Italy: Sea-to-Sea Bike Tour

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

8 days / 7 nights Level: 4Price From: $5,295Collection: Challenge, Classic

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—including truffles from your very own hunt
  • Traverse the culturally rich and gastronomically influential regions of Marche, Umbria, and Tuscany, over undulating terrain on picturesque back roads, every mile by bike
  • Taste the terroir in local wines as you travel from Le Marche to Tuscany


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 the train station in San Benedetto del Tronto, on Italy’s Adriatic coast. After a coffee, we’ll hop 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. Tonight we celebrate the best of Le Marche’s regional cuisine at dinner with a local winemaker.

    Meals: Lunch / Dinner
    Destinations: San Benedetto del Tronto, Montedinove, Montelparo
    Accomplished: 30 miles / 48 km, elevation gain: 1,221 meters
    Accommodations: Hotel Leone

  • Day 2

    Conquering the Sibillini

    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 Appenine 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. The Fiastra gorge acts as the gateway to this region and we’ll wind our way up the canyon for views of the wild Sibillini Mountains. According to legend, the range is named for the legendary seer, or ‘sibyl,’ who lives in a cave here. This evening, we’ve earned a soak in the soothing pools of our spa hotel before a dinner featuring local products like lentils, cicerchia (a local legume), mountain lamb, and pecorino cheeses.

    Meals: Breakfast / Lunch / Dinner
    Destinations: Falerone, Fiastra, Camerino
    Accomplished: 57 miles / 91 km, elevation gain: 1,573 meters
    Accommodations: Borgo Lanciano

  • Day 3

    Crossing the Hump

    Get ready for the wildest ride of the trip. Our route follows the narrow Sefro Valley up a switchback climb to the mountain pastures of Montelago and over the Passo Sallegri, recently featured in the Tirreno-Adriatico bike race. Descend to the plains of Colfiorito, famed for its red potatoes, and cross into Umbria as we leave the Marche behind. The final push of the day brings us to the highest point of our trip: a view we call “Umbria’s balcony,” where the entire Val Umbra sprawls before you. Tonight we’ll stay at a restored farmhouse that still produces olive oil, grains, and legumes. Needless to say, dinner will feature these farm-fresh ingredients and some local truffles found in the surrounding forests.

    Meals: Breakfast / Lunch / Dinner
    Destinations: Passo Sallegri, Colfiorito, Poreta
    Accomplished: 58 miles / 93 km, elevation gain: 2,101 meters
    Accommodations: Borgo Della Marmotta or Borgo Campello

  • 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. We’ll delve into Umbrian food culture during a truffle hunt with a local tartufaio and his dog before setting off on our ride. 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 arriving at our beautiful country villa near the south shores of Lake Trasimene.

    Meals: Breakfast / Lunch / Dinner
    Destinations: Collazzone, Marsciano, Pietrafitta
    Accomplished: 53 miles / 86 km, elevation gain: 1,237 meters
    Accommodations: Villa Monte Solare

  • Day 5

    Tuscany and the Val di Chiana

    Today we enter Tuscany, the third and final region of our sea-to-sea sojourn. Climb to the hilltown of Panicale before descending into the Val di Chiana, home of the famed Chianina cattle. These huge white cows were the original Tuscan tractors, prized for their ability to pull plows through the thick local soil. Since WWII they have been reinvented as beef cows, most famously as the star ingredient of Bistecca Alla Fiorentina. This area also produces wheat, apples, olives, peaches, and, as you’ll see on our climb to the hilltown of Montepulciano, some of Italy’s standout red wines. Sample some of this local Vino Nobile with our favorite local producer before heading to dinner.

    Meals: Breakfast / Lunch / Dinner
    Destinations: Panicale, Montepulciano, Montefollonico
    Accomplished: 44 miles / 71 km, elevation gain: 1,056 meters
    Accommodations: La Chiusa

  • Day 6

    Siena and the Crete Senesi

    Ride into the classic Tuscan landscape of the Crete Senesi, characterized by long vistas, cypress-lined drives, and orderly brick and limestone hilltowns. On our approach to Siena, the landscape changes once again as the green hills of Chianti emerge. Vineyards and deep forests obscure ancient castles and the wild boar who roam the region, known as cinghiale. No trip to Chianti would be complete without trying cinghiale, especially washed down with world-class Chianti wine. After lunch, it’s a short ride to our hotel in Siena where the afternoon is yours to explore this quintessentially gothic city, have an aperitivo in the Piazza del Campo, and research the local restaurant scene for dinner on your own.

    Meals: Breakfast / Lunch
    Destinations: Trequanda, Asciano, Siena
    Accomplished: 50 miles / 80 km, elevation gain: 1,160 meters
    Accommodations: Borgo Grondaie

  • Day 7

    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 past the impressively perched medieval village of Colle di Val d’Elsa en route to Volterra, an imposing Etruscan hilltown that marks the beginning of our descent to the coastal plain. Ride over one last hill and through Bibbona to reach our final hotel of the tour. 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, Colle di Val d’Elsa, Volterra, Bibbona
    Accomplished: 58 miles / 93 km, elevation gain: 1,434 meters
    Accommodations: Relais Sant’Elena

  • Day 8


    Take a final spin through Bolgheri and down to the beach to dip your front wheel in the Ligurian Sea, officially completing the journey from coast to coast. Later in the morning we will transfer you into the Pisa train station as you head to your next destination.

    Meals: Breakfast
    Destinations: Bolgheri, Pisa
    Accomplished: 17 miles / 28 km, elevation gain: 210 meters

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 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: 1:00 pm

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

2019Single Supplement From: $590

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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 6 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
  • Complimentary DuVine gear, including a custom cycling jersey, 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.

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Synapse Carbon Ultegra Di2

Manufacturer: Cannondale

Type: Road