Italy Coast to Coast Adventure: Ultimate Cycling Tour

Welcome to Italy!

We will have organised a transfer to pick you up from Pisa airport or train station and bring you to the hotel, where our expert guides will be waiting to meet you.

You’ll then sit down for a welcome meeting as the team briefs you on the week ahead and help you set up your bikes ready for the first ride of your trip. If there is enough time left in the afternoon, you’ll be able to take your bike for a warm-up spin around the local area and get a feel for the rest of the tour.

In the evening you’ll rejoin your group for a welcome dinner where you can continue getting to know your fellow tour members.

The first day of your tour will kick off with a wonderful ride from Bibbona to Volterra. We will head out in the morning towards Bolgheri and ride through the beautiful landscape of sun-kissed vineyards, famous for producing “Sassicaia” wine, widely accepted as one of the worlds best Cabernet Sauvignon wines.

The first climb of the day is an easy one, ascending to the town of Castagneto Carducci, from where we will ride a stunning segment along a mountain ridge road, enjoying spectacular views across the countryside. 

We will soon arrive in the rugged Larderello region, home to the oldest geothermal plant in the world, before reaching the enchanting mountaintop town of Volterra and our luxury hotel waiting to welcome us at the end of our first day in Tuscany.

Before starting our ride on Day 3, we will fuel up well at the hotel with a hearty breakfast, before grabbing our bikes and heading out towards Siena. 

Given our mountaintop location in Volterra, our first stage of the day will be a long descent towards the Colle Val d’Elsa. We will then start to slowly climb once again through a nature reserve, before touring calmly along quiet country roads and through age-old villages over the undulating Tuscan landscape. 

Our destination on Day 3 is Siena, considered by many to be one of the most beautiful cities in Italy. We’ll have dinner out in the centre of this romantic, red-bricked city before taking a stroll around, giving us a chance to visit some of the local sites including the spectacular Duomo di Siena with its imposing Gothic exterior, and the Piazza del Campo.

Our route on Day 4 of our tour will take us through the very heart of Tuscany, with some of the most well-known beautiful scenery in the world. 

It is a comfortable stage riding over the undulating countryside, dotted with charming old farms surrounded by olive groves and vineyards lined with cypress trees. We will stop in Asciano for lunch in the mediaeval town.

Today’s destination is Montepulciano, a charming hilltop town of Etruscan origin that shares its name with one of Tuscany’s most famous wines, the Vino Nobile di Montepulciano. We’ll take some time in the afternoon to walk around downtown and sock up this historic location. 

Our route on Day 5 will take us out of Tuscany and into the region of Umbria, il cuore verde d’Italia (“the green heart of Italy”). We have a long ride ahead of us but it is a generally flat route. Our first stop will be at Lake Trasimeno, the largest lake in Central Italy, where we either have lunch or a coffee in one of the many bars beside the lake.

The next stage of our route will take us through the green and undulating landscape of Umbria, dotted with romantic mediaeval towns perched on hillsides and surrounded by luscious green countryside. One of these villages is Assisi, our final resting point, which we’ll see on the horizon 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 centre. We will have some free time in the afternoon to explore the city, before we sit down for a wonderful dinner and some delicious Umbrian wine after a long day in the saddle.

The route on Day 6 of our tour will be our first taste of mountain riding. Today we’ll enter the Apennines, a series of small (compared to some) mountain ranges that extend some 1,200 km from north to south straight through the heart of the Italian peninsula. Crossing these wild mountains is the only way to reach the Adriatic Sea if we want to complete a true coast-to-coast tour.

Our riding style changes today. After riding across rolling green hills for the first half of our trip, this stage offers a new challenge with long climbs at a moderate gradient, surrounded by breathtaking scenery. Our stopover for the night is the lovely town of Nursia, nestled inside the Monti Sibillini National Park at the foot of the Monti Sibillini.

Our route on Day 7 resembles an Alpine stage. We will leave Nursia in the morning and head out to ride on one of the most beautiful mountain roads in Umbria. Our first stop will be Castelluccio di Norcia that sits in the Piano Grande plateau at 1,452 m above sea level. It is a magical village surrounded by fields that bloom with intense colour each year between May and June.

We’ll take a road that leads us from the Valley of Nursia to the plateau, a long mountain road with a breathtaking view of the valley. Once we reach the plateau, we ride at altitude up to Castellucio.

The final stage of our route on Day 7 will be a long descent towards Camerino, where we will spend the night, at which point we cross over into Le Marche, the land of la dolce vita.

Le Marche is an almost untouched region of Italy that extends from the Apennines to the Adriatic Sea. It is not as well-known as its neighbours Tuscany and Umbria, but it is no less beautiful and offers a wealth of activities and beautiful sights to see.

Our route on Day 8 is another calm and peaceful ride through the Gola della Rossa e di Frasassi Regional Park, an extraordinary green landscape home to lakes, mountains and gorges. We will spend the night at a traditional farmhouse in Pergola, where we will have the chance to taste local organic food and wine and rest our legs after another long day in the saddle.

Day 9 is the penultimate day of our tour and the final leg of our journey by bike. As we move away from the mountains and towards the coast, our route returns to undulating terrain and green pastures.

This stage takes us from the heart of Le Marche to the glistening Adriatic Sea. Over the past eight days, we have crossed Italy from west to east through some of the most beautiful scenery the country has to offer. Take the afternoon to soak up this wonderful coastline and enjoy some delicious food and wine. When in Rome…!

Enjoy a final breakfast at our wonderful hotel beside the Adriatic Sea. We will also have some time in the morning to enjoy a final recovery ride around the local area before catching the transfer to Ancona airport or train station.