Overview

We start our coast to coast journey in the beach town of Pesaro, dubbed the "Cycling City", where you'll meet your Trek Travel guides and fellow cyclists, followed by some time to be fit and familiarized with your Trek bicycle. This morning’s ride starts from the Charlie Urban hotel (or Nautilus hotel on select dates) heading out of Pesaro towards the countryside of Le Marche region. Climb up to enjoy the panoramic views of picturesque farmlands before beginning your final climb toward Urbino. As you start to approach the walled city of Urbino, high up in the distance, you'll pause for lunch and enjoy a traditional meal with a modern spin. After lunch, finish by riding into the beautifully-preserved Renaissance town that has been attracting artists and scholars since the 15th century, from all over Italy and beyond. Tonight, we’ll explore this UNESCO World Heritage Site and dine in a small bistro along winding cobbled streets. It is like a step back in time, where houses and palaces of weathered brick and pantile roofs cluster around steep narrow streets, with misty mountains stretching mysteriously beyond, like the background of a Rafael portrait. This is only the beginning so rest up tonight for more incredible cycling tomorrow.

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 mountains and Mount Ingino from the hotel terrace before joining the group for a traditional and delicious Umbrian dinner at our hotel’s acclaimed Nicolao restaurant.

Overview

Enjoy an active recovery day today. The ride starts with a gentle warm up and then climbs along forgotten roads through tiny Umbrian villages. Experience the tranquility of the woods mixed with views of rugged farmland and olive groves, then savor a relaxing descent as you inhale the views of Assisi from above. This stunning medieval village is best known as the birthplace of Saint Francis, Italy’s patron saint, and it is your lunch destination for this afternoon. Choose your own lunch at one of Assisi’s many trattorias and take some time to explore its Roman ruins and sacred shrines. After lunch, it’s a short descent to the quiet hillside town of Spello, our home for the evening. In the afternoon you have the opportunity to relax, recuperate, and recharge your energy at the hotel's fabulous spa. This evening is yours to find the perfect dinner in town as you admire Spello's well-preserved Roman gates.

Overview

Our ride begins with an easy 12 mile (20 kilometer) cruise through the fertile valley below Mount Subasio before the climbing begins. Remember your camera today as there is no shortage of views, including hilltop towns and hidden fortresses, as we ride through the very heart of Umbria. Take a break when you reach Todi, an elegant medieval village overlooking the Valtiberina (the Tiber River Valley), and refuel with lunch at a restaurant of your choice. Leaving Todi, we will descend to the Tiber River and then work our way back up to the picturesque ridge that delivers us to Orvieto. Built on Etruscan ruins, this town rises 1,500 feet (450 meters) from the floor of the Paglia River Valley, and sits atop almost vertical faces of tufa cliffs. It's surrounded by defensive walls and medieval houses made out of the same tufa rock. It's truly astounding. Tonight enjoy a stroll in this enchanting town, before meeting the group for an aperitif followed by dinner featuring traditional Umbrian fare.

Overview

After a freshly baked cornetto and the perfect cappuccino in our hotel’s frescoed refectory, start your day with a climb from Orvieto to Bagnoregio, where you’ll behold the ancient ghost town of Civita di Bagnoregio, perched precariously upon eroding rock and reached only by a causeway bridge. Your ride continues with a few rolling climbs until you descend to the serene shore of Lago di Bolsena, the largest volcanic lake in Europe. Enjoy a quiet break here before lunch at an agriturismo and your final climb into the region of Tuscany through the forested slopes up to Manciano. Finish your epic journey on the stunning Orbetello peninsula. It's time to dip a toe into the Mediterranean and celebrate in style with a sunset cocktail and toast to a week-long coast to coast Italian cycling adventure!

Overview

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