breaks in Montefalco and Bevagna. Discover the World Heritage city of Assisi. Ride onward but step back in time as you approach the ancient stones of Gubbio. Then cross the wild Apennine mountains to the coastal wonderland of Le Marche. Olive groves and vineyards roll down to the Adriatic Sea. The food. The people. The landscape. It’s Italy at its finest.
THIS ITINERARY: 6 days, 5 nights
ACCOMMODATIONS: Casual & Casual Plus Hotels
Start Arezzo / End Bologna
Start/End locations may vary. Do not book flights until your trip details are confirmed.
Discover the quiet roads and undulating hills of the Umbrian countryside by bike | Meet our local friends at their farm and enjoy lunch fresh from the garden | Arrive at our elegant retreat in Brufa di Torgiano | Soak up a dazzling 360-degree view over Perugia | Ride tranquil backroads flanked by bright red poppies, cypress trees and picturesque hills | Follow a route through timeless towns like Montefalco and Bevagna | Hearty Italian cuisine awaits in the Valle Umbra | Join a guide for a tour of Assisi, a World Heritage site and one-time home of St. Francis | Pamper your muscles at our hotel’s legendary spa—it’s one of Umbria’s finest!
Sweeping panoramic views over the Umbrian countryside, classic Italian décor and the region's most impressive spa are just a few of the reasons to fall in love with this beautiful resort. (pool, spa)
A scenic climb brings you to lost-in-time lands where shepherds still tend their flocks | Follow breathtaking forgotten roads to hilltop Gubbio, a millennia-old stone village and the cradle of Umbrian civilization | Visit the Palazzo dei Consoli Museum and witness the Iguvine Tables, bronze inscriptions from the 2nd century BC | Savor traditional fare at a ristorante in one of Gubbio’s impressively preserved medieval buildings.
This ancient stone monastery, a Small Luxury Hotels of the World Member, has been transformed into a serene retreat nestled into the hillside above Gubbio's historic town center. (pool, spa)
Pass through the awe-inspiring Furlo gorge as you bike along the Via Flaminia, an ancient Roman road | Cross over the Apennine mountains—Italy’s geographic spine—to Le Marche | Enter an off-the-beaten-path landscape filled with sprawling vineyards, silver-green olive groves and golden wheat fields | Be greeted by the radiant Adriatic coast | Unwind at a 17th-century villa in the village of Trebbiantico | Cycle along the azure Adriatic Sea | Ready for a swim? Do as the locals do and head to the beach | Ride up to San Bartolo mountain and regional park for spectacular coastal views high above the shore | Enjoy a sunset cruise, aperitivo in hand, before dinner in the seaside resort town of Pesaro | Take one final spin through the area’s postcard-perfect hills.
The classic Italian gardens and olive groves that were once part of this 17th-century villa enhance the already picturesque setting of this elegant family-owned hotel. (pool)
The earlier you book, the more choice you'll have and the lower your price. And you can always change your mind — you won't be charged to transfer to a different trip before your final payment is due. View cancellation policy
Click on dates for pricing, itinerary variations and to book your trip. Price is per person, double occupancy.
Every Backroads trip is designed to appeal to a wide variety of interests and fitness levels. We know your pace may vary from one day to the next—and your traveling companion's may differ somewhat from yours. So we present a range of mileage options, and each day you decide exactly what and how much you want to do. LEARN MORE.
We want to make sure you're on the right trip and that you have the best experience possible. Every Backroads trip is unique and this one is no exception.
Our exploration of Umbria and Le Marche brings us from rolling countryside to the Adriatic coast. Most routes travel along beautiful country roads but, on occasion, you can expect to encounter increased traffic as we pass through larger historic towns like Assisi, Perugia and Gubbio. Along the coast near Pesaro, a summer destination popular with locals, we ride on urban bike paths that sometimes intersect with busier roads. Of course, the van is there to support you if you want a lift.