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TRIP CALENDAR

Eat up the miles, drink in the culture, with the greatest cycling trips in the world. Browse by season and destination to find the trip that fits your calendar, whether you’re chasing the Spring Classics, rolling into a Grand Tour stage town, or settling into a self-guided week through wine country.

Tuscany
Closed

Tuscany with David Arthur (Just Ride Bikes)

$7,450
5 Apr 2026

-

11 Apr 2026
This is our classic Tuscany trip, the culmination of all our local knowledge and a perfect expression of the Mangia, Beve, Bici experience. Back when he was still a professional cyclist, our …
Giorgio Valvassori
Tuscany
Closed
Special Edition

A Tuscan Trip for the Body and Soul

$7,950
26 Apr 2026

-

2 May 2026
If you’re looking for a cycling trip with a strong mind/body connection, join us for a week of meditation, yoga, ice baths, and of course, cycling. Based around our ever-popular …
Sancho da Cruz
Tuscany
Available

Chianti Classico

$7,450
13 Sep 2026

-

19 Sep 2026
This is our classic Tuscany trip, the culmination of all our local knowledge and a perfect expression of the Mangia, Beve, Bici experience. Back when he was still a professional cyclist, our …
Giorgio Valvassori
Tuscany
Sold Out
Best Seller

Chianti Classico

$7,450
27 Sep 2026

-

3 Oct 2026
This is our classic Tuscany trip, the culmination of all our local knowledge and a perfect expression of the Mangia, Beve, Bici experience. Back when he was still a professional cyclist, our …
Giorgio Valvassori
Tuscany
Sold Out

WHITE ROADS GRAVEL ADVENTURE

$7,450
4 Oct 2026

-

10 Oct 2026
Riders have been grinding gravel in Tuscany long before it became fashionable elsewhere. The region’s dusty backroads give an alternative view on this beautiful part of the world, and offer …
Giorgio Valvassori, Sancho da Cruz
Italy, Tuscany
Available
Special Edition

Women's Week: Tuscany in the Fall

$7,450
11 Oct 2026

-

17 Oct 2026
This is our women’s-only Tuscany trip, and everything that makes this journey so special — the riding, the food, the wine, the people — is experienced exclusively in the company …
Giorgio Valvassori
Italy, Tuscany
Available
Last Spot

Special Edition: Partner Trip 2026

$7,450
18 Oct 2026

-

24 Oct 2026
Riders have been grinding gravel in Tuscany long before it became fashionable elsewhere. The region’s dusty backroads give an alternative view on this beautiful part of the world, and offer …
Giorgio Valvassori
Italy, Tuscany
Available
Special Edition

Tuscany with Francis Reynard

$7,450USD
1 Nov 2026

-

7 Nov 2026
A one-time collaboration in Chianti. Chef Franck Reynaud joins inGamba's own Tommi in the Borgolecchi kitchen for a week of riding, cooking, and eating built around the two of them.
Giorgio Valvassori, Sancho da Cruz
Italy, Tuscany
Available
Best Seller

Strade Bianche 2027

$7,750USD
2 Mar 2027

-

8 Mar 2027
Riders have been grinding gravel in Tuscany long before it became fashionable elsewhere. The region’s dusty backroads give an alternative view on this beautiful part of the world, and offer …
Giorgio Valvassori
Tuscany
Available

Tuscany Classico

$5,950USD
21 Mar 2027

-

27 Mar 2027
Discover Tuscany by bike with inGamba. A luxury guided cycling holiday through Chianti Classico, led by former WorldTour professionals.
Giorgio Valvassori, Sancho da Cruz
Tuscany
Available

Tuscany Gravel

$7,850USD
4 Apr 2027

-

10 Apr 2027
Tuscany's famous white roads: chalky dirt tracks connecting medieval hilltop villages, winding through olive groves, and disappearing into tunnels of cypress. Expect loose, dusty switchbacks that demand real bike handling …
Giorgio Valvassori, Sancho da Cruz
Italy, Tuscany
Available
Special Edition

Tuscany Wellness Week

$9,650USD
10 Apr 2027

-

18 Apr 2027
Most cyclists know how to train the body. Fewer have learned to train the mind alongside it. This nine-day program is a collaboration between inGamba and Patrick Sweeney, a meditation …
Giorgio Valvassori, Sancho da Cruz
Tuscany
Available

Tuscany Classico

$7,850USD
2 May 2027

-

8 May 2027
Discover Tuscany by bike with inGamba. A luxury guided cycling holiday through Chianti Classico, led by former WorldTour professionals.
Giorgio Valvassori, Sancho da Cruz
Tuscany
Available

Tuscany Classico

$7,850USD
16 May 2027

-

22 May 2027
Discover Tuscany by bike with inGamba. A luxury guided cycling holiday through Chianti Classico, led by former WorldTour professionals.
Giorgio Valvassori, Sancho da Cruz
Tuscany
Available

Tuscany Classico

$7,850USD
23 May 2027

-

29 May 2027
Discover Tuscany by bike with inGamba. A luxury guided cycling holiday through Chianti Classico, led by former WorldTour professionals.
Giorgio Valvassori, Sancho da Cruz
Tuscany
Available

Tuscany Classico

$7,850USD
30 May 2027

-

5 Jun 2027
Discover Tuscany by bike with inGamba. A luxury guided cycling holiday through Chianti Classico, led by former WorldTour professionals.
Giorgio Valvassori, Sancho da Cruz
Tuscany
Available

Tuscany Classico

$7,850USD
5 Sep 2027

-

11 Sep 2027
Discover Tuscany by bike with inGamba. A luxury guided cycling holiday through Chianti Classico, led by former WorldTour professionals.
Giorgio Valvassori, Sancho da Cruz
Tuscany
Available

Tuscany Classico

$7,850USD
12 Sep 2027

-

18 Sep 2027
Discover Tuscany by bike with inGamba. A luxury guided cycling holiday through Chianti Classico, led by former WorldTour professionals.
Giorgio Valvassori, Sancho da Cruz
Tuscany
Available

Tuscany Classico

$7,850USD
19 Sep 2027

-

25 Sep 2027
Discover Tuscany by bike with inGamba. A luxury guided cycling holiday through Chianti Classico, led by former WorldTour professionals.
Giorgio Valvassori, Sancho da Cruz
Tuscany
Available

Tuscany Classico

$7,850USD
26 Sep 2027

-

2 Oct 2027
Discover Tuscany by bike with inGamba. A luxury guided cycling holiday through Chianti Classico, led by former WorldTour professionals.
Giorgio Valvassori, Sancho da Cruz

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