Classic Tuscany Cycling Holiday: Florence, Siena & Pisa

Cradle of the Renaissance.

Arrive in Florence, the magnificent birthplace of the Renaissance, and enjoy the afternoon exploring the city at your own pace. Climb Giotto's Campanile for sweeping views across the terracotta rooftops, visit the masterpieces of the Uffizi Gallery, or wander across the historic Ponte Vecchio and through the atmospheric streets surrounding it.

Later in the afternoon, meet our local team for your personalised bike fitting and tour briefing. We'll also help you get set up with the digital route app and share some local recommendations for restaurants and places to eat, so you're ready to make the most of your time in Tuscany.

Into the Chianti Hills

Distance: 61 km | Elevation Gain: +1230m | Terrain: Hilly

Leave Florence behind and begin your first day of cycling with a series of rewarding climbs into the heart of Chianti. As the city gives way to rolling countryside, vineyards, olive groves and wooded hills, the landscape quickly becomes quintessentially Tuscan.

Stop in Greve in Chianti, the region's historic market town, and take time to explore its distinctive main square. Food lovers can visit the renowned Macelleria Falorni, a family-run butcher and delicatessen celebrated for its traditional Tuscan cured meats and other local specialties.

From Greve, continue deeper into the Chianti hills along quiet, vineyard-lined roads, with plenty of opportunities to pause and enjoy the scenery. Your destination is Radda in Chianti, a beautifully preserved medieval hill town and historic crossroads at the heart of the Chianti wine region.

Medieval Rivalries & Piazza del Campo.

Distance: 52 km | Elevation gain: +958 m | Terrain: Hilly.

Leave the heart of Chianti behind and continue south through quiet valleys, vineyards and wooded hills, with a series of rewarding climbs along the way. As the landscape opens up, you'll approach Siena, Florence's historic medieval rival and one of Tuscany's great cultural treasures.

Enter the city through its imposing historic gates and leave the bike behind as you step into Siena's beautifully preserved medieval centre. Spend the afternoon wandering its narrow stone streets, discovering atmospheric piazzas and historic buildings, or simply settle into a café for a coffee or gelato in the magnificent Piazza del Campo, the city's famous shell-shaped square and home of the legendary Palio horse race.

Walled Jewels and Medieval Towers.

Distance: 52km | Elevation gain: +895m | Terrain: Hilly.

Leave Siena behind and head into the heart of the Tuscan countryside, following quiet roads through rolling farmland, vineyards and elegant landscapes dotted with historic aristocratic villas.

Your first highlight is Monteriggioni, a wonderfully preserved medieval village enclosed by imposing stone walls and distinctive watchtowers. Take some time to wander through its atmospheric streets and enjoy the views before continuing through the countryside towards San Gimignano.

As you approach, the town's famous medieval towers rise above the surrounding hills, announcing your arrival at one of Tuscany's most celebrated historic centres. San Gimignano, a UNESCO World Heritage site, is renowned for its remarkable collection of 13th-century stone towers, medieval streets and beautifully preserved architecture.

The Genius of Leonardo & Agriturismo Stay.

Distance: 72km | Elevation Gain: +1021m | Terrain: Hilly.

Leave San Gimignano behind and ride through the rolling vineyard hills and peaceful countryside of Tuscany, passing through small rural hamlets and quiet lanes along the way.

Your destination is Vinci, birthplace of Leonardo da Vinci. Take time to explore the Leonardo Museum, where scale models bring his extraordinary designs and engineering ideas to life, before visiting the house where he is believed to have spent his childhood.

After a rewarding day on the bike, settle into the relaxed surroundings of an authentic Tuscan agriturismo, where you can unwind and enjoy the atmosphere of the countryside.

Distance: 59 km | Elevation gain: +438 m | Terrain: Rolling hills.

Leave Vinci and continue west through the peaceful Tuscan countryside, following quieter roads over gently rolling hills towards Lucca. Along the way, stop at Cerreto Guidi to climb the grand staircase of the Medici Villa, where you'll be rewarded with sweeping views across the surrounding valley.

Continue towards Lucca, a former Roman colony that grew into one of Tuscany's most prosperous medieval city-states. As you approach, the city's magnificent 17th-century defensive walls come into view, remarkably preserved and still encircling the historic centre.

Once inside the walls, take time to explore Lucca's elegant piazzas, cobbled streets and historic churches, or simply enjoy an evening stroll along the tree-lined ramparts.

The Leaning Tower, Puccini's Lake & Tyrrhenian Coast.

Distance options: 31 km (flat, return by train) | 61 km (flat loop) | 77 km (rolling loop) | +29 km (coastal extension).

Your final day offers a choice of routes, allowing you to tailor the riding to your energy and interests. Follow flat roads through the countryside to Lake Massaciuccoli, a peaceful wetland landscape closely associated with composer Giacomo Puccini, who found inspiration here while composing some of his best-known operas.

Continue to Pisa and make your way into the magnificent Piazza dei Miracoli, home to the city's world-famous Leaning Tower, cathedral and baptistery. Take time to explore the square and soak up the atmosphere before choosing how you'd like to return to Lucca.

For an easier option, board a local train with your bike for the journey back to Lucca, making this a 31 km cycling day. If you'd prefer more time in the saddle, choose the 61 km or 77 km loop routes, which take you back through scenic Tuscan countryside and rolling hills. Stronger riders can add a further 29 km coastal extension to reach the Tyrrhenian Sea.

Return to Lucca for your final evening and enjoy a leisurely passeggiata along the city's atmospheric pedestrian streets.