Cycle Tuscany & Chianti

Buongiorno! Welcome to Italy. Your adventure begins in Florence with a welcome meeting at 6 pm. The trip spends very little time in Florence, so it’s strongly recommended that you arrive a few days early if you want to experience all that this amazing city has to offer. If you do arrive early, maybe take a stroll around the historic Florence Cathedral or visit the Uffizi Gallery, Ponte Vecchio and the Piazzale Michelangelo. After your meeting tonight, consider heading out with your new group and local leader and hunt down some excellent pizza, your favourite Italian wine or a plate of bistecca alla Fiorentina (grilled steak cooked on the bone).

After breakfast this morning, take a private transfer to Radda in Chianti, where your cycling adventure officially begins. Relax with a coffee, then you’ll have a bike fitting. After, it’s time to take to the regional roads and wind your way through the countryside of the acclaimed Chianti wine region. Stop for lunch in Gaiole, then continue to the 12th-century Castello di Brolio. Next, visit the Casa Eroica – a multimedia museum focused on L'Eroica, a cycling movement dedicated to riding vintage bikes on gravel roads. After, jump back on your bike and cycle through the green hills that lead to the medieval city of Siena. Built across three hills, the city’s three major streets connect in a valley at the sloping Piazza del Campo. According to Roman mythology, Siena was founded by Senio and Ascanio, the twin sons of Remus. Tonight, why not seek out some local specialties for dinner – pici is a popular Sienese pasta shape (similar to spaghetti, but thicker) and is typically served with either wild boar ragu or a simple tomato sauce.

Cycle through the rolling Tuscan countryside as you head out of Siena towards Taverne d'Arbia. Take in views of the striking Crete Senesi region as you ride – from the saddle, you have a unique viewpoint from which you can see the spectacular colours transforming from green to orange, grey and brown. Follow the ancient Via Lauretana towards Asciano, winding through the white clay dunes (known as ‘biancane’), cypress trees and farmland. You’ll also traverse part of the Strade Bianche – the white gravel roads that form the cycling race of the same name. Arrive in the medieval town of Asciano in time for lunch. Explore the winding streets of this walled town on an orientation walk with your leader, then hop back on your bike to cycle back to Siena. The afternoon is free for you to explore Siena at your own pace. Maybe visit the Duomo di Siena, people-watch with a drink in hand in the Piazza del Campo or climb the 400 steps that lead to the top of the Torre del Mangia for panoramic views of the city.

Say farewell to Siena and cycle north through the rolling countryside towards the medieval walled town of Monteriggioni. Built in the 13th century as a fortress to defend Siena against the city’s historic rival, Florence, this is one of Italy’s best-preserved medieval towns. Hop off your bike, have a coffee and explore the town on foot, then continue your ride to the Parco Fluviale Alta Val D’Elsa, home to the charming streams and waterfalls of the Elsa River. After wandering some of the nature trails and maybe spotting some of the local fish or birdlife, get back on the saddle and head to the clifftop town of Colle Val D'Elsa, AKA the ‘Bohemia of Italy’. This small town is a global centre of handmade crystal glassware, producing almost all of the handmade crystal in Italy and 15 per cent of the crystal in the world. Ride on to your final stop for the day – San Gimignano. This UNESCO World Heritage-listed medieval walled town is home to 14 tower houses that were built by wealthy patrician families and offer excellent views over the town. The afternoon is free for you to explore. Kick back at a cafe or try some of the world championship-winning gelato at Gelateria Dondoli.

Gear up for a rewarding day on the saddle. Leave San Gimignano early this morning and ride through the undulating Elsa Valley, passing vineyards and dense oak woods and following in the footsteps of pilgrims as you cycle along the white gravel roads of the Via Francigena – the ancient pilgrimage route from Canterbury to Rome. Stop for a coffee break in the small village of Gambassi Terme. Continue on to the hilltop hamlet of San Miniato, where your cycling ends for the day. Have some lunch and join your leader on an orientation walk through town, where you’ll see buildings dating back to the 13th century. Take in panoramic views over the lower Arno Valley from town, then board a private vehicle for the drive to Lucca. The rest of your afternoon and evening are free. Ask your leader for recommendations on where to start exploring or simply relax – you have a full free day to explore laid back Lucca tomorrow.

Today is a free day off the bike in Lucca. Take the opportunity to see all the sights this city has to offer – maybe wander the former Roman amphitheatre off Via Fillungo and visit the medieval houses now standing in its place. Grab a seat at one of the Piazza dell'Anfiteatro's many outdoor cafes and watch the world go by with a coffee or glass of wine or stop by Foro Square and see the San Michele Church, which was built over the top of an ancient Roman forum. If you’re looking for the best spots to eat, your local leader will always have the best recommendations!

Leave Lucca by on your final bike ride this morning and follow the flat leafy bike paths downstream along the banks of the Serchio River to Pisa – home to the legendary leaning tower. After cycling through Pisa's bustling streets and taking your classic Pisa photo, maybe take some time to wander the shopping streets here or sip on an aperitif at one of Pisa’s many cafes and bars. Later, maybe head out for a final dinner with your group and indulge in a well-earned Italian feast one last time.