Welcome to Le Marche! Your guides will meet you at your hotel or the train station in San Benedetto del Tronto, on Italy’s Adriatic coast. We’ll get fitted on our bikes and start climbing out of town onto a panoramic ridgeline that quickly leaves the beach-town vibes of San Benedetto behind. Riding through ancient hilltop towns with striking views over vineyards, farms, and olive groves, you’ll wonder how this region has remained a secret for so long. Its isolation has helped preserve local produce like the heirloom pink apples of Montedinove, a town we will ride through. End the ride with a descent into the ancient city of Ascoli Piceno, where we’ll sleep in a historic palace.

Meals: Lunch / Dinner
Destinations: Grottammare, Montedinove, Ascoli Piceno
Accomplished: 39 miles / 63 km, elevation gain: 4,510 feet / 1,375 meters
Accommodations: Palazzo dei Mercanti

Yesterday’s climb departed the coast and today will continue in kind; we’ll leave the cultivated landscapes of the coastal plain and spend the next two days in the wild uplands of the Apennine Mountains. This area has remained unknown to Italians and tourists alike due to its inaccessibility, but on a bike all you need is a strong will and low gear. Climb to the highest point on the trip, Forca di Presta, and discover one of Italy’s best-kept secrets: the hidden valley of Castelluccio. This alpine plain is carpeted with lentils that flower in a riot of reds, blues, and purples; no visit is complete without sampling these local legumes and other mountain dishes at our friend Peppe’s renowned taverna. Tonight we stay in Norcia, the hometown of Saint Benedict and a gourmet capital known throughout Italy for its truffles and cured meats. Check into our Relais & Chateaux hotel and bring out your inner epicure at a Michelin-starred dinner.

Meals: Breakfast / Lunch / Dinner
Destinations: Venarotta, Propezzano, Forca di Presta, Norcia
Accomplished: 55 miles / 88 km, elevation gain: 7,580 feet / 2,311 meters
Shorter Option: 48 miles / 78 km, elevation gain: 6,173 feet / 1,882 meters
Accommodations: Palazzo Seneca

Get ready for the wildest ride of the trip. In ancient times, this corner of the Apennines was home to the Sabine people, a hardy group that gave early Romans plenty of headaches. The area remains largely untamed, with the occasional stone village peeking out of the forests and deep gorges—in 2016, a powerful earthquake rocked these villages and the reconstruction remains ongoing. Stop for a coffee in Borgo Cerreto, where a medieval tower keeps watch from the heights. We’ll return to civilization with a final climb over to Spoleto and the Val Umbra, home to our next hotel. Dinner is as local as it gets: sample wood-grilled dishes and truffles harvested from the surrounding forest at a typical Umbrian restaurant.

Meals: Breakfast / Lunch / Dinner
Destinations: Preci, Borgo Cerreto, Poreta
Accomplished: 50 miles / 80 km, elevation gain: 4,982 feet / 1,519 meters
Accommodations: Borgo Della Marmotta

Pedal today across Umbria, known as the “Green Heart of Italy.” This area was the home of St. Francis and boasts an incredible wealth of both medieval hilltowns and Roman ruins. It is also the source of some of Italy’s best olive oils, wines, prosciuttos, and homemade pastas. Once we’ve left the mountains in our dust, our route takes us along panoramic open ridgelines through olive groves, wheat fields, and oak forests. Cross the upper reaches of the Tiber River before stopping for lunch in the medieval square of Panicale. Take in stunning views of Lake Trasimene as we finish riding to tonight’s hotel, a boutique winery below Montepulciano. Tonight, we delve deeper into the region’s viniculture during a tasting at our favorite Vino Nobile producer, followed by dinner with a garrulous local chef.

Meals: Breakfast / Lunch / Dinner
Destinations: Marcellano, Mercatello, Panicale
Accomplished: 75 miles / 121 km, elevation gain: 5,497 feet / 1,676 meters
Accommodations: Villa Svetoni or Borgo Tre Rose

Today begins with a climb through the heart of Vino Nobile vineyards, along the cobbled streets of Montepulciano, and towards the architectural masterpiece of San Biagio. This unique sanctuary packs 2000 years of history into just 2 kilometers, replete with Etruscan tombs, a medieval façade, and graceful Renaissance belltowers. As we ride out of Montepulciano the landscape broadens to reveal the Crete Senesi, characterized by long vistas, cypress-lined drives, and orderly brick and limestone hilltowns. Jump onto a few sections of the famed Strade Bianche route as we dip into Chianti on our way into Siena. This evening you are free to explore the city’s narrow alleys, soak up the Gothic architecture of the Piazza del Campo and Duomo, and sample the local restaurant scene.

Meals: Breakfast / Lunch
Destinations: Montepulciano, Asciano, Siena
Accomplished: 51 miles / 83 km, elevation gain: 4,979 feet / 1,518 meters
Accommodations: Borgo Grondaie or La Villa di STR

Leaving Siena, we ride past the fairytale fortress of Monteriggioni and onto the ancient Roman road, the Via Cassia—its low highway number (SS 2) a sign of its longevity. Pedal into Canneto, a medieval hilltown that marks the beginning of our descent to the coastal plain. Ride over one last hill and through San Vincenzo to reach the triumphant finish of our epic ride at the Mediterranean Sea. In the last 40 years, this region has risen from obscurity to become famous in the wine world for its production of so-called Super Tuscans like Sassicaia and Ornellaia. We will pair some local Super Tuscans with our final dinner as we celebrate a memorable week of biking, eating, and drinking our way across Italy.

Meals: Breakfast / Lunch / Dinner
Destinations: Monteriggioni, Canneto, San Vincenzo
Accomplished: 77 miles / 124 km, elevation gain: 5,971 feet / 1,820 meters
Shorter Option: 74 miles / 119 km, elevation gain: 5,295 feet / 1,643 meters
Accommodations: Poggio ai Santi or Relais Sant’Elena

Enjoy a relaxed morning, sleep in, and savor a leisurely breakfast at this gorgeous hotel. Mid-morning, we’ll transfer you to Pisa as you head on to your next destination.

Meals: Breakfast
Destinations: Pisa