Our staff will meet you at Pisa International Airport and will accompany you to the Buonamico estate in Montecarlo. After a light lunch we‘ll be ready for our bike tune-up and a first warm up ride, also known as “sgambatella” in Italian slang, to prepare our legs for the days to come. From the Buonamico estate, we will cycle up and down the beautiful hills nearby Montecarlo, surrounded by age-old olive groves and vineyards. After the ride, we’ll open a bottle of the finest Buonamico wine and toast to the amazing week ahead.

Meals: Dinner

Cycling: distance 35 km, elevation 400 meters

Pick-up location: Pisa International Airport

Greet the day over breakfast, then we will get ready to pedal along beautiful routes past fabulous ancient villas before challenging ourselves with a gradual climb. Starting from Montecarlo we will cycle to one of Tuscany’s hidden gems, a town called Lucca, where we will enjoy riding on the ancient walls before cycling through the breathtaking medeival centre. The next location we will reach is Matraia where we will stop for an illuminating glimpse at its famous Roman-Catholic church and take some pictures. We’ll continue riding across the stunning countryside through olive groves and vineyards to Collodi, a village where small houses flow down a steep hill like a waterfall. From here we’ll ride back to Montecarlo, where we will stop for a coffee and enjoy a magical view of the valley.

Meals: Breakfast, Dinner

Cycling: distance 90 km, elevation 800 meters

After a rich Italian breakfast, we ‘ll be ready for our ride. We’ll guide you through the very nice rolling hills of Montecarlo heading towards the Monti Pisani, not too far from Lucca. Here we will face the ascent towards the Monte Serra. This is a serious climb, about 8 km long with an average gradient of 6%, that we will tackle at the right pace enjoying the wonderful landscapes we will pass through. Once on top, we will stop for a while to take pictures, have an espresso and enjoy the beautiful view of Pisa and its famous leaning tower. Then we’ll go down through Calci and Nozzano Castello. We will continue pedalling for another 20km before climbing the last gentle ascent 3,5 km long up to the wonderful Pieve S. Stefano which is immersed in ancient olive groves. Once back in Montecarlo, you will be able to relax and enjoy your last evening on the Buonamico estate.

Meals: Breakfast, Dinner

Cycling: distance 90 km, elevation 800 meters

This morning we’ll set off to our first destination, San Gimignano. The first part of our route is pretty flat before we take on some gentle slopes heading towards San Miniato, a town made famous for its wine and white truffles. We’ll stop for lunch and we’ll savour flavour local wines and taste the delicious white truffles that have made this town famous. After lunch we will approach the Val D’Elsa cycling along the Via Francigena that will take us to San Gimignano, a medieval town where we will admire the beautiful La Rocca di Montestaffoli and the Torre Grossa. You will have time to relax before being ready for a traditional dinner.

Meals: Breakfast, Dinner

Cycling: distance 85 km, elevation 1000 meters

We leave San Gimignano heading south, riding through the lush forest of the Natural reserve of Castelvecchio. After a number of rolling hills a long downhill will take us to the medieval town of Colle Val d’Elsa, widely known for its quality crystal production. From there we’ll ride on a quiet bike path traced along the former train route all the way to Poggibonsi. After lunch the road climbs gently toward the Chianti region. The oak trees leave place to the Sangiovese vineyards before reaching Castellina in Chianti. The last stretch extends between Castellina in Chianti, Radda in Chianti and our destination: the medieval fortified hamlet of Volpaia.

Meals: Breakfast, Dinner

Cycling: distance 85 km, elevation 1600 meters

Our exploration of Chianti begins with the northern area of this region. From Volpaia we’ll head towards Lucolena in Chianti and then make our way down to Strada in Chianti, a perfect lunch spot. After a hilly morning the afternoon is on more mellow terrain with only two major climbs. The first one will start right after Greve in Chianti and goes all the way to Panzano in Chianti: this climb is the perfect way to enjoy the views of the hills surrounding the charming hilltop town of Panzano. The second climb is the one going back to Volpaia. After the ride join us for a wine tasting in the property cellar.

Meals: Breakfast, Dinner

Cycling: distance 75 km, elevation 1400 meters

A day around the routes of l’Eroica. Get to experience the amazing scenery that made this event famous worldwide without giving away the comfort of asphalt roads. Today we’ll add Gaiole, the spectacular medieval hamlet to our collection of “in Chianti” towns. The route will also pass through the charming Castello di Brolio and the former convent of Badia Coldibuono, a medieval building perched on the top of a hill dominating the Valdarno valley.

Meals: Breakfast, Dinner

Cycling: distance 70 km, elevation 1550 meters

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

Meals: Breakfast

Drop-off: Florence or Pisa International Airport