Arrival in Ancona. Transfer at 5 p.m. to Sirolo from Ancona train station, or independent transfer possible by bus or taxi. Meet-up in Sirolo with a Basecamp representative for an aperitivo, bike fitting and briefing before departure. Overnight at Villa Ghirardelli or similar B&B.

• Accommodations: Agriturismo with pool or B&B in Sirolo
• Meals: Breakfast

Wake up to watch the sunrise from the center of Sirolo. 60km of secondary roads, alternating asphalt with gravel roads, villages, and castles, lead you to your first stop: San Marcello. Along the way, you'll pass through Offagna, a village perched on a tufa rock, and Polverigi, one of Ancona's castles. Optional: Wine tasting at Tenuta di San Marcello.

• Daily distance: 36 mi / 58 km
• Elevation gain: 3937ft / 1200 m
• Accommodations: Agriturismo in San Marcello
• Meals: Breakfast

Ready to tackle winding gravel roads through gentle hills, approaching the Apennine mountains. After a few kilometers, you enter gravel roads crossing valleys where Verdicchio di Jesi is produced, awarded as the second-best white wine in the world. You'll pass through charming hillside landscapes, olive groves, and vineyards until reaching Mergo. After visiting the village, you begin the climb on a gravel road, leading you to the descent and into the Gola di Frasassi, a unique canyon housing the spectacular Frasassi Caves.You cannot miss a visit to Valadier Temple, a pearl nestled into a cave with an outstanding view.

• Optional: Verdicchio di Matelica tasting in the charming setting of Fabriano's historic center.

• Daily distance: 37 mi / 60 km
• Elevation gain: 4921ft / 1500 m
• Accommodations: Agriturismo in Fabriano
• Meals: Breakfast

After the first kilometers of asphalt secondary roads, you traverse the gravel roads of the "green heart of Italy" to reach Assisi, descending through rough terrain to the historic village nestled on the slopes of Subasio. The village offers plenty of opportunities to taste local products. You'll ride through the Umbrian countryside until you reach Cannara.

• Daily distance: 47 mi / 76 km
• Elevation gain: 4921ft / 1500 m
• Accommodations: Agriturismo or B&B in Cannara
• Meals: Breakfast

Starting from Cannara, you pass through Torgiano, known for the production of Sagrantino wine. Arriving at Lake Trasimeno, you enter Tuscany. Cycling through endless farms and vineyards, you arrive at Montepulciano, a medieval village between Valdichiana and Val D’Orcia. You'll savor the Vino Nobile di Montepulciano before continuing your journey.

• Daily distance: 56 mi / 90 km
• Elevation gain: 4068ft / 1240 m
• Accommodations: B&B in Montepulciano
• Meals: Breakfast

The sixth day is dedicated to the famous gravel roads of the Eroica, a journey into the essence of the legendary Tuscan landscape. After a coffee break in UNESCO World Heritage Site Pienza, you cross Val d’Orcia to Buonconvento. Continuing on the Eroica gravel roads, you encounter a winding climb, the final challenge before reaching Montalcino.
Optional: Brunello di Montalcino tasting.

• Daily distance: 37 mi / 60 km
• Elevation gain: 4265ft / 1300 m
• Accommodations: Hotel in Montalcino
• Meals: Breakfast

From Montalcino, you enter the hinterland of Grosseto's Maremma, where you find the Castle of Porrona, a gem from the 13th century built by the Sienese. Cycling through the wild Maremma, you pass through a nature reserve of rare beauty.
Optional: Morellino di Scansano wine tasting.

• Daily distance: 48 mi / 77 km
• Elevation gain: 1312ft / 400 m
• Accommodations: glamping site in Scansano
• Meals: Breakfast

You prepare for the final climb to Scansano, then descend past charming villages of Pereta and Magliano, cycling along a scenic road to the Argentario promontory on the Tyrrhenian coast. Porto Santo Stefano is the destination for this last day, concluding with the magic of the sunset over the Tyrrhenian Sea. The journey through the beauty, flavors, and aromas of these marvellous regions—Marche, Umbria, and Tuscany—comes to a sweet conclusion.

• Daily distance: 43 mi / 70 km
• Elevation gain: 2024ft / 617 m
• Accommodations: Hotel in Argentario
• Meals: Breakfast

Bike return and transfer to Grosseto train station or Perugia airport.