The Italy Coast to Coast Cycling Tour Itinerary

Day 1 Welcome Day

Welcome! Arrive, settle in, and then get your bike ready before a welcome dinner.
Overnight Location: Hotel in Bibbona
Distance: None
Meals: Dinner

Day 2 Cycling to Volterra

Your first stage takes you from Bibbona to Volterra. You’ll leave Bibbona and head to Bolgheri, where you’ll ride through famous vineyards. These vineyards are known for the Sassicaia wine they produce. The first easy climb takes you to the Castagneto Carducci. Here, you’ll start a spectacular segment on a mountain ridge road. Then, you’ll ride through the wilderness area of Larderello where 12% of the world’s geothermal energy is produced.

Finally, the enchanting Volterra and your luxury accommodation await.
Overnight Location: Hotel in Volterra
Distance: 82km
Meals: Breakfast, dinner

Day 3 Siena City

After breakfast, you’ll head to Siena. This stage starts with a long descent towards the Colle Val d’Elsa. Here, you’ll start a gradual climb through a scenic natural area. Ride on peaceful back roads through old historic villages.

Siena, a city famous all over the world, is today’s destination. In the evening, dine in the old city center and visit the Duomo, Piazza del Campo, and many other beautiful sites.
Overnight Location: Hotel in Siena
Distance: 75km
Meals: Breakfast, dinner

Day 4 Riding through the Heart of Tuscany

Today you’ll ride through some of the most famous scenery in the world, the heart of Tuscany. Pedal over breathtakingly beautiful rolling hills and past old farms with their characteristic vineyards, olive trees, and rows of cypress trees.

Your first stop is Asciano for a light lunch in the old medieval center. This is an easy stage with frequent ups and downs. The important town of Montepulciano is waiting for you next. This extraordinary Tuscan town is of Etruscan origin. One of the most appreciated wines in Tuscany, the Vino Nobile di Montepulciano, is named after the town.

Take some time to visit the historic buildings and the medieval old downtown.
Overnight Location: Hotel in Montepulciano
Distance: 77km
Meals: Breakfast, dinner

Day 5 Cycling to Assisi, Umbria

In this stage, you’ll leave Tuscany and enter Umbria, the Green Heart of Italy (Il Cuore Verde d’Italia).
This is a long stage, but it doesn’t demand long climbs. Go from Montepulciano to Lake Trasimeno, the biggest lake in Central Italy, where you can either have lunch or grab a coffee in one of the numerous bars and restaurants beside the lake.

Back in the saddle, cycle through the welcoming scneery of green Umbria with its undulating hills and welcoming old villages. Early on, you can already see Assisi in the distance, perched on a hilltop at the base of the Monte Pasubio. Assisi is one of the most important cultural cities in Italy. San Francesco d’Assisi was born here, also making it an important religious center.

After a visit to the city, a delicious dinner and some priceless Umbrian wine are your reward after this long stage.
Overnight Location: Hotel in Umbria
Distance: 90km
Meals: Breakfast, dinner

Day 6 Long Climbs Cycling to Norcia

Today, you will enter the Apennine Range, a long mountain range that runs from north to south through Italy. If you want to go from the Tyrrhenian Sea to the Adriatic Sea, you have to ride over these wild mountains. This stage gives you your first taste of the mountains. Encounter a different kind of cycling defined by long climbs with a moderate gradient, always surrounded by an extraordinary landscape.

Your destination is the cultural town of Norcia at the foot of the Monti Sibillini and inside the Monti Sibillini National Park.
Overnight Location: Hotel in Perugia
Distance: 80km
Meals: Breakfast, dinner

Day 7 Alpine Rides to Camerino

Majestic mountains welcome you as you pedal on one of the most spectacular mountain roads in Central Italy. Leave Norcia in the morning and head to Castelluccio di Norcia. This fairytale village is perched on a hilltop in the Piano Grande plateau in a high mountain environment. You’ll start up a road that takes you from the Valley of Norcia to the plateau, a long mountain road with a breathtaking view of the valley.

Once you reach the plateau, you’ll ride up to Castellucio. This area is famous for its lentil plants that offer an incredible visual experience for visitors who pass through during the spring bloom. You then leave the mountains for a long descent to Camerino. You are now in a new region, the Marche, known as the Sweet Region (La dolce regione).
Overnight Location: Hotel in Marche
Distance: 84km
Meals: Breakfast, dinner

Day 8 Cycling to Pergola

The Marche is an incredible region of rolling hills, mountains, and coastline. It may be less famous than Tuscany, but it is undoubtedly of equal beauty. In this stage, you ride inside the Regional Park of Gola Rossa e di Frasassi, a natural canyon between mountains. Ride on peaceful back roads through quiet old villages.

Your final destination is a farmhouse where you can rest and taste local organic dishes and wine.
Overnight Location: Hotel in Pergola
Distance: 76km
Meals: Breakfast, dinner

Day 9 Cycling to Adriatic Sea

The final stage of the tour has arrived! This stage takes you from the heart of the Marche to the spectacular Adriatic Sea with its sparkling green water. Today caps off a long cycling tour through historic towns and unique and extraordinary landscapes, over mountains and hills, and from sea to sea. Savor your last ride!
Overnight Location: Hotel in Marche
Distance: 55km
Meals: Breakfast, dinner

Day 10 Departure

After an unforgettable experience, it’s time to depart. After breakfast, head to the Ancona airport or train station.
Overnight Location: None
Distance: None
Meals: Breakfast