Tuscany

From Chianti Hills to Brunello Lands

Ride from the rolling hills of Chianti to the timeless landscapes of Val d’Orcia, crossing some of Tuscany’s most iconic wine territories. The route winds through vineyards, medieval villages, cypress-lined roads, and quiet countryside, revealing the deep connection between landscape and winemaking tradition. Along the way, discover renowned wines such as Chianti Classico and Brunello di Montalcino. A journey by bike through the authentic heart of rural Tuscany.
Total
distance		 Total
ascent		 Bike
excursion		 Bike
recommended
EXPERT
5 DAYS / 4 BIKE DAYS 		(240 KM / 155 ML) (3900 mt / 12800 ft) (3 - 4 h) Gravel & Road bike
CLASSIC
5 DAYS / 3 BIKE DAYS 		(150 Km / 95 Ml) (2500 mt / 8200 ft) (2 - 3 h) Gravel bike, Road bike & E-bike
LEISURE
5 DAYS / 3 BIKE DAYS 		(120 Km / 75 Ml) (2000 mt / 6500 ft) ( 2 - 3 h) E-bike
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From Chianti Hills to Brunello Lands

Tour details

Start: Chianti area

Finish: Val d'Orcia area

Wines:

Chianti Classico DOCG, Brunello di Montalcino DOCG, Rosso di Montalcino DOC, Orcia DOC

Where to stay

Day 1 – 2 – 3 Chianti area
(Barberino Val d’Elsa, Castellina in Chianti, Gaiole in Chianti, Radda in Chianti or Castelnuovo Berardenga area)
Day 4 – 5 Val d’Orcia area (Montalcino, San Quirico d’Orcia, Pienza area)

Best time to ride

March, April, May, June, September, October, November

Nearest airport

Reccomended arrival airport: Florence airport 1 h, Pisa airport 1h 30 min,
Reccomended departure airport: Florence airport 1 h 30 min, Pisa airport 2 h 30 min

✓ What's included

  • Expert Bike-Guide
  • Customized itineraries depending on the level selected
  • GPX tracks
  • Road Bikes, Gravel Bikes or E-bike
  • High-level mechanical support with bike fit upon arrival, daily bike maintenance and cleaning
  • Two Customized WINE RIDERS Cycling Kit
  • Water, bars, salts and Coffe breaks during the stage
  • Van to support and provided luggage service throughout the entire itinerary
  • Daily food and wine experience to selected wineries, local producers
  • Three typicals dinners included
  • Off Road wine tour in Chianti by Land Rover Defender

× What's not included

  • Hotel accommodation
  • Breakfasts, lunches, and dinners not included in the organized experiences
  • Travel insurance
  • Tips
  • Extra services on request
  • Anything not specifically mentioned under “Included”

Our itineraries include routes along secondary roads, mostly paved, with little traffic and set in open countryside.

The experiences we have selected will bring you into contact with the most authentic wineries in the region, including cellar visits and food & wine tastings.

Our team will be delighted to plan your vacation with you, whether you're a couple, a family, or a group of friends, for anywhere from a minimum of 2 to a maximum of 12 people. For further requests, do not hesitate to contact us

From Chianti Hills to Brunello Lands

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