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Cycling Tuscany: Chianti & Siena

From £1,095.00
8 Days & 7 Nights
Read 15 reviews

Cycling Tuscany: Chianti & Siena

  • Cycle the rolling Cypress tree lined Tuscan hills
  • Dine in the buzz of Piazza di Campo, Siena
  • Ride amongst the vineyards of Montepulciano
  • Poolside relaxtion 'Under a Tuscan Sun'
  • Sample the gelato of San Gimignano
Experience the very best of classic Tuscany on a self-guided cycle tour. Take to two wheels and cycle bella Italia, discovering picture-postcard Medieval and Renaissance hill-top villages, accompanied by sumptuous cuisine and the famed Chianti, Brunello and Nobile wines. Each day you will be cycling at your leisure through impossibly pretty scenery, characterised at first by vineyards and verdant farmland which lead to contrasting cypress-lined country roads, the UNESCO World Heritage Landscape-listed Val d’Orcadia and the grey hues of the ‘Crete’ region. Your Tuscan adventure starts with an incredible first day’s cycling; visit the fortified town of Monteriggioni, before heading to one of Italy’s most spell-binding locations—San Gimignano with its many towers. Each day you’ll reach traditional villages perched atop rolling hills filled with stunning red brick and earthen-coloured buildings, with roofs baked by the Tuscan sun. Highlights include magical Siena, the thermal-spa town of Bagno Vignoni and Pienza, as well as photogenic Montichiello and Montepulciano. Cool churches, abbeys and monasteries await you, where Gregorian chants drift through the air and create a special ambience. Take time to reflect at the Monte Oliveto monastery and peaceful abbey of Sant’ Antimo. You’ll also pass through towns located on the route of the ancient Via Francigena pilgrimage. And the end to each perfect day’s cycling? You’ll certainly have earned a glass or two of full-bodied Italian red accompanied by a dish garnished with local pecorino cheese and truffles! Tuscany is well known for its steep hills and therefore this trip will appeal to those with a good level of fitness, with daily distances ranging from 35 to 46 kilometres.


Day 1 Arrive Poggibonsi and overnight Day 2 Loop cycle to Monteriggioni, Colle Val d’Elsa and San Gimignano 22 miles / 35 km Day 3 Poggibonsi to Siena 20.5 miles / 33 km Day 4 Siena to ‘Crete’ to Buonconvento 25 miles / 39 km Day 5 Cycle to Monte Oliveto Monastery and Montalcino 29 miles / 46 km Day 6 Loop cycle to Sant’ Antimo Abbey 20 miles / 32 km Day 7 Cycle to Pienza, Montichiello and Montepulciano 28 miles / 45 km Day 8 Onward travel

This trip has a carbon score of 7kg per person per night, meaning it’s one of our best trips! For comparison, a carbon count of 7kg is equivalent to 1 single running shoe (not even a pair!). Here at Macs, we pride ourselves on being a responsible travel company and continue to adopt, develop and innovate ways to positively impact the environment. Find out more information on how we've carbon counted our trips.


Other Information

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Reasons to believe in Macs Adventure:
The Biggest Choice

The Biggest Choice

Self-guided walking & cycling is all we do - we have over 500 tried & tested trips.
Our Heritage

Around Since 2003

We’re still founder led & the world’s number one self-guided operator with mountains of experience.

21,000+ Customer Reviews

Plus, with a Feefo Platinum Service Award & British Travel Awards, you know you're in good hands.
Positive Impact

Positive Impact

We use independent suppliers to support communities along our routes, as well as work with organisations to help maintain & restore paths.
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