Tuscany Immersion: Lucca to Siena | Lucca Cycling Club

Tuscany Immersion: Lucca to Siena

You know what the inside of your office looks like. You've put in your time. There's nothing else you should be doing.

In fact, there's no better way to kill productivity and joy than working too much. To create meaningful outputs in life, you've got to set your sights on KPIs that matter. Athletic pursuits that move the needle and stories that bring out the best in you, your friends and family.

Remember that person who did nothing? Neither does anyone else.

That's why my brand new Lucca to Siena point-to-point ride is required riding. It's 150 kilometers with 2300 meters of elevation, starting from Lucca's historic wall and finishing in Siena's Piazza del Campo.

There's something magical about escaping our usual habits and patterns to venture out into the unknown. It's why I've dedicated my professional career to creating experiences that challenge us to think and see differently.

When you have a destination — with 100% commitment — you have a mission. And embracing our missions in life empowers us to fulfill our uniquely human potential:

Until one is committed, there is hesitancy, the chance to draw back, always ineffectiveness. Concerning all acts of initiative (and creation), there is one elementary truth, the ignorance of which kills countless ideas and splendid plans: that the moment one definitely commits oneself, then Providence moves too. All sorts of things occur to help one that would never otherwise have occurred. A whole stream of events issues from the decision, raising in one's favour all manner of unforeseen incidents and meetings and material assistance, which no man could have dreamt would have come his way.

— William Hutchison Murray, Scottish mountaineer and writer

Ready to let Tuscany wash over you? Andiamo.

To get a head start, leave bright and early — before sunrise — and you'll escape the commuter traffic along with the summer heat in July and August. Anytime between 5:30 and 6:00 am. These hours of the day normally don't apply to me, but trust me, it's well worth it.

Male and female cyclist riding past a brick wall.
A man's red cycling shoes with green socks.
Two standing cyclists with bikes viewing the Tuscan sunrise.

I've tinkered and tested various routes, yet I always return to the mystical Pisan hills beyond Pontedera. Overlooked by most, these lands from the Lucchesia to Chianti are splendidly still and unfrequented.

No matter what you've been through or are going through, your ability to sense and recognize beauty is how you know everything will be okay. This is the effect of Pisan fog-filled hills at sunrise. Take it all in — I guarantee you'll get everything and much more than what you came for.

A female cyclist wearing a white helmet pointing at the hillside.
A male and female cyclist riding road bikes up a white gravel road in Tuscany.
Two cyclists riding between colorful buildings in Ghizzano.

If you happen to know of Ghizzano, it's likely for the wine. Yet, what I love about this small village is the public art surrounding Via di Mezzo where the building facades are painted in captivating shades of bright green and burgundy.

One of the biggest draws to bike-riding is the freedom to stray from the beaten path. The point isn't to follow the crowd but to discover what Viktor Frankl calls the space between stimulus and response. "In that space is our power to choose our response. In our response lies our growth and our freedom."

Brown colored Tuscan scenery with two cyclists in the far distance.
Brown colored Tuscan countryside and a meandering road with two cyclists in the distance.
Two cyclists descending a white gravel road in Tuscany.

Put yourself into different places and spaces and you'll start to understand just how far you've come. Pick a destination and follow a path and you'll see just how far you can go. Our greatest power is the freedom to choose.

If there are five major moves to make any ambitious dream come true, then you won't reach Siena without first passing through Casole d'Elsa. Once a historic Etruscan settlement, Casole d'Elsa is a hilltop village with stunning views of the Sienese countryside.

Two cyclists riding through the pedestrian alley in Casole d'Elsa.
A male cyclist filling up his water bottle at a water fountain in Casole d'Elsa.
Two road bikes leaning against a stone building in Casole d'Elsa.

It's small enough to escape mass tourism and big enough to enjoy a quality cappuccino, cornetto or even lunch. From Casole d'Elsa, there are only two climbs left to Siena; well, three according to the profile-but the first one doesn't count.

Just when you least expect it-and when you know you've made it-Siena appears in the distance. The crest of Via Santa Caterina (or the Strade Bianche Eroica Pro finish) is cue that you've arrived at your destination: Piazza del Campo.

Two cyclists riding up a steep climb in the historic center of Volterra.
Two cyclists sitting in Siena's Piazza del Campo with two bikes.
A male and female cyclist sitting in Siena's Piazza del Campo with two bikes.

If you care about who you are and what you contribute to this world, THIS ride is for you. To offer joy, we must first generate it within ourselves and what better place to top up your emotional bank account than Tuscany?

In this fully immersive experience with me, you'll see:

  • The Pisan hills at sunrise
  • Public art of Ghizzano
  • Jaw-dropping vistas
  • Volterra, Casole d'Elsa and Siena
  • 150 kilometers of Tuscan splendor

It would be my honor to guide you on this mission. If you're ready to immerse yourself in Tuscany and take on the challenge, book this ride here.

Note: While there is only one 1.5-kilometer gravel sector on this course, we recommend at least 28 mm tires, compact gearing, and 11/32 cassette.

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