Bike Tuscany | Italy

Explore the beautiful Tuscan countryside on this cycling holiday. Rural Tuscany showcases rolling green hills with medieval tile roofed towns scattered alongside churches and stone farmhouses.  The countryside will be the backdrop for most of your ride where you will ride along steep valleys, dense forests and rivers. There will also be the chance to explore some of the most beautiful areas in Tuscany, including the Crete Senesi and the Val d’Orcia.  After a day of riding visit some of the best restaurants and fantastic gelaterias.


6 nights from $2,732pp* | Flights are additional

Where you’ll visit:

  • Italy

Click on the interactive trip map below to explore the route.


  • Visiting the famous towns of Volterra, San Gimignano, Monteriggioni, Asciano and Siena
  • Riding through beautiful landscapes, wide open fields and vineyards
  • Tasting delicious regional culinary dishses
  • Sample the best wines of Chianti, Montepulciano and Montalcino
  • Immersed in Italian culture
  • An afternoon aperitivo in Piazza del Campo in Siena

What's Included?


  • Return airport transfers
  • 6 nights accommodation | Includes: breakfasts, 5 lunches, 2 dinners
  • 5 days biking
  • Vineyard visit and wine tasting
  • Vehicle support and transfer

Excludes: Airfares, insurance bike and helmet hire

Trip Itinerary

Day 1 – Arrival into Pisa Airport – Transfer to Volterra

After transferring from Pisa airport you will check in at your hotel in Volterra. Located just a short distance away from the old part of town, you should have time  to walk around and enjoy your first day in Tuscany. In the evening you can enjoy a nice dinner full of local specialities and meet the other members of your group.

Day 2 – Volterra to San Gimignano

Leaving the walls of Volterra behind you, we will soon embark on a breathtaking descent. Riding past isolated farmhouses surrounded by green fields, between rows of olive trees and cypresses, you will soon be well acquainted with just how beautiful this part of Italy really is.

Following the Val D‘Elsa on a rolling road that will take you from rural countryside to a more mountainous area of dense forest before arriving in the ‘Oasi Naturale di Castelvecchio” whose special micro climate has allowed the existence of a strong biodiversity and the survival of rare bird species such as the peregrine falcon.

Pedalling on, the view will open up and you will soon get a glimpse of the towers of San Gimignano. This fascinating “town of towers” is one of the prettiest and best-preserved medieval settlements in the whole of Italy. San Gimignano is also known for its white wine, Vernaccia di San Gimignano which is grown in the area. The old town is a UNESCO World Heritage site and you will have the chance to take a walk through its narrow streets – a great opportunity for Italian gelato!

Day 3 – San Gimignano to Monteriggioni 

Today you will be heading south, descending towards the plains of Colle Val d‘Elsa. We’ll ride past woodland and cultivated fields towards the hill-top town of Casole d‘Elsa. The last four kilometres are challenging but the view from the top of the climb will hopefully outweigh the effort.

There should be time to wander through this authentic medieval town, far away from the tourists and clichés of Tuscany.

Leaving Casole d‘Elsa on a rolling road passing small stone villages scattered throughout the countryside. Sections of the route are part of the Via Francigena, the pilgrimage route from Canterbury to Rome.

This ancient road will lead us straight to the next accommodation stop, in an ancient medieval village, surrounded by vast vineyards; an ideal place to taste the local wines. You’ve earned it!

Day 4 – Monteriggioni to Buonconvento

Today will be the longest and most difficult stage of the week, with a roller-coaster route through the western side of Siena. Don’t worry though, each new climb will be rewarded with a fantastic descent!

The first climb takes you to the Castle of Monteriggioni with its 13th century architecture. The massive walls here are linked with Dante’s Divine Comedy and, at that time, served as a defensive stronghold of the town of Siena against rival Florence.

The road continues rolling through the Val di Merse, a natural bridge between the Sienese hinterland and the Tyrrhenian coast. Here discover Le Crete, the ‘badlands’ of Tuscany with classic scenes of rolling landscape lined with cyprus trees.

We will also stop in the Etruscan hamlet of Murlo, yet another small stone fortified village, ideal for a coffee or ice cream break.

Continuing our ride towards Buonconvento, the stop for the evening, a short transfer will take us to the outskirts of Montalcino, where its a chance to visit a family-run organic winery and enjoy a taste of Brunello wine overlooking the rolling hills.

Day 5 – Buonconvento to Asciano

After breakfast its time to set off for a stunning ride through the spectacularly eroded clay badlands landscape. The Lauretana route was once a paved Roman road filled with travellers, artists and pilgrims and leads to the famous 13th century monastery of Monte Oliveto Maggiore with its colourful frescos and botanical garden.

After admiring the artwork we will continue along the winding road over vast open fields before our next stop at San Giovanni D‘Asso before moving on to Asciano, a walled city that has its origins in the founding of Rome.

Day 6 – Asciano to Siena

Today is the final day on the bikes with Siena the next destination. Heading back onto the Lauretana route towards Castelnuovo Berardenga’s. Considered a marginal suburb of Siena, it’s actually a city full of charm, character and history.

After having a look around Castelnuovo Berardenga’s architecture and gardens, its back on the bike, following a mix of tarmac and gravel roads as we get closer to Siena, with glimpses of bell towers and churches. Entering Siena from the Porta Romana leading straight to the heart of the city: Piazza del Campo where the famous Palio takes place. Celebrate the end of the tour in one of the elegant bars overlooking this vibrant square.

 Day 7 – Departure from Siena

Today we say ciao to this beautiful part of Italy and transfer back to Pisa airport for flights home.


Terms and Conditions

  • Price based on per person twin share, in AUD, land only and selected travel periods and blackout dates apply.
  • Prices are correct at the time of release and are subject to availability and to change without notice.
  • Allows for two changes of the following: departure date and/or tour. Applies to bookings made from March 11th to July 31st, 2020. Change requests must be submitted by phone or email minimum 60 days in advance. Please note: a minimum of 90 days’ notice applies.  Any change in value above the original order will be charged, any value below will be forfeited. Offer does not apply to cancellations please ask when booking for details specific to your tour.
  • Credit/debit card surcharges, singles supplement and cancellation/change fees may apply.
  • Events beyond our control such as currency fluctuations may result in price variations.
  • Priced based on travel dates 26 September – 02 October 2020 | 24 April – 01 May 2021 | 25 September – 02 October 2021
  • Prices exclude (unless specified) airfares, insurance (Note: some insurance companies may deem mountain biking an extreme sport), meals, other activities and all items of a personal nature. Additional levies, government charges, and fees may apply that are beyond our control.
  • Accommodation. Subject to availability. Selected travel dates & blackouts & book by dates apply. Specific room types, bedding configuration, features and amenities may vary.
  • Activities: Where specified are subject to availability and weather dependent. Age, weight and height restrictions may apply.
  • Product is supplied by suppliers with their own terms and conditions.
  • travel&co full terms and conditions apply.