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 Castello di Frontone, a magnificent medieval castle perched atop a rocky outcrop and surrounded by breathtaking scenery. Rich in history, beauty, and character, it provides the perfect setting to experience authentic Italian hospitality while refueling with a fresh regional pasta dish. This afternoon, the route winds through the dramatic landscapes and rugged cliffs of Monte Cucco before arriving at our luxurious hotel, located just outside the beautiful medieval town of Gubbio. Take in sweeping views of the surrounding countryside and the towering Monte Ingino from the hotel's terrace before ending the day with a traditional Umbrian dinner at your leisure in the 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, as today showcases the very best of Umbria: sweeping vistas, vineyard-covered hillsides, majestic fortresses, and some of the region’s most celebrated hilltop towns. Your first stop is Todi, an elegant medieval gem renowned for its beauty, history, and timeless atmosphere. Take time to wander its picturesque piazzas and narrow streets before enjoying lunch at a restaurant of your choice. Leaving Todi, we’ll descend to the Tiber River before climbing once again onto the scenic ridge leading to Orvieto, one of Italy’s most spectacular hill towns. Built on ancient Etruscan foundations, Orvieto rises dramatically above the Paglia River Valley atop sheer volcanic tufa cliffs. Its magnificent cathedral, labyrinth of underground passages, and remarkably preserved medieval center make it one of the cultural highlights of the journey. Don’t miss the opportunity to discover the town’s fascinating history on a walking tour with a local guide. This evening is yours to explore Orvieto at your own pace and select the perfect dinner from one of the many outstanding restaurants tucked within its historic streets, with recommendations from your guides.

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, the centuries-old "dying city" dramatically perched atop a crumbling volcanic plateau and accessible only by a narrow pedestrian bridge. From here, the route rolls through the scenic countryside on a series of gentle climbs before descending to the tranquil shores of Lake Bolsena, Europe's largest volcanic lake, renowned for its crystal-clear waters and breathtaking scenery. Enjoy a relaxing pause by the lake before sitting down to lunch at a local agriturismo. This afternoon, tackle your final climb into Tuscany through forested hills on your way to Manciano, the end of our ride. A 40-minute shuttle then takes you to the Orbetello Peninsula, where you'll complete your coast-to-coast journey from the Adriatic to the Tyrrhenian Sea. Our final hotel provides a spectacular setting to celebrate the achievement. Dip your toes in the Tyrrhenian Sea, raise a sunset cocktail, and toast an unforgettable week of Italian cycling before gathering for an elegant farewell dinner.

Please note: Today's ride concludes in Manciano rather than continuing to the coast. Please refer to Know Before You Go for more details.

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!