Italy Coast to Coast by Gravel Bike

Itinerary Details

1. Day 1Meet in Ancona and Transfer to Sirolo

   You'll meet in the port city of Ancona, the gateway to the Marche region along the Adriatic coast. From here, you'll be whisked away to Sirolo, a picturesque town nestled further down the coastline. Situated atop cliffs with panoramic views of the Adriatic Sea and featuring a medieval town square, you couldn’t ask for a more scenic launchpad to your cycling adventure. In the evening you'll gather for a trip briefing and welcome dinner.
   

   • Villa Ghirardelli
   • Dinner
2. Day 2Sirolo – San Marcello

   Bidding farewell to the Adriatic coastline, the inaugural ride takes you into the rustic heart of Central Italy. You'll ride on a mix of paved and gravel roads across a landscape of undulating hills in the historic hinterlands of Marche. You'll pause in Offagna, a medieval hilltop village with an excellently preserved 15th-century fortress, 'Rocca di Offagna'. You will also pass by another historic gem, Polverigi, with its distinctive circular old town center. The day's route concludes amidst the green hills of San Marcello for some R&R at a renovated wine estate. Indulge in a glass or two of the estate's exquisite natural wines produced on-site.
   

   • 37.3 miles
   • 229.7 ft
     4,166.7 ft
     3,937 ft
   • Tenuta San Marcello
   • Breakfast, Lunch, and Dinner
3. Day 3San Marcello – Fabriano

   Today you'll head for the eastern foothills of the Apennine mountains, the rocky backbone of the Italian Peninsula. The first half of the ride takes you along a winding network of gravel roads through olive groves and vineyards. These are the valleys where Verdicchio di Jesi – awarded as the second best wine in the world – is produced. As you inch your way closer to the Apennines you’ll stop in the medieval village of Serra San Quirico and discover its narrow streets and piazza. The second half of the ride then takes you into the eastern foothills of the Apennines with longer ascents and descents on gravel roads. A highlight is passing through the Gola di Frasassi, a scenic canyon with rugged limestone cliffs and home to the famous Frasassi Caves. A final climb leads you to Fabriano, Italy’s 'City of Paper' which for hundreds of years was Europe’s most esteemed paper production center. Explore this heritage-infused town before meeting for dinner.
   

   • 38.5 miles
   • 505.2 ft
     6,168 ft
     5,662.7 ft
   • B&B La Portella
   • Breakfast, Lunch, and Dinner
4. Day 4Fabriano – Cannara

   From Fabriano, you'll take a few km of paved secondary roads before switching to gravel roads that cross the Apennines. You'll now find ourselves in Umbria, Italy’s green heart, filled with beautiful rolling hills covered with forests, farmland, and villages. You'll ride up and down the region’s quintessential 'white roads' for around 40 km, punctuating this stage with a fun (and bumpy!) descent to the historic town of Assisi. Nestled in the western slopes of the Apennines, Assisi was the birthplace of St. Francis, founder of the Franciscan Order, to whom the town’s beautiful Basilica – a UNESCO World Heritage Site – is dedicated. You’ll spend some time uncovering Assisi’s architectural, religious, and artistic splendors before a gentle finish to today’s ride through the Umbrian countryside. You'll spend the night at an elevated farm stay surrounded by olive groves near the town of Cannara. You can enjoy homemade olive oil and ,of course, some fine local wine!
   

   • 47.2 miles
   • -393.7 ft
     4,921.3 ft
     5,315 ft
   • Incanto della Natura
   • Breakfast, Lunch, and Dinner

   • 

     Comfortable Lodgings

     Stay at lovely agriturismo spots along the way

   • 

     Comfortable Lodgings

     Stay at lovely agriturismo spots along the way

5. Day 5Cannara – Montepulciano

   From Cannara you'll ride through one of Umbria’s prime winegrowing regions and, after around 60 km, you’ll reach Central Italy’s largest lake, Trasimeno. It is also the fourth largest lake nationwide though compared to its more well-known counterparts exudes a calmer and more low-key ambiance. Trasimeno’s gentle, shallow waters and string of medieval towns dotting the marshy shoreline make for a lovely backdrop. You'll trace part of the lake via a dedicated bike path before veering west to enter Tuscany where you'll hop onto the so-called 'land reclamation path', a network of mostly gravel roads following an ancient canal which turned this area of Tuscany from wild valleys into an agrarian hinterland with farms and vineyards as far as the eye can see. You'll conclude the ride in Montepulciano, a town of mixed medieval and renaissance character located high up on a rocky ridge overlooking the iconic Tuscan countryside. It’s hard to dream up a more picture-perfect locale to conclude and celebrate today’s long ride! With plenty of osterias to choose from, dinner is on your own tonight. Make sure to pair with the Vino Nobile di Montepulciano, the town’s signature wine.
   

   • 55.9 miles
   • 771 ft
     3,937 ft
     3,166 ft
   • Palazzo Tombesi Trecci
   • Breakfast and Lunch
6. Day 6Montepulciano – Montalcino

   Today you'll ride the famous white roads of Tuscany, made popular by the L’Eroica and Strade Bianche cycling events. These twisty, undulating chalk roads wind through Tuscan hills and vineyards, offering a challenging yet dreamy ride. But you aren’t racing! You’ll be taking your time to savor the roads and the places they lead to. The first stop is Pienza, 'the ideal town', so named due to its conception by a 15th-century pope as an exemplary Renaissance urban space. This pope would be happy to know that Pienza is now listed as a UNESCO World Heritage Site. You'll then cross Val d’Orcia – with its iconic cypress trees lining the roads – to reach the village of Buonconvento which is surrounded by a still intact 14th-century defensive wall. The final stretch takes you on a winding climb to the fairytale hilltop town of Montalcino. Beyond the charm of its setting and historic piazza, the town is best known for being the home of one of Italy’s most renowned wines: Brunello di Montalcino.
   

   • 37.3 miles
   • 
     4,265.1 ft
     4,265.1 ft
   • Albergo il Giglio
   • Breakfast, Lunch, and Dinner
7. Day 7Montalcino – Scansano

   From Montalcino, you’ll be “treated” to a few km of asphalt before returning to Tuscan gravel roads. Not too long into the ride you’ll see the imposing Abbey of Sant'Antimo rise above the rolling hills. Benedictine monks still reside in the abbey and perform Gregorian chants in the Romanesque church. You'll then continue to the castle of Porrona, a beautifully restored 13th-century Sienese stronghold. From here onwards you'll traverse the Maremma, a pristine and lesser-known region of southern Tuscany with dense forests. This wilderness will be your home for tonight as you'll go glamping at a nature lodge nestled in the Maremma hills near Scansano. The property is only accessible by off-road vehicle, offering a truly remote experience in the heart of Italy.
   

   • 47.8 miles
   • -524.9 ft
     4,527.6 ft
     5,052.5 ft
   • Tenuta San Ludovico
   • Breakfast, Lunch, and Dinner
8. Day 8Scansano – Porto Santo Stefano

   It is time for the home stretch as you'll cycle to the Tyrrhenian coast. From the forests of Maremma, you'll have a final climb to the town of Scansano, famous for producing Morellino di Scansano, a beloved Tuscan wine. You'll then enjoy a mostly downhill ride to the coast, soaking in the final views of the Tuscan hills, vineyards, and charming historic villages. Once you reach sea level you'll cross onto the Argentario promontory. This rugged headland offers a grande finale to the adventure as you'll be welcomed by the azure waters of the Tyrrhenian Sea. High fives are surely in order when you saddle-off in the coastal town of Porto Santo Stefano where you’ll celebrate your journey with a farewell dinner.
   

   • 43.5 miles
   • -1,256.6 ft
     2,024.3 ft
     3,280.8 ft
   • Bike&Boat hotel
   • Breakfast, Lunch, and Dinner
9. Day 9Porto Santo Stefano Departure

   Arrivederci! Feel free to extend your stay and relax by the sea or travel onwards to your next destination in Italy or beyond. Arrangements for transfers or post-tour hotels can be made.
   

   • Breakfast