Italian Coast-to-Coast Journey Bike Tour

From the Adriatic Coast to the Ligurian Sea: Through the Heart of Central Italy

7 days / 6 nights Level: 4Price From: $5,495Collection: Challenge

Tour Highlights

  • Ride east to west across the breadth of Central Italy, from the Adriatic to the Ligurian Sea and across the Apennine Mountains
  • In gardens and kitchens across the region, sample cyclist-friendly dishes from fresh, local ingredients
  • Traverse the culturally rich and gastronomically influential regions of Le Marche, Umbria, and Tuscany, over undulating terrain on picturesque back roads, every mile by bike
  • Taste the terroir in local wines, like our friend Vittorio’s handcrafted bottles at his 13th-century cellar
  • Pedal through the flower-filled mountain splendor of Castelluccio and spend a luxurious night in medieval Norcia
  • Ride like a pro in custom Rapha x DuVine gear: jersey, socks, and cycling cap are complimentary on all Level 4 tours


Pecorino cheese, truffles, hand-made pasta, roasted lamb, bistecca alla Fiorentina, olive oil, seafood, and lentil soup


Verdicchio, Sagrantino di Montefalco, Syrah from the Val di Chiana, Vino Nobile, Chianti Classico, and Super Tuscans

As featured in:
Print Itinerary
  • Day 1

    The Climb Begins

    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

  • Day 2

    The Secrets of Castelluccio

    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

  • Day 3

    Crossing the Hump

    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

  • Day 4

    The Green Heart of Italy

    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

  • Day 5

    Siena and the Crete Senesi

    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

  • Day 6

    Siena to the Sea

    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

  • Day 7


    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: BreakfastDestinations: Pisa

DuVine itineraries may be subject to slight route changes, hotel substitutions, and other modifications.

Arrival Details

Airport City: Rome, Florence, Bologna, or Milan, Italy Pick-Up Location: San Benedetto del Tronto station or Hotel Parco dei Principi in Grottammare Pick-Up Time: 9:00 am
Departure Details

Airport City: Rome, Florence, Bologna, or Milan, Italy Drop-Off Location: Pisa train station Drop-Off Time: 10:00 am

Please note that Arrival + Departure Details for 2025 tours could be subject to change.
Travelers Take Note

Upon booking this tour, you will be asked to complete a short form. We use this information to ensure all Level 4 trip participants are adequately prepared for our most difficult riding and have proximate cycling experience to the rest of the group.

Road quality in Umbria has been impacted by the 2016 earthquakes in the region.

Please note that e-bikes cannot be reserved for this tour.

Any scheduled tour can be made private. Your group, your dates. Go Private

2024Single Supplement From: $950

See our cancellation policy

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  • Thoughtfully selected accommodations that reveal the true character of the region in ideal riding locations
  • Luggage transfers


  • Daily breakfasts, all lunches, and 5 cyclist-friendly dinners at our favorite local restaurants and renowned culinary establishments
  • Nutritious energy snacks, hydration, and shakes to support endurance and recovery
  • Local wines and beer with every meal


  • Wine tastings and activities as outlined in the tour itinerary
  • Entrance fees to historic sites, museums, parks, and all other exclusive events
  • Gratuities for baggage, porters, and hotel service


  • Top-of-the-line Cannondale carbon fiber road bike
  • Exclusive Rapha x DuVine jersey, socks, and cycling cap
  • Complimentary DuVine gear, including a DuVine t-shirt, water bottle, and drawstring bag
  • GPS with pre-programmed route maps


  • Expert bilingual guide with extensive cycling experience and local knowledge
  • Support vehicle that follows the day’s route, distributes refreshments, and offers lifts
  • Pick-up and drop-off before and after your tour from predetermined meeting points
  • Laundry service provided mid-week
  • Daily bike maintenance to ensure optimal performance

See our FAQs page for answers to common questions.

See FAQs

Synapse 2 RLE

Manufacturer: Cannondale

Type: Road

Included in trip price