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Tuscany Donkey Week


This is Donkey Week: inGamba, but not as most people ever get to know it. It’s Chianti cranked up to 11. More miles, more gravel, more wine, more trash talk. It’s probably not your average tourist’s idea of a cycling holiday. Donkeys need a strong liver, a thick skin and a good sense of humour.

The Italians like to say “Chi nasce asino non può morire cavallo.” And they’re right. If you’re born a donkey, you can’t die a horse. There’s no hiding what you are or trying to change into something else. Donkey Week is what it is. Hard, fast, full of laughter and late nights and wine and tomorrow’s memories. Maybe that’s not for everyone. But if you’re a donkey, you wouldn’t have Chianti any other way.

Colin O’Brien explains what is a donkey – check out his article here. 

Included With Trip:

  • All lodging*
  • All food and beverages**
  • Pinarello Dogma F10 bike rental with SRAM RED eTap 11-speed WiFLi components and daily bike wash
  • One Giordana FRc custom inGamba cycling kit and one additional Giordana FRc Inline cycling kit
  • Daily post-ride massage from a professional soigneur
  • Laundry service for cycling clothing


*Pre/post-trip lodging is not included

**Beverages ordered by guests beyond normal amounts and away from group activities will incur additional charges

Trip at a Glance

Start Location:


Finish Location:


Days Riding:


Group Size:

8 – 12

Total Distance:


Total Elevation:


Longest Day:

Day 3. Monte Amiata. 226km

Biggest Climbing Day:

Day 3. Monte Amiata. 4,300m


Day by Day Breakdown


Monti – Montelucco

Donkey Week returns to Chianti after a year away, and we are so happy to bring it back with seven new routes designed by none other than Jered Gruber. As the late afternoon light gives a glow to the hill-sides and the shadows lengthen, we will roll along ridgetops, through small villages where people sit outside to talk to one another and wave as you go by, and around the stout olive trees that blanket these fertile hillsides. This ride has one long, staircase climb up Monteluco that should shake out any cobwebs built up during your flight.

Dudda North

The standard Dudda loop is a firm favorite, but we’re mixing it up this time after taking some advice from map nerd and photographer extraordinaire, our friend Jered Gruber. For a new twist, we’ll reverse the course and send you straight up the Albola climb – an ascent Jered calls “Dudda on Drugs.” After our normal coffee stop, we’ll continue north before returning to what you may recognize as part of our old Cavriglia route. For dinner, we’re off to Castello di Ama to view the new installations before having dinner in their Ristoro.

Monte Amiata

When you look south from the ridgetops around inGamba HQ, you can usually see Montalcino, and sometimes in the distance you can see another, even larger peak. That is Monte Amiata, and it is a long way from Lecchi. Today we will tackle it. If it turns out to be too big a day we can cut it short to 155km. Time will be tight, but we do have to stop to see the Abbey of Sant’Antimo, regarded as one of the most beautiful abbeys anywhere in Europe and rumored to have been founded by Charlemagne.

Castellina Northwest

About half of this route will be familiar to our regular Donkeys. The rest, however, is new. We'll ride north from Castellina to the Val d’Elsa and some sinuous descents and after rolling through the industrial town of Poggibonsi, we'll ascend a good climb up to Castellina. Today finishes with the classic roads of the Castellina route into Ponte a Bozone and through Pianella up the valley to the final Lecchi climb.


Our ride today is again a twist on an old favorite, Panzano. However, this route takes a different descent to the north, thanks to another suggestion from Mr. Gruber. The 2016 Giro d’Italia’s individual TT ends in Greve in the piazza, so we’ll stop to check it out and grab a quick coffee before hitting the dirt road through Lamole to Volpaia, which features on the 75km l’Eroica course. We know that no self-respecting Donkey would ever choose that short option, so this is your chance to see one of the event’s most beautiful stretches without the shame of taking the easy way.


This is some seriously uncharted territory for inGamba. The valley to the east of Lecchi is the Valdarno and carries the River Arno through Florence and out to the Ligurian Sea. On the east side of this valley are some of the most beautiful roads in Tuscany.

Badia a Coltibuono

The Badia a Coltibuono ride always reminds us how lucky we are to be able to ride here. Named after an abbey founded in 1051 by the patron saint San Giovanni Gualberto. After an enjoyable 7km climb to Badia a Coltibuono, there’s a rhythmic descent to Radda as a reward for your efforts. After a light lunch at Borgolecchi we will have a 90 minute transfer to Florence to end our trip.