Tuscany Cycling Holidays & Tours

Grade 3 : Moderate

Tuscany - Giro della Toscana

Guided Road Cycling Holiday

Start Date	End Date	Price p.p.
29/08/2026 Contact Us	05/09/2026	£2,095.00
03/10/2026 Fully Booked	10/10/2026	£2,095.00
01/05/2027	08/05/2027	£2,195.00
29/05/2027	05/06/2027	£2,195.00
02/10/2027 Guaranteed	09/10/2027	£2,195.00

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

Guided

Italy

Tuscany to Rome

Guided Electric Bike Holiday

Duration

8 days

Prices from

£2,395 P.P.

Grade 3 : Moderate

Tuscany to Rome

Guided Electric Bike Holiday

E-BIKE HOLIDAY

This holiday has been designed as an e-bike tour allowing you to experience more on two wheels whilst riding with like-minded Skedaddlers. Confident cyclists will enjoy the boost from a battery for those cheeky climbs and longer distances. With less effort required on the bike, you’ll have more energy at the end of the day for off-the-bike activities. Remember to select your e-bike hire when you book your holiday with us.

Start Date	End Date	Price p.p.
12/09/2026 Last Spaces	19/09/2026	£2,395.00
08/05/2027	15/05/2027	£2,495.00
04/09/2027	11/09/2027	£2,495.00

Staying in Tuscan accommodation overlooking stunning landscapes
Discovering the amazing towns of Siena, San Quirico and Pienza
Sampling the best wines of Chianti, Montepulciano and Montalcino
Enjoying the journey from Tuscany to Rome on a variety of terrain, including ancient Roman roads
Exploring the lesser-known historical towns of Lazio, such as Sutri with it’s Roman amphitheatre
The sense of achievement riding into St Peter’s Square in Rome

Guided

Italy

Coast to Coast - L'Adriatico al Tirreno

Guided Road Cycling Holiday

Duration

9 days

Prices from

£2,695 P.P.

Grade 3 : Moderate

Coast to Coast - L'Adriatico al Tirreno

Guided Road Cycling Holiday

Start Date	End Date	Price p.p.
12/09/2026 Last Spaces	20/09/2026	£2,695.00
22/05/2027	30/05/2027	£2,825.00
11/09/2027	19/09/2027	£2,825.00

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

Guided

Italy

Tuscany - Strade Bianche Explorer

Guided Gravel Riding Holiday

Duration

8 days

Prices from

£2,225 P.P.

Grade 3-4 : Moderate/Challenging

Tuscany - Strade Bianche Explorer

Guided Gravel Riding Holiday

Start Date	End Date	Price p.p.
20/09/2026 Last Spaces	27/09/2026	£2,225.00
24/04/2027	01/05/2027	£2,295.00
08/05/2027	15/05/2027	£2,295.00
25/09/2027	02/10/2027	£2,295.00

Riding some of the classic Tuscany gravel routes including the Strade Bianche
Cycling through the historic wine regions of Tuscany, stopping off for a bit of wine tasting
Exploring the region on a mix of terrains
Riding the stunning UNESCO heritage region of Val d’Orcia
Relaxing in small villages for a coffee with the locals
Easing along the rolling hills of the ‘Colli Sienesi’
Chilling out with a post-ride Chianti or Brunello

Self-Guided

Italy

Tuscany - Giro della Toscana

Self-Guided Road Cycling Holiday

Duration

8 days

Prices from

£1,795 P.P.

Grade 3 : Moderate

Tuscany - Giro della Toscana

Self-Guided Road Cycling Holiday

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 – £1795 29 Mar – 14 Jun and 09 Sep – 26 Oct

Season 2 – £2095 15 Jun – 30 Jun and 01 – 08 Sep

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

Season 1 – £1885 30 Mar – 14 Jun and 09 Sep – 26 Oct

Season 2 – £2195 15 Jun – 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

Self-Guided

Italy

Strade Bianche Explorer

Self-Guided Gravel Riding Holiday

Duration

8 days

Prices from

£1,895 P.P.

Grade 3-4 : Moderate/Challenging

Strade Bianche Explorer

Self-Guided Gravel Riding Holiday

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 throughout July and August)

Season 1 – £1895 29 Mar – 14 Jun and 09 Sep – 26 Oct

Season 2 – £2095 15 Jun – 30 Jun and 01 – 08 Sep

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

Season 1 – £1995 30 Mar – 14 Jun and 09 Sep – 26 Oct

Season 2 – £2195 15 Jun – 30 Jun and 01 – 08 Sep

Riding some of the classic Strade Bianche route of Tuscany as well as lesser-known gravel routes
Cycling through the historic wine regions of Tuscany, stopping off for a bit of wine tasting
Exploring the region on a mix of terrains
Riding the stunning UNESCO heritage region of Val d’Orcia
Relaxing in small villages for a coffee with the locals
Easing along the rolling hills of the ‘Colli Senesi’
Chilling out with a post-ride Chianti or Brunello

Self-Guided

Italy

Tuscany - Sacred Routes

Self-Guided Mountain Bike Holiday

Duration

8 days

Prices from

£1,795 P.P.

Grade 3 - 4: Moderate/ Challenging

Tuscany - Sacred Routes

Self-Guided Mountain Bike Holiday

E-MTB HIRE AVAILABLE

This holiday is great fun on a regular mountain bike or an e-mountain bike and you can choose to hire either when you book your holiday with us! If you’re an experienced rider, you can choose one of our quality e-mountain hire bikes and experience the buzz of a pedal-assisted ride. Select your e-MTB hire when you book a holiday with us. Bear in mind that the pace will be set to riders with a regular mountain bike.

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 throughout July and August)

Season 1 – £1795 29 Mar – 14 Jun and 09 Sep – 26 Oct

Season 2 – £1995 15 – 30 Jun and 01 – 08 Sep

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

Season 1 – £1885 30 Mar – 14 Jun and 09 Sep – 26 Oct

Season 2 – £2095 15 – 30 Jun and 01 – 08 Sep

Staying in lovely Tuscan accommodation overlooking stunning landscapes
Riding the Montagnola trails, the location of a well-known Sienese MTB race
Sampling the best wines of Chianti, Montepulciano and Montalcino
Riding down the “Crete Senesi” on a roller coaster ridge ride
Enjoying the journey across Tuscany on a variety of terrain
Visiting the famous hilltop towns of San Gimignano, Monteriggioni, San Quirico d‘Orcia and Pienza

Guided

Italy

Tuscany - Sacred Routes

Guided Mountain Bike Holiday

Duration

7 days

Prices from

£2,195 P.P.

Grade 3 - 4: Moderate/ Challenging

Tuscany - Sacred Routes

Guided Mountain Bike Holiday

E-MTB HIRE AVAILABLE

Start Date	End Date	Price p.p.
05/09/2026 Contact Us	11/09/2026	£2,195.00
15/05/2027	21/05/2027	£2,295.00
12/09/2027	18/09/2027	£2,295.00

Staying in lovely Tuscan accommodation overlooking stunning landscapes
Riding the Montagnola trails, the location of a well-known Sienese MTB race
Sampling the best wines of Chianti, Montepulciano and Montalcino
Riding down the Crete Senesi on a roller-coaster ridge ride
Enjoying the journey across Tuscany on a variety of terrain
Visiting the famous hilltop towns of San Gimignano, Monteriggioni, San Quirico d‘Orcia and Pienza

Self-Guided

Italy

Classic Tuscany

Self-Guided Leisure Cycling Holiday

Duration

8 days

Prices from

£1,495 P.P.

Grade 3 : Moderate

Classic Tuscany

Self-Guided Leisure Cycling Holiday

E-BIKE HIRE AVAILABLE

This tour is well-suited to both regular bikes and pedal assist e-bikes, and you can choose to hire either when you book your tour with us. Confident cyclists will enjoy the boost from a battery for those cheeky climbs, and with less effort required on the bike, you’ll have more energy at the end of the day for off-the-bike activities.

Start Date	End Date	Price p.p.
25/09/2026 Guaranteed	02/10/2026	£1,495.00

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 throughout July and August)

Season 1 – £1695 29 Mar – 14 Jun and 09 Sep – 26 Oct

Season 2 – £1995 15-30 Jun and 01-08 Sep

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

Season 1 – £1775 30 Mar – 14 Jun and 09 Sep – 26 Oct

Season 2 – £2095 15-30 Jun and 01-08 Sep

Alternatively for a great value holiday, please select one of our scheduled departures below.

Staying at Tuscan farms overlooking stunning countryside
Visiting the famous towns of Monteriggioni, Buonconvento, Asciano and Siena
Riding through wonderful landscapes, wide open fields, cypress-lined hills and vineyards
Trying delicious, regional dishes
Sampling the best wines of Chianti, Montepulciano and Montalcino
Absorbing the atmosphere of San Gimignano – a UNESCO World Heritage Site

Self-Guided

Italy

Tuscany - Pisa to Florence

Self-Guided Leisure Cycling Holiday

Duration

8 days

Prices from

£1,295 P.P.

Grade 2-3: Gentle/Moderate

Tuscany - Pisa to Florence

Self-Guided Leisure Cycling Holiday

E-BIKE HIRE AVAILABLE

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 throughout July and August)

Season 1 – £1295 29 Mar – 14 Jun and 09 Sep – 26 Oct

Season 2 – £1495 15 – 30 Jun and 01 – 08 Sep

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

Season 1 – £1355 30 Mar – 14 Jun and 09 Sep – 26 Oct

Season 2 – £1565 15 – 30 Jun and 01 – 08 Sep

Riding between two of Italy’s most iconic cities
Exploring Pisa, home of the world-famous Piazza dei Miracoli
Cycling along quiet country lanes through Tuscan countryside
Cycling past fairy tale Renaissance palaces and villas
Visiting Vinci, the birthplace of Leonardo da Vinci
Spending a free day in Florence, the birthplace of the Renaissance