Val d'Orcia, Tuscany

Tuscany

[ OVERVIEW ]

Tuscany is cycling as art: cypress-lined climbs, hilltop towns glowing at sunset, and the famous strade bianche — the white gravel roads of the Chianti hills that host one of the most beautiful races in the sport. This journey rolls through the postcard landscapes of Siena, Val d’Orcia and Chianti with wine tastings, long Italian lunches, and a support vehicle never far behind.

Experience Details

Next Dates

TBC

Trip Duration

7 days, 6 nights

Pricing from

€4,899

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Overview of an Italian historic town with a tall clock tower, terracotta roofs, and a central plaza with people, against rolling green hills under a blue sky with some clouds.

White roads and golden hills through the cradle of the Renaissance

Ride Features

Punchy, rolling terrain in the country that gave the sport L’Eroica: famous strade bianche sectors like Monte Sante Marie — the white gravel roads where the modern Classic is decided each March, entirely rideable on a road bike with the right tyres — the SR222 through the heart of Chianti between Greve, Castellina and Radda, and quiet climbs to hilltop towns where the reward is an espresso in a square unchanged in five centuries.

Food & Drink

This is the region that invented the long lunch, and we plan rides around it. Brunello tastings in Montalcino, Vino Nobile in Montepulciano’s underground cellars, pecorino aged in the caves of Pienza, ribollita, and bistecca alla fiorentina done over oak. The best tables in the hill towns are small and book out — ours are reserved before you land.

Sightseeing & Culture

Siena’s shell-shaped Piazza del Campo and its cathedral, the towers of San Gimignano at dusk after the day-trippers leave, Vasari and Renaissance masters in the region’s quieter galleries, and the cypress-lined roads of the Val d’Orcia — the most photographed landscape in Italy, best seen at riding pace.

Accommodation

A 4-star countryside estate or restored borgo among the vines — pool, terrace, and views over the roads you rode that morning. Tuscany’s rural hotels understand hospitality at a level few regions match; we choose ones that also understand a bike is not luggage.