Overview

We begin our coast-to-coast ride in Pesaro, the “Cycling City.” Your Trek Travel guides will meet you in the lobby of the Charlie Urban Hotel at 9:00 AM, After a brief round of introductions, your guides will review bike safety, share helpful tips for riding in Italy, and get you comfortably fitted on your Trek bike. Once everyone is ready, you’ll head out on your first ride from straight from the hotel, leaving Pesaro behind as you head into the countryside of the Le Marche region. A steady climb leads to sweeping views of patchwork farmland before the final ascent toward Urbino. We'll stop for lunch just outside the town’s defensive walls, then enjoy a short ride through the alleys of this beautifully preserved Renaissance center on the way to our hotel in the historic heart of town. Tonight, explore Urbino—designated a UNESCO World Heritage Site—and enjoy dinner at a small bistro tucked along its winding cobbled streets. Rest up; this is only the beginning of an incredible week of cycling.

Overview

Today’s ride takes you into Umbria and the Parco del Monte Cucco before tackling Passo Madonna della Cima, our first pass in the Apennine mountains. We'll stop for lunch at an 11th-century monastery surrounded by magnificent woods and rich in history, beauty, and charm. We'll experience the authentic Italian hospitality as we refuel with a fresh pasta of the region or Torta al testo, a typical Umbrian flatbread. This afternoon's ride winds through the jagged cliffs of the Monte Cucco and to our luxurious hotel, which is situated just a short distance from the beautiful medieval town of Gubbio. Enjoy views of the surrounding mountains, including the towering Mount Ingino, from the hotel terrace before indulging in a traditional Umbrian dinner at your leisure at our hotel’s acclaimed Nicolao restaurant.

Overview

Enjoy an active recovery day today. Following breakfast, the ride begins with a gentle warm-up before climbing along quiet, timeworn roads that weave through tiny Umbrian villages. Take in the peaceful mix of woodlands, rugged farmland, and olive groves, then enjoy a relaxed descent with sweeping views of Assisi from above. We'll ride into this remarkable medieval town—best known as the birthplace of Saint Francis, Italy’s patron saint—before continuing to our country resort surrounded by vineyards and olive groves. A casual buffet-style lunch awaits, followed by a restorative afternoon at the hotel’s wellness centre. Later, we’ll shuttle back to Assisi for a guided walking tour through its cobbled streets, ending at the celebrated Basilica of Saint Francis, a UNESCO World Heritage Site. This evening, we’ll dine together in town before settling in for a restorative night as you gear up for tomorrow’s ride.

Overview

Our ride begins with an easy 12-mile (20-km) cruise through the fertile valley below Mount Subasio before the climbing sets in. Keep your camera handy—today is full of sweeping viewpoints, hilltop towns, and hidden fortresses as we pedal through the very heart of Umbria. Take a break in Todi, an elegant medieval village overlooking the Valtiberina (the Tiber River Valley), and enjoy lunch at a restaurant of your choice. Leaving Todi, we’ll descend to the Tiber River and then work our way back up to the picturesque ridge that leads us into Orvieto. Built on Etruscan ruins, the town rises 1,500 feet (450 m) from the floor of the Paglia River Valley and sits atop steep tufa cliffs, its medieval walls and houses carved from the same stone. Don’t miss the chance to learn more about this remarkable place on a walking tour with a local guide. This evening is yours to choose the perfect dinner in town, with your guides’ top recommendations.

Overview

After a freshly baked cornetto and the perfect cappuccino, begin your day with a climb from Orvieto to Bagnoregio, where you’ll take in the striking sight of Civita di Bagnoregio—a centuries-old “ghost town” perched on crumbling rock and reached only by a narrow causeway bridge. The ride continues over a series of rolling climbs before descending to the serene shore of Lago di Bolsena, the largest volcanic lake in Europe. Enjoy a quiet pause here before settling in for lunch at an agriturismo, then tackle your final climb into Tuscany through the forested slopes leading to Manciano. Avid riders can choose to continue all the way to the Orbetello peninsula, completing the full coast-to-coast ride by bike. This evening, dip a toe into the Mediterranean and celebrate with a sunset cocktail as you toast an unforgettable week of Italian cycling.

Overview

This morning, linger over breakfast with some extra pastries, fresh fruit, and perhaps a second cappuccino while you soak in the gorgeous views from the patio. A late check-out time (12:00 PM noon) will allow you to lounge by the pool that overlooks the Mediterranean Sea. Before you bid your farewells, stroll through the grounds of the hotel one last time and savor the idyllic landscape of the Orbetello peninsula. You'll never forget this incredible experience of your bike trip across Italy!