Tuscany Wine & Bike Tour

When you arrive in Florence, you can settle into your hotel and ease into the city’s pace. You can wander the historic centre, where the great dome of the Duomo rises above terracotta-roofed lanes and the Renaissance spirit still whispers through cobbled streets and artisan workshops. In the evening, you will enjoy a pre-booked dinner featuring regional dishes, paired with a well-selected Tuscan wine. The blend of old-town architecture, the hint of vineyards beyond the hills, and the quiet promise of the cycling days ahead will make it a fitting first night of your tour.

On your first cycling day out of Florence, you will move into the rolling vineyard hills of the Chianti region. You will leave the city behind and ride through Grassina, with its quiet lanes branching off from the suburbs into olive groves and wine country. Soon, you will arrive at San Polo in Chianti, where the path deepens into soft slopes between classic Tuscan farmhouses. You will then continue climbing gently into higher ground where the panorama opens out over sweeping vineyards, before traversing a ridge-line to your destination, the village of Greve in Chianti.

You will depart from Greve in Chianti and follow silence-draped side-roads that climb steadily through olive groves and vine terraces toward Casole and Lamole. As the asphalt gives way to gravel, the terrain will deepen its texture and lead you into the old-world village of Volpaia, perched high and quiet. From there, you will begin a sweeping descent toward Radda in Chianti, vineyards reclining beneath your wheels, and finish the day in Castellina in Chianti, where you will enjoy an evening wine tasting, sampling the region’s distinguished Chianti Classico wines in a cellar amid classic Tuscan countryside.

You will depart from Castellina in Chianti on a quiet route that skirts the outer slopes of the region, passing near Castelnuovo Berardenga, before extending into increasingly open countryside. The road surface will vary between asphalt and gravel, offering a textured experience as you move away from vineyard-lined ridges into broader expanses of Tuscan land. As you ride on, the setting will change: olive groves will give way to gentle hillscapes, soft light will settle on fields stretching toward Asciano in the Crete Senesi.

From Asciano, you will head towards the celebrated valley of Val d’Orcia, entering the rolling hills via San Giovanni d’Asso. Then you will ride into the vicinity of Pienza and San Quirico d’Orcia, two historic villages nestled amidst cypress-lined slopes and open farmland, before turning onto rustic lanes that lead you toward your day’s end in Montalcino, the heart of the region’s Brunello wine culture. Because of the significant elevation gain and extended distance, you can opt for a shorter way into Montalcino to be there in time for the evening wine tasting.

From your base in Montalcino, you will descend steeply toward Buonconvento, where you’ll briefly join a main road before turning onto quieter side lanes. From there, you will ride through the soft, chalky contours of the Crete Senesi—a landscape marked by its pale clay hills and spaced-out farmhouses, arriving at Chiusure. You will continue through the rural stretch of Vescovado and the valley of the Arbia, where the road surface softens and traffic thins. The day ends as you reach the historic city of Siena, with its medieval streets and unmistakable skyline.

On your departure day from Siena, you will enjoy a relaxed morning in the city, perhaps lingering a little longer over coffee in the famous Piazza del Campo or taking a quiet stroll through the medieval lanes. Later, you will transfer from Siena, leaving the timeless Tuscan landscape behind—though the memory of its rolling hills, vineyard-dotted countryside, and limestone roads will linger long after you’ve bowed out of this section of the tour.