You will meet our guides at Pisa International Airport who will transfer you to your hotel in Lucca. This enchanting town is one of the prides of Tuscany. After a refreshing lunch, we’ll get fitted on our bikes and head off for a warm-up ride to get comfortable for the week ahead. From the centre of Lucca, in a few minutes we will reach some of the most beautiful hills in the area, surrounded by endless olive groves and vineyards. We’ll stop in one of the best-known local enotecas and with glass in hand we’ll toast to the week ahead. Back at the hotel we’ll get ready for a five-star dinner at one of the finest restaurants in town.

Meals: Dinner

Cycling: distance 35 km, elevation 400 meters

Pick-up location: Pisa International Airport

Our adventure is about to begin! We’ll initially ride along flat peaceful roads through miles of vineyards and olive groves. After the first 30 kilometres we’ll get to Cecina, famous for its cypress avenue. We’ll meet a series of ascents and descents which become more challenging once we get to Monte Scudaio. After an exhilarating descent we’ll pass through Montecatini Val di Cecina, where we’ll have a glimpse of the unique medieval Belforti Tower which sits on the top of a lush green hill, before lunch. We’ll continue cycling through green pastures and stunning farmland to Volterra, a charming hilltop walled town renowned for its peculiar urban layout that reminds us of its Etruscan origins. Then, off to our hotel where we will get ready to enjoy a professional post-ride massage before an unforgettable culinary experience.

Meals: Dinner

Cycling: distance 120 km, elevation 1.370 meters

Today we’ll start our ride pedalling along a stunning route which will consist of several series of challenging ascents and descents across the famous Chianti area, well-known both for its splendid wines and for its breath-taking landscape. We will venture along stunning paths reaching the famous villages of Castel S. Gimignano, Colle Val d’Elsa and Radda in Chianti where we’ll stop for a visit to a fine winery to sample its wine and other local delicacies. Back on our bikes, we’ll pedal along pastoral roads alongside endless vineyards and olive groves across the scenic green rolling countryside which will lead us to Siena, where we’ll have a gourmet dinner after a smoothing post-ride massage at our hotel.

Meals: Dinner

Cycling: distance 118 km, elevation 2.000 meters

After enjoying a relaxing breakfast we’ll gear-up to enjoy another stellar ride with scenic views of endless countryside passing through hilltop time-forgotten villages like Roccastrada and Civitella Paganico, from where we’ll enjoy a marvellous landscape that fades into the Ombrone Valley. In the territory of Civitella Paganico we’ll also find the famous Petriolo Hot Springs, with thermal baths that have been in use since antiquity. Along the way we will stop for a traditional lunch in one of our favourite local trattorias. We’ll cycle through the Basso Merse Natural Reserve, before getting to today’s final destination, Montalcino, where we’ll enjoy a rejuvenating post-ride massage at our hotel before a well-earned gourmet dinner.

Meals: Dinner

Cycling: distance 110 km, elevation 1.550 meters

This morning we’ll wind our way through the lovely little medieval villages that dot the hills. We’ll continue to work our way across the rolling stunning countryside passing through several small villages in the scenic Val D’Orcia such as Radicofani. For nature lovers the Fosso Bianco is a must see. It’s a stream in the woods at the confluence of several hot springs, where you can swim all year long. In the heart of Val D’Orcia there are lots of fantastic traditional trattorias where we’ll stop for a cyclist-friendly 🙂 lunch. Back on our bikes we’ll head to Cortona, a quintessentially Tuscan town to our hotel where we will have some time on our own and have a rejuvenating post-ride massage. After an aperitivo we will be ready for a delicious dinner.

Meals: Dinner

Cycling: distance 100 km, elevation 1.750 meters

Today we’ll pedal along dreamy roads through lush rolling hills punctuated by Etruscan villages, passing through Orvieto, one of the most memorable hilltop towns in central Italy, renowned for its magnificent cathedral and the Etruscan Temple of Belvedere. We’ll hop on our bikes again along the roads that Gino Bartali also rode to get to Assisi. We’ll meet three gradual climbs followed by flatland, across an untouched landscape in the heart of Umbria, where we will stop at one of our favourite eateries to enjoy local food and wine. We’ll continue our route along smooth roads across idyllic countryside to get to Assisi, one of the most beautiful towns in Italy, famous for its Basilica of San Francesco. In the afternoon you will have the chance to visit the most beautiful sights in town, before a professional post-ride massage and a unique five-star dinner.

Meals: Dinner

Cycling: distance 117 km, elevation 1.700 meters

After a delicious gourmet breakfast, an amazing morning ride will bring us to some of the most beautiful areas in Italy, passing the border between Umbria and Marche. This wonderful region is well-known for its picturesque landscape, which resembles a colourful canvas. We’ll pass through several quaint medieval villages like Gualdo Tadino, all rich in art and history, where we’ll stop for a wine tasting, and seize the opportunity to sample the local delicacies such as Ascolana olives and delicious white truffles. Our ride concludes with magnificent coastal vistas before reaching the lovely town of Ancona, where we’ll find the perfect blend of modern facilities and magnificent historical buildings. This evening we will celebrate the end of this fantastic adventure with a memorable dinner.

Meals: Dinner

Cycling: distance 119 km, elevation 1.500 meters

Our final breakfast is followed by goodbyes from our guides before they see you off to your next destination.

Meals: Breakfast

Drop-off: Ancona Airport or Bologna Airport or Pisa Airport