Road Cycling Tours in Tuscany

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Tuscany is one of the most famous regions in Italy, boasting culture, wine, breath taking views and above all, the best road cycling in Europe. Our cycling tours of Tuscany allow you to fully immerse yourself in the region by allowing you to take in these views, sample the local produce and live like a local for your time with us. Explore our fantastic cycling tours in Tuscany today to find your perfect adventure.

Guided

Italy

Tuscany - Giro della Toscana

Guided Road Bike Tour

Duration

8 days

Prices from

$2,995 P.P.

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Grade 3: Moderate

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Tuscany - Giro della Toscana

Guided Road Bike Tour

Start Date	End Date	Price p.p.
03/10/2026 Fully Booked	10/10/2026	$2,995.00
01/05/2027	08/05/2027	$3,135.00
29/05/2027	05/06/2027	$3,135.00
02/10/2027 Guaranteed	09/10/2027	$3,135.00

Cycling through the historic wine regions of Tuscany, stopping off for a bit of wine tasting along the way
Staying in quality accommodation, with fantastically warm hospitality
Easing along the rolling hills of the Colli Sienesi
Riding the stunning UNESCO heritage region of Val d’Orcia
Stopping off at the lovely San Gimignano and Montalcino
Chilling out with a post-ride Chianti

Photo Highlights Dates

Guided

Italy

Coast to Coast - L'Adriatico al Tirreno

Guided Road Bike Tour

Duration

9 days

Prices from

$4,035 P.P.

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Grade 3: Moderate

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Coast to Coast - L'Adriatico al Tirreno

Guided Road Bike Tour

Start Date	End Date	Price p.p.
22/05/2027	30/05/2027	$4,035.00
11/09/2027	19/09/2027	$4,035.00

An epic coast to coast journey riding all the way from the Adriatic coast to the Tyrrhenian Sea
Cycling through the smallest republic in Europe, San Marino
Easing along the rolling Nove Colli hills, the routes of the famous Italian Gran Fondo
Visiting historical sites such as the Palazzo Ducale in Orvieto and San Francis Abbey in Assisi
Staying in quality accommodation, with fantastically warm hospitality
Riding to Gubbio and Assisi, UNESCO World Heritage sites

Photo Highlights Dates

Self-Guided

Italy

Tuscany - Giro della Toscana

Self-Guided Road Bike Tour

Duration

8 days

Prices from

$2,565 P.P.

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Grade 3: Moderate

More Info BOOK NOW

Tuscany - Giro della Toscana

Self-Guided Road Bike Tour

Daily departures available. The season prices below are per person and are applicable for all start dates between and inclusive of the stated dates.

2026 29 Mar – 26 Oct (excluding dates in July and August)

Season 1 – $2565 29 Mar – 14 Jun and 09 Sep – 26 Oct

Season 2 – $2995 15 – 30 Jun and 01 – 08 Sep

2027 30 Mar – 26 Oct (excluding dates in July and August)

Season 1 – $2695 30 Mar – 14 Jun and 09 Sep – 26 Oct

Season 2 – $3135 15 – 30 Jun and 01 – 08 Sep

To ensure you have the best experience possible, we’d recommend travelling in the Spring or in the Autumn. We don’t as standard offer this tour in the hotter, more humid, busier summer months of July and August. If however your dates are set in July or August, please call us for a chat and we’ll do what we can to accommodate you.

Cycling through the historic wine regions of Tuscany, stopping off for a bit of wine tasting along the way
Staying in quality accommodation, with fantastically warm hospitality
Easing along the rolling hills of the ‘Colli Sienesi’
Riding the stunning UNESCO heritage region of Val d’Orcia
Stopping off at the lovely San Gimignano and Montalcino
Chilling out with a post-ride Chianti

Photo Highlights Dates

Not sure which trip's right for you? Just ask!

Get in touch and we'll help you find your perfect trip.

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Road Cycling Tours in Tuscany

2026

2027

2028

2026

2027

2028

Guided Road Bike Tour

Duration

Prices from

Guided Road Bike Tour

Guided Road Bike Tour

Duration

Prices from

Guided Road Bike Tour

Self-Guided Road Bike Tour

Duration

Prices from

Self-Guided Road Bike Tour

Not sure which trip's right for you? Just ask!

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