Tuscany cycling holiday through Siena & Chianti

Traverse some of Italy's most idyllic landscapes on two wheels, cycling from village to picturesque village via ancient cities, rolling olive groves and renaissance hill towns - pausing to refuel with delicious Tuscan fare.
Cycling through the Tuscan countryside Wine town of Montepulciano Spa village of Bagno Vignoni Murlo Siena Castellini, Chianti Le Crete San Gimignano Monteriggioni Panzano Greve Florence
£2289To£2419including UK flights
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8 Days
Small group
More info
From £1949 - £1989 excluding flights.
Optional single supplement £410.
Minimum age 16.
Make enquiry

Description of Tuscany cycling holiday through Siena & Chianti

The word “Tuscany” evokes dreamy images of rolling hills draped with olive groves, vineyards and cypress-lined roads, each hill topped with ancient stone towns. Our small group, Tuscany cycling holiday makes the most of these classic landscapes – as well as the superb food and wines it produces. There is only one way to truly immerse yourself in the Tuscan way of life – and that is to be unhurried; this is a cycling holiday, but with time factored in for sitting in piazzas with a glass of Chianti, watching the world go by.

Over the week, we’ll explore several of Tuscany’s distinct regions, including the stunning landscapes around the Renaissance hill town of Montepulciano, the hills of Chianti and the scenic region of “Le Crete”, cycling along quiet roads and through steep passes to reach picturesque towns and villages. Continuing onto Siena, you’ll have a free day to explore this compact Gothic city with its renowned Piazza del Campo and cathedral.

We’ll take a scenic detour past the San Gimignano towers, tucked between hills, and stop off in terracotta-producing villages – before continuing on to Florence, a city that needs no introduction. Stroll around the city, exploring the Duomo, the art galleries and the Ponte Vecchio over the River Arno – or simply rest your legs and sip an Aperol spritz or a dark, restorative caffè.


Price information

£2289To£2419including UK flights
Convert currency:
From £1949 - £1989 excluding flights.
Optional single supplement £410.
Minimum age 16.
Make enquiry

Check dates, prices & availability

Travel guides

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Holiday information

Small group tour, ideal for solos & couples:
Small group travel is not large group travel scaled down. It is modeled on independent travel – but with the advantage of a group leader to take care of the itinerary, accommodation and tickets, and dealing with the language. It’s easy to tick off the big sights independently – but finding those one-off experiences, local festivals, travelling markets and secret viewpoints is almost impossible for someone without the insider knowledge gained from years in the field. For those with limited time, a small group tour will save valuable time in planning, and on holiday.


1 Reviews of Tuscany cycling holiday through Siena & Chianti

5 out of 5 stars

Reviewed on 02 Jun 2023 by

1. What was the most memorable or exciting part of your holiday?

Cycling small lanes in Val d’Orcia

2. What tips would you give other travellers booking this holiday?

The information about the trip was accurate and helps with packing the right kit etc.

3. Did you feel that your holiday benefited local people, reduced environmental impacts or supported conservation?


4. Finally, how would you rate your holiday overall?


Responsible Travel

As the pioneers of responsible tourism, we've screened this (and every) holiday so that you can travel knowing it will help support the places and people that you visit, and the planet. Read how below.


Water is a really important issue with cycling trips and whilst we must stay hydrated, it is also vital to provide water without causing lots of waste with plastic bottles. Our guides always provide large bottles used to fill the singular bottles.

Cycling trips in general have a minimal impact on the environment; clients are briefed on managing food waste on cycling days- litter can be collected by guide in support vehicle and disposed of appropriately, in respect of local recycling policies. As this is a cycling trip, clients will interact with locals on scheduled stops, but also on the roads while cycling.

UK office
It all starts at home so we have first worked at reducing our carbon footprint in our UK offices. Through energy conservation measures and recycling policies in place, we are proud to be actively reducing the waste produced and our impact on the environment. We support various projects all over the world to try and give something back to the places we visit.

Group size
We operate small group tours that have a low impact on the communities we visit and we always ensure our operations do not disrupt or lead to the displacement of local people. This allows us to stay in unique and characterful accommodation that may not have otherwise benefitted from tourism due to their limited size.


Local Craft and Culture:
This tour is packed with culture: we visit the cities of Florence and Siena and also a number of small towns along our route like San Quirico, one of the most beautiful and charming medieval towns of the Orcia Valley, the thermal baths of Bagno Vignoni and we cycle the Via Francigena.

This trip is designed to allow a high degree of economic benefit to the local communities; we buy local produce, eat local food including a few gelatos made from artisans parlours, some of which who make unique flavours like blackberry, lavender, gorgonzola cheese and walnuts on top of the favourites, all produced daily with the freshest ingredients. When visiting Castello di Brolio, the guests have the opportunity to taste some of the region’s finest wines including the Barone Ricasoli, recently selected by Wine Spectator as one of the five best wines in the world.
This cycling tour actively encourages guests to chat with local people, visit local cafes and bars, purchase local produce, gifts and crafts and discover the real Tuscan life.

Accommodation and Meals:
On this tour we will spend 7 nights in small hotels. All accommodation is locally owned and staffed, which provides employment and income alternatives for many locals. Where meals are provided, there is a focus on using locally sourced produce and traditional ingredients in locally-run establishments. For meals that are not included, clients are encouraged to eat in authentic, family-run restaurants that showcase the best of Italian cuisine prepared from local produce and to ensure the local communities benefit from our visit. In the village of Vescovado di Murlo we will enjoy a delicious lunch prepared by Gianluca, the owner of the small, family owned Albergo di Murlo. The wild Boar Pappardelle or Pici is a must try dish here.

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