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Tuscany - Giro della Toscana

Guided Road Cycling Holiday




8 days

Prices from

£1,895 P.P.
A mid-level road cycling holiday in Italy exploring one of the country's premier cycling destinations - Tuscany. The word itself is evocative, conjuring images of classic Italian landscapes, rolling hills, cypress trees and medieval hilltop towns.
The region also offers superb cycling and is an international training ground, attracting riders from all over the world. We spend our first evening in the charming medieval town of Casciana Terme, a spa town retreat scattered with great restaurants.
The following morning we head south through the olive groves to the atmospheric hilltop town of San Gimignano, a fascinating 'town of towers' and one of the best preserved medieval settlements in Italy.
Moving onwards we ride into the Parco della Val d’Orcia, a World Heritage site with a distinctive landscape of conical hills rising from the flat chalk plains. Wine lovers will be in their element as the tour progresses and we’ll be spending evenings in both the Chianti region and Montalcino where we will set time aside for a glass or two of Classico and Brunello.
Travelling north again through the land which lays between Siena and Florence we head for the atmospheric hilltop town of Volterra. On our final day on the bikes we return to Casciana Terme in good time to take advantage of the town's soothing thermal waters. 

Holiday Highlights

  • 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

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We got to experience what life is like off the beaten track and soak in the fantastic place that Tuscany is. There are not enough superlatives to describe how beautiful the accommodation was!

Robert, Reading


Day 1
Arrival: Pisa / Casciane Terme
Non Riding Day

Following arrival at Italy’s Pisa airport (PSA), we make the short transfer to the charming spa town of Casciana Terme, a quiet retreat where you can spend the rest of the day relaxing and enjoying the facilities.

Depending on flight arrivals, there should also be time to have a quick leg stretch on your bikes before your evening meal in one of the town’s great restaurants.

Day 2
Casciana Terme to San Gimignano
40 Miles / 65 Kms Approx.
  • Meals: Breakfast
  • Ascent: 1,050 Metres Approx.

Our first day’s ride will take us from Casciana Terme to the gem of Tuscany, San Gimignano. Leaving the hills around Pisa, the riding is gentle as we roller-coaster along the roads of the ‘Colli Pisane‘, taking a network of minor roads past woodland, vineyards and small towns. Just before we stop for lunch we gradually climb through lush green woods, before reaching the small walled medieval hill-top town of San Gimignano.

This fascinating ‘town of towers’ is one of the prettiest and best preserved medieval settlements in Italy and we should have some time to walk around the square and taste the World Ice-Cream Championships 1st prize winning ice cream! The town is also known for its white wine Vernaccia di San Gimignano but we might save that for later!

A short ride later will take us to our delightful hotel, surrounded by vineyards and rolling hills. Depending on the time of year, a dip in the pool and relaxing with a drink, makes a great finish on our first day riding in Tuscany!

Day 3
San Gimignano to Radda in Chianti
40 Miles / 65 Kms Approx.
  • Meals: Breakfast, lunch
  • Ascent: 1,500 Metres Approx.

Leaving the charming town of San Gimignano, today’s ride is a roller-coaster through a picturesque landscape of little medieval fortified villages perched on top of hillsides, such as Castellina in Chianti and Radda in Chianti.

We have time to ride up and through many of these small towns, absorbing the whole Tuscan experience along the way. With incredible views, intimate piazzas and some wonderful boutiques and art galleries, these towns make a perfect passage for our journey. Our destination for today is Radda in Chianti.

The village, famous for its wine, is located between the valleys of the rivers Pesa and Arbia on a forested hillside in the Chianti Classico region. After settling into our accommodation, we set off to a renowned ‘Enoteca’ where we have the opportunity to try some of the best of the Chianti wines produced in the region.

Day 4
Radda in Chianti to Pienza
55 Miles / 90 Kms Approx.
  • Meals: Breakfast, lunch
  • Ascent: 1,700 Metres Approx.

Today we leave Radda and ride to Gaiole in Chianti and on to Castelnuovo Berardenga, on our way to Pienza. Today’s ride takes us further south past hills blanketed with vineyards and thick forests. This whole region is dotted with castles, once defensive systems but now privately owned by wine producers.

We ride past Meleto, San Donato in Perano and Brolio Castle. We will rest our legs in Asciano, yet another little medieval town set on a hillside, above the Ombrone Valley. After a final rollercoaster climb through the ‘Colli Sienesi‘, we reach the outskirts of Pienza, our destination for today’s ride, the quintessential renaissance town of Tuscany.

Day 5
Pienza to Montalcino
28 Miles / 45 Kms Approx.
  • Meals: Breakfast
  • Ascent: 900 Metres Approx.

Being a short day, there is time to explore Pienza, a rare example of Renaissance town design. Often described as a ‘utopian city‘, it represents one of the best planned Renaissance towns, where a model of ideal living and government was attempted, based on the concept of a town able to satisfy the needs of a peaceful and hardworking populace. Pienza’s location in the centre of the Val d‘Orcia, a wonderful and untouched valley, helps the town to embody the fundamental principal that humanistic architecture attempted to incorporate – the balanced relationship between Man and Nature.

Leaving Pienza, we continue with a fantastic descent and a superb ride into the heart of Val d’Orcia, a UNESCO heritage region with conical hills lined by cypress trees, the ultimate aesthetic of Italian landscape. We ride on to San Quirico d’Orcia and Bagno Vignoni where legend has it that St Catherine and Pope Pius II both bathed in the thermal waters here. On to Castiglione d’Orcia with its picturesque stone paved streets and Romanesque church, the final climb of the day will take us to the quintessentially Tuscan hilltop town of Montalcino.

Day 6
Montalcino to Strove
52 Miles / 84 Kms Approx.
  • Meals: Breakfast, lunch
  • Ascent: 1,300 Metres Approx.

We are getting to the end of our tour of Tuscany and the riding is smooth along the rolling hills of the region around Montalcino. Leaving the hill town, a long and gradual descent will take us back down into Val d‘Orcia. Today’s riding will be a gentle rollercoaster of superb riding through more countryside and farmland. Our final destination for today is Strove – a very small hamlet not far from the medieval town of Monteriggioni.

Day 7
Strove to Casciana Terme
52 Miles / 83 Kms Approx.
  • Meals: Breakfast, lunch
  • Ascent: 1,350 Metres Approx.

Our final day’s ride will take us back towards Pisa and Casciana Terme. Taking a network of minor roads, we meander over rolling hills, stopping off in Casole d‘Elsa and eventually ascending into Volterra, one of Tuscany’s most evocative hill towns. From the Etruscan gates to the remains of the Roman forum, we’ll capture the real Italian experience here. Arriving early afternoon in Casciana Terme, will not only give us time to pack up our bikes but also to make the most of the hot springs, indulging in thermal baths and more fine dining and wine. A great way to end Italy’s ultimate riding experience.

Day 8
Departure: Casciane Terme / Pisa
Non Riding Day
  • Meals: Breakfast

Time to say our farewells as after breakfast we will take you back to Pisa airport (PSA) for your onward flights.

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The Cycling


We will be riding mostly on well-surfaced tarmac roads, through countryside linking up some of the most important hilltop centres in this stunning region. Tuscany is predominantly hilly, so you can expect climbs every day, some short steep sections, some longer ones, followed by meandering descents.

Tuscany is also famous for its ‘Strade Bianche’ (unsealed white roads) which host their own annual road cycling race; L‘Eroica. You will have an opportunity to ride some short stages of the L‘Eroica route so we recommend that riders avoid super lightweight racing tyres and opt for a slightly more robust tyre, such as a puncture resistant 25c. These will also be useful when on the approach to some of our rural accommodations which are often dirt road or gravel driveways.

Strade Bianche roads are entirely rideable on road bikes however we can provide vehicle transfers or offer alternative routes to riders who prefer not to ride these short unsurfaced stages.

0356 Day 6 Casole D'Elsa.jpg

Road Cycling Grade

Grade 3 : Moderate

45-60 miles / 70-95 kms per day

For riders with experience, good fitness & a decent level of skill

Some features that may be experienced more frequently in a higher grade tour

Most days include a couple of significant climbs

Some long days & some steep to very steep sections

Not for beginners

Our grading guidelines have been carefully created based on our many years of cycling experience, as well as customer feedback from our trips. Of course, if you're still struggling to figure out where you fit on the scale, do feel free to give us a quick call and we'll be more than happy to help!

For more information about our grading system click here.

Is this suitable for you?

You’re definitely not a novice rider, you’re fit, you ride regularly at weekends, sometimes staying on the bike for much of the day, you love your bike! You also enjoy a challenge and if you haven’t already done so you’re keen to attempt a semi-serious to serious mountain pass or two. You’re as comfortable with the prospect of descending from the top of a col as you are with the idea of climbing it and you’re confident that you have the skills to do so safely. You’re not necessarily a “racer” but you can crank up the pace a little when it’s necessary and you don’t mind forgoing a coffee stop if the schedule demands it occasionally. You probably own and use clipless pedals. You have good control of your bike and can take a drink from a water bottle without having to unclip and put your feet on the ground. Whilst you find a full day in the saddle fulfilling you’re not obsessed and as much as you are looking forward to the riding on your holiday, you’re also looking forward to a little local culture and cuisine. Grade 3 would be a good option for you.

For more information about the grading of this holiday in particular, please check out the terrain section which will give you some specifics of what to expect on this tour.

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I really appreciated the efforts and the personal touch put into the spread provided for us. Dinner – absolutely fantastic, I’ll be reminiscing and dreaming about each meal for years to come.

Anita, London

Dates & Prices

Secure Your Holiday With A Deposit

Book now with a £200 deposit and nothing more to pay until 60 days before departure. Choose a date to start your booking and see all prices, including bike hire and single room supplements.

Select a date to view prices and book
Start Date
End Date
Price p.p.
Start Date
Fully Booked
Return Date
8 days
Start Date
Fully Booked
Return Date
8 days

Whats Included Tick

A) Accommodation (shared twin / double en-suite rooms)

B) Meals as per the itinerary (B-Breakfast, L=Lunch, D=Dinner)

C) Full tour service, including Skedaddle guides

D) Unless stated, at least one leader qualified in First Aid

E) GPX files available on request

F) Support vehicle and luggage transfers

G) Airport transfer on scheduled arrival day from Pisa airport (PSA)

H) Airport transfer on scheduled departure day to Pisa airport (PSA)

I) Financial Protection through ABTOT

What's not Included Cross

A) Bike rental (available if required)

B) Flights and charges for travelling with your bike (if applicable)

C) Meals not stated in the itinerary

D) Travel insurance

E) Single room (available if required)

F) Personal clothing and equipment

G) Personal expenditure (souvenirs, bar bills, hotel facilities etc)

H) Entrance fees to museums and other attractions en-route

I) Airport transfers on days other than the scheduled arrival / departure days

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Private Departures

Private Departures

Are you keen to only travel with your family or friends? Struggling to find the right date? Well, we can organise a private departure for this tour and tailor aspects to suit your group's specific needs. Contact our friendly team and we'll help you turn your dream into reality.

The Essentials

Travel Options

Your tour starts and finishes in Casciane Terme. Group airport transfers are included in the cost of your tour. We ask that you arrive and depart into / from Pisa airport (PSA).

Pisa is well served from the UK with various options to consider – easyJet from London Gatwick (LGW), BA from London Heathrow (LHR), Ryanair from London Stansted (STN) and Jet2 / easyJet from Manchester (MAN). Other airlines, non-direct, and regional options may be available, please chat to our team.

We’ll be in touch with suitable flight options as departures confirm and flights become available.

Please check with us before making any travel arrangements to ensure we have reached the minimum number required to guarantee your holiday and to make sure your arrangements fit with our scheduled transfers.

Please note If you make travel arrangements that fall outside of the scheduled transfer windows, there may be an additional charge for individual transfers.


The majority of our accommodation will be en-suite in 3 star guest houses or hotels. Occasionally accommodation will include a swimming pool.

Some of the accommodations we use have long gravel entrances.

Bike Hire

Rental bikes will typically be a Giant Defy Advanced 2 or Giant Liv Avail Advanced 2 (for those preferring a women’s specific geometry) – or equivalent, with a carbon frame and hydraulic disc brakes.

These are great bikes with good quality components generally equipped with at least one bottle cage, a saddle bag and a small pump.

We can also include a helmet which should be requested at time of booking.

Please note that your bike will come with flat pedals as standard, so please do bring your own if you use clip-in pedals.

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