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Tuscany - Giro della Toscana

Self-Guided Road Cycling Holiday




8 days

Prices from

£1,595 P.P.
A mid-level road cycling tour exploring one of the country's premier destinations. Tuscany - the word itself is evocative, conjuring images of classic landscapes, rolling hills, cypress trees and medieval hilltop towns.
The region also offers superb cycling attracting riders from all over the world. You will spend your first evening in the charming medieval town of Casciana Terme, a spa town retreat scattered with great restaurants and superb gelateria.
The following morning you will head south through 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 on you'll 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 you’ll be spending evenings in both Montalcino and Chianti where you can enjoy a glass or two of Brunello and Classico.
Finally you'll head for the atmospheric twin castled hilltop town of Volterra. On your final day on the bikes you return to Casciana Terme in good time to take advantage of the town's soothing thermal waters and wind down before your flight home.

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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A fantastic holiday discovering beautiful hilltop villages, meeting some great local people and enjoying wonderful food and wine. Can’t thank the team enough!

Jerry, Hampshire


Day 1
Arrival: Pisa / Casciane Terme
Non Riding Day

Following arrival at Pisa airport (PSA), we will transfer you to the charming town of Casciana Terme, a spa town retreat. You will receive your road book and we will provide you with all the information you will need for the duration of your trip, before we leave you to start your self-guided tour of Tuscany. Depending on your arrival time, 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
35 Miles / 57 Kms Approx.
  • Meals: Breakfast
  • Ascent: 1,050 Metres Approx.

Your first day’s ride will take you from Casciana Terme to the gem of Tuscany, San Gimignano. Leaving the hills around Pisa, the riding is gentle as you roller coaster along the roads of the ‘Colli Pisane‘, taking a network of minor roads past woodland, vineyards and small towns.

Just before you stop for your lunch you gradually climb through lush green woods, before the final descent towards San Gimignano. You will stop in your tracks as the view opens up, ahead of you the ‘Town of Towers’ and one of the prettiest and best preserved medieval settlements in Italy.

You should have plenty of time to walk around San Gimignano, climb one of the towers and taste the ice cream which won 1st prize at the world ice cream championships. A short ride will take you to your 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 your first day riding in Tuscany!

Day 3
San Gimignano to Radda in Chianti
32 Miles / 52 Kms Approx.
  • Meals: Breakfast
  • Ascent: 1,000 Metres Approx.

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

You will have time to ride up and through many of these small towns, absorbing the whole Tuscan experience. With incredible views, intimate piazzas and some wonderful boutiques and art galleries, these towns make a perfect itinerary for your bike ride. Your destination for today is Radda in Chianti.

Staying at the accommodation in the centre of Radda in Chianti, you have time to enjoy the atmosphere of this hill top town and indulge in some fine wine tasting and dining at some of the best restaurants of the region.

Day 4
Radda in Chianti to Pienza
51 Miles / 82 Kms Approx.
  • Meals: Breakfast
  • Ascent: 1,400 Metres Approx.

Today you leave Radda in Chianti and ride through Gaiole and on to Castelnuovo Berardenga, on your way to Pienza. Today’s ride takes you 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.

You will then ride past Meleto, San Donato in Perano and Brolio Castle. You can rest your legs in Asciano, yet another little medieval town set on a hillside, above the Ombrone Valley.

After a final roller coaster climb through the ‘Colli Sienesi‘, you will reach Pienza, your destination for today’s ride, the quintessential renaissance town in Tuscany.

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

Pienza is 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, you 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 the Italian landscape. You then 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. On to Castiglione d’Orcia with its picturesque stone paved streets and Romanesque church, the final climb of the day will take you to the quintessentially Tuscan hill town of Montalcino.

Narrow streets lined with boutiques, art shops and wine shops allows for a relaxing time. For wine lovers, Montalcino Brunello wines can be tasted in one of the many wine bars, savouring some of the best reds that the area has to offer.

Day 6
Montalcino to Casole d'Elsa
51 Miles / 82 Kms Approx.
  • Meals: Breakfast
  • Ascent: 1,300 Metres Approx.

You are getting to the end of your cycling in 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 you back down into Val d‘Orcia. Today’s riding will be a gentle roller coaster of superb riding through more countryside and farmland. Your destination for today is Casole d‘Elsa, a cobbled medieval town set on top of a hill, barely visited by tourists. Rewarded by the views and yet another gelato stop, you move in to your accommodation. After a dip in the pool you can then head back up to Casole for dinner at a traditional ‘osteria‘.

Day 7
Casole d’Elsa to Casciana Terme
45 Miles / 70 Kms Approx.
  • Meals: Breakfast
  • Ascent: 1,050 Metres Approx.

Your final day’s ride will take you back towards the rolling Pisan hills and Casciana Terme. Taking a network of minor roads, eventually ascending to Volterra, one of Tuscany’s most evocative hill towns. From the Etruscan gates to the remains of the Roman forum, you’ll capture the real Italian experience here. Arriving early afternoon in Casciana Terme, not only will it give you time to sort out your bikes but also to make the most of the hot springs 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

It’s time for us to meet up with you again and transfer you back to Pisa airport for your flight home. (Transfer time approx 45 minutes).

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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 offer alternative routes to riders who prefer not to ride these short un-surfaced stages.

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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 loved the variety of scenery, awesome views and beautiful towns! The representatives were very helpful and ensured we had all we needed for our self-guided trip.

Angela, Hampshire

Dates & Prices

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

2024 25 Mar – 30 Oct

Season 1 – £1595 03 Apr – 17 Jun / 04 Sep – 30 Oct

Season 2 – £1825 25 Mar – 02 Apr / 18 Jun – 03 Sep

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
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) Local representative (with either in person or video welcome meeting)

D) Access to the navigation app for holiday information and navigation

E) Luggage transfers

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

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

H) 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) City tax to be paid at each accommodation (amount varies)

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

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The Essentials

Travel Options

This tour starts and finishes in Casciane Terme.

Airport transfers are included in the cost of your tour. We ask that you fly into and back from Pisa airport (PSA). Please aim to arrive between 09:00 and 16:00 and depart between 11:00 and 19:00.

Please check with Skedaddle before making any travel arrangements.

Please note – If you make travel arrangements that fall outside of the above time windows there may be an additional charge for your transfers.


The majority of our accommodation (shared twin or double rooms) will usually be en-suite in 3* hotels or agriturismi.

If you would like us to check out accommodation upgrade options for you, please contact us for details.

Please note that some of the accommodation we use have long gravel entrances.

Bike Hire

If you have opted to rent, your bike will typically be a Giant Defy 1. They are great bikes with good quality components, mechanical disc brakes and generally come equipped with at least one bottle cage, a saddle bag and a small pump.

If you’d like to upgrade to a full carbon (typically a Wilier) bike, please let us know and we can look into this on request.

We can 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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