Day 1 | Arrival Day 

Make your way to Cortona and settle in to your first night in a typically Tuscan hotel, with great food and wine on offer. Get a good night’s sleep, ready to ride on day 2. 

Day 2 | Optional Round Trip: Lake Trasimeno – In Hannibal’s Footsteps | Approx. 44km 

Our local team will meet you in the morning to get you set up on your e-bikes and talk you through the plan for your tour before seeing you off on your first-round trip ride. The route today heads east into the Val di Pierle, before climbing and descending into the Niccone valley. This valley, now a peaceful, agricultural area, has frequently served as a frontier throughout history – often between warring parties. You’ll pass the dramatic Pierle Castle on your descent, one of the many fortifications throughout the length of the valley. From here, another twisting climb opens up to a spectacular viewpoint of the lake at Gosparini. The ride finishes passing through Tuoro-sul-Trasimeno, famous as the site of Hannibal’s battle with the Romans in 217 BC, before returning towards Cortona. 

Day 3 | Cortona to Southern Chianti | Approx. 66km 

It’s time to head into the heart of Tuscany and today’s ride through the Val di Chiana, famed for its beef farming tradition, and into the southern edge of Chianti country is a beautiful way to experience it. Heading west, the ride passes through the lovely hilltop town of Lucignano early on, known for its flower festival that takes place each May. Continue riding on amidst stunning scenery to reach Asciano, which was once an Etruscan settlement and where there is a beautiful 11th-century church.  Stop here for refreshments at a pavement cafe in town before undertaking the final 15km of the day which will bring you through the famous lunar-esque landscape of the ‘Crete Senesi’, the Siena Clays. 

Day 4 | Optional Round Trip: Siena | Approx. 46km 

You have the freedom to take a rest day today, but for those looking to ride, we can propose a loop in and out of the world-famous and utterly beautiful town of Siena. Perched atop a hill and crowned by the tower of the grand Piazza del Campo, it is one of the region's most popular destinations and is well worth a visit. For those looking to take it easy, you could always ask the hotel to call a taxi to take you there – we won’t tell anybody! 

Day 5 | Cycle Southern Chianti to San Quirico d’Orcia | Approx. 49km 

Today's ride takes you south, partly following the ancient pilgrims' trail of the Via Franicgena. A lot of today’s riding takes place on the region's famous chalk roads, known locally as Strade Bianche. For cycling fans, these will conjure images of the Eroica, a vintage bike event that takes place on these roads each year. Crossing the river at Ponte d’Arbia you will find yourself in the charming village of Buonconvento, encircled by its 14th-century town walls. Stop off for lunch in the historic main street, Via Soccini. As you set off for the last few kilometres of your journey today, enjoy beautiful views of the distant Monte Amiata, the largest of the now dormant lava domes in the area.

Day 6 | Optional Round Trip: Montalcino | Approx. 40km 

Today is another day where you can take a break from cycling if you’d prefer. If you’d rather keep your legs turning, the nearby wine town of Montalcino makes for a great destination and we have an “out and back” route to take you there. Enjoy a lunch break with a glass of their local wine in this charming town, a less touristic counterpoint to Montepulciano which you’ll get to visit tomorrow. 

Day 7 | Cycle San Quirico d’Orcia to Cortona |Approx. 60km 

Your final day of riding sees you returning to the Cortona region, with plenty to see and do along the way. Today’s route takes you through some more of Tuscany’s jewels – including Pienza and the world-renowned wine town of Montepulciano – our preferred spot for lunch. After refuelling here, and taking some time to explore its streets, the route descends back into the Chiana Valley and follows a relatively flat route back to the doors of your last hotel of the trip. Enjoy a final night of Tuscan hospitality and raise a glass to a week of wonderful cycling. 

Day 8 | Departure Day 

After a final breakfast, we say arriverderci! 

Trip extensions and extra nights in Rome, Florence or Pisa are available on request.