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Classic Tuscany

Self-Guided Leisure Bike Tour




7 days

Prices from

$1,585 P.P.

Classic Tuscany

Self-Guided Leisure Bike Tour




7 days

Prices from

$1,585 P.P.
A fantastic cycling holiday in Italy that really showcases the beautiful Tuscan countryside. Rural Tuscany is synonymous with undulating green hills capped by medieval, tile-roofed towns, punctuated by cypresses, churches and stone farmhouses, delicious wine and authentic Italian food.
Rolling green countryside will be the backdrop for most of your Tuscany cyling holiday and you'll have the chance to explore the Chianti region and the Crete Senesi which are among the most classic and beautiful areas in the whole of Tuscany.
As you journey on this cycling holiday in Tuscany you'll take in its natural beauty, and experience varied riding taking you through dense forests and alongside rivers and the legendary routes from San Gimignano, to Monteriggioni and on to Siena.
After arriving in Pisa we'll transfer you through Tuscan landscape, arriving at your first accommodation in San Gimignano, one of the many historical towns you'll be visiting throughout the week.
The subsequent days will see you following quiet roads, riding past picturesque farmhouses nestled amidst olive groves, vineyards and forests on your way to the medieval towns of Abbadia Isola, Monteriggioni, Radda in Chianti and Siena. With towns oozing the Italian Renaissance atmosphere, scattered with great restaurants, superb gelaterias and the excellent wines of Chianti and Montalcino, there's no better way to explore Tuscany than by bike! 


  • Staying at Tuscan farms overlooking stunning countryside
  • Visiting the famous towns of Monteriggioni, Radda in Chianti 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

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Day 1
Arrival into Pisa Airport - Transfer to San Gimignano

Arrival into Pisa airport and transfer to San Gimignano (transfer approx. 1.5 hours). Depending on your arrival time and local arrangements we may arrange for your local representative to meet you either tonight or tomorrow morning to fit you to your rental bikes (if renting) and conduct your welcome meeting. Details will be confirmed for you ahead of your departure. After checking into your accommodation you will have the rest of the day to explore the local area and get prepared for your first day of cycling.

Day 2
San Gimignano to Casole d'Elsa
18 Miles / 32 Kms Approx
  • Meals: Breakfast
  • Ascent: 500 Metres Approx.

The fascinating town of San Gimignano is the town of towers and 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. We recommend taking a walk through its narrow streets – a great opportunity to absorb the Tuscan atmosphere. Back on the bikes you will descend towards the plains of Colle Val d‘Elsa. You’ll ride past woodland and cultivated fields making your way towards the hill-top town of Casole d‘Elsa. The last few kilometres are challenging but the views from the top of the hill will certainly outweigh the effort. You’ll have some time to wander through this authentic medieval town, far away from the tourists and clichés of Tuscany. The accommodation is set just outside the walled centre, a short walk into town and where you can enjoy an evening drink. We recommend watching the sunset from the bastions overlooking the hills of Tuscany.

Day 3
Casole d'Elsa to Strove (near Monteriggioni)
20 Miles / 35 Kms Approx
  • Meals: Breakfast
  • Ascent: 400 Metres Approx.

You’ll leave 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 you straight to your accommodation, in an ancient medieval village, surrounded by vast vineyards; an ideal place to taste the local wines. A short cycle away from your accommodation you’ll find Abbadia Isola.

The fields surrounding Abbadia Isola were once a large swamp or bog that accumulated rain water from Monte Maggio. ‘Isola’ refers to an island or the only solid piece of land on which the original ancient hamlet was built. The Abbey of St Salvatore was founded in the 11th century and was an important strategic crossroad on the Via Francigena between Florence, Fiesole, Siena and Volterra. Now the Abbey is surrounded by flat fields filled with sunflowers in summer, and it’s an easy-going and enjoyable cycle from your accommodation.

Day 4
Strove to Radda in Chianti
19 Miles / 32 Kms Approx
  • Meals: Breakfast
  • Ascent: 600 Metres Approx.

Today is the toughest stage of the week, with a roller coaster ride through the northwestern side of Siena and into the Chianti region. 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. A gentle stroll through the narrow streets is a must, as well as a cycle round the fortified walls. Back on the bikes, you’ll head towards Castellina in Chianti. You will soon realise you are cycling in wine territory as you pass acre after acre of vineyards. Castellina in Chianti is well worth exploring on foot; its importance is not only connected to wine, but also to the abundance of Etruscan sites found in this region.

Such rich archeological heritage justifies a visit to the territorial museum for Chianti Senese, its collection including findings not only from the township of Castellina in Chianti, but from Castelnuovo Berardenga, Gaiole in Chianti and Radda in Chianti as well. Leaving Castellina, another 11 Kms will take you to Radda in Chianti, a beautiful medieval town enclosed in large defensive walls.

Day 5
Chianti Loop Ride
19 Miles / 30 Kms Approx.
  • Meals: Breakfast
  • Ascent: 500 Metres Approx.

Today’s route will be a gentle roller coaster through the Chianti region of oak forests and vineyards. The day will start with a gentle descent past vineyards towards Gaiole in Chianti, where you can take a slight detour to visit the town. The birthplace of Chianti Classico, Gaiole is celebrated in its own right.

In medieval times it was one of the three capitals of the Chianti League, along with Castellina and Radda. The hilltop town is set among oak and chestnut forests but also surveys vineyards and olive groves. As a former military stronghold, Gaiole is ringed by medieval castles and fortified abbeys. Today Gaiole is also known as the birthplace of the “Eroica” (1997) a vintage cycling event, that brings thousands of riders in the region cycling along the “strade bianche“. Gaiole is a perfect stop for a long lunch, before cycling back to Radda in Chianti.

Day 6
Radda in Chianti to Siena
25 Miles / 40 Kms Approx.
  • Meals: Breakfast
  • Ascent: 550 Metres Approx.

Today’s route will be a gentle roller coaster through the Chianti region of oak forests and vineyards. The day will start with a gentle descent, the landscape changing from oak forests to cultivated fields as you make your way towards Siena.

This whole region is dotted with castles, once defensive systems but now privately owned by wine producers. Your route will then take you past Meleto, San Donato in Perano and Brolio Castle. You’ll follow a mixture of tarmac and “strade bianche” (gravel roads) as you get closer to Siena, with glimpses of bell towers and churches.

Entering Siena from the Porta Romana will lead you straight to the heart of the city, Piazza del Campo, where the famous Palio takes place. There will be time to wander through Siena in the late afternoon, with a visit to the Palio Square and the Duomo, before heading out to dinner for a mouthwatering Tuscan meal.

Day 7
Departure from Siena - Transfer to Pisa Airport
  • Meals: Breakfast

Today you’ll say ciao to this beautiful part of Italy and we’ll transfer you back to Pisa airport for your outgoing flight. (Transfer approx. 1.5 hours.)

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The Cycling


Tuscany is a region with rolling hills of cultivated fields, woodland and chalky landscape, dotted with hill-top hamlets. Riding is mostly on quiet tarmac roads (95% – shared with traffic, can be busier in the summer months) and some well-beaten gravel roads (5% – mostly strade bianche), with days involving riding up to hill-top towns.

You will find certain sections have some steeper more challenging climbs. Day 4 riding up to the Chianti region will prove the most challenging following a roller coaster route.

We recommend hybrid bikes for this tour, but it’s possible to cycle the route on a gravel, or road bike, bearing in mind there are some short gravel sections


Leisure Cycling Grade

Grade 2-3: Gentle/ Moderate

Aspects of both our grade 2 and 3 trips

Suitable for those looking for some cycle friendly routes

Some modest climbs

Possibly sections of varying terrain (eg. forest tracks, gravel paths etc)

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?

Trips that are graded as a 2-3, will have aspects of both our grade 2 and 3 rides. These tours are still suitable for those perhaps who have recently got into cycling, and offer an array of accessible, cycle friendly routes, cycle paths and quiet roads, however there will be some days / sections where you may have to tackle some ups and downs, the occasional steeper climb and perhaps some varying terrain (forest tracks, gravel paths etc). Suitable for those with a decent level of physical fitness, looking for some leisurely rides with occasional (achievable!) challenges along the way.  

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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.

2023 25 Mar – 30 Oct

Season 1 – $1585 25 Mar – 05 Apr, 15 Apr – 17 Jun and 04 Sep – 30 Oct

Season 2 – $1970 06 Apr – 14 Apr and 18 Jun – 03 Sep

2024 25 Mar – 30 Oct

Season 1 – $1695 03 Apr – 17 Jun – 04 Sep – 30 Oct

Season 2 – $2115 25 Mar – 02 Apr – 18 Jun – 03 Sep

Alternatively for a great value holiday choose one of our scheduled departures below.

Secure Your Holiday With A Deposit

Book your trip with a deposit of $250 per person until 60 days before departure.

Choose your dates to start the booking
Start Date
End Date
Price p.p.
Start Date
Return Date
7 days

Whats Included Tick

A) Accommodation (shared twin / double en suite rooms) in small hotels / agriturismi / guesthouses

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

C) English-speaking local representative (with welcome meeting)

D) Access to the Skedaddle 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) Single room (available if required)

D) Travel insurance

E) Meals not stated in the itinerary

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) Local tourist tax (to be paid locally – Approx. 2€ per day)

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

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The Essentials

Travel Options

Your tour starts in San Gimignano and finishes in Siena.

Airport transfers are included in the cost of your holiday. 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 12.00 and 19.00.

If you are joining one of our scheduled departures we will provide arrival and departure times, along with suitable flight options, as and when more flight schedules are released.

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 your accommodation (shared twin or double en suite rooms) will be in a mixture of 3 and 4* hotels, guesthouses and agriturismi.

We have an accommodation upgrade option available on this tour, if you’d prefer to stay in 4* hotels; this will include an upgrade on 4 nights of 6. Please select this supplement at the time of booking.

Bike Hire

If you don’t own a suitable bike or would prefer to avoid bringing your own we have bikes available to rent. These bikes are typically Focus Univega Geo hybrid bikes (or equivalent).

We also have electric bikes available to rent on request; these will typically be Focus Univega GEO E-bikes (or equivalent). It may take us a day or so to confirm availability so please let us know as soon as possible if you’d like to take this option.

Rental bikes will be provided with a pannier rack and 1 bag, a puncture repair kit, spare inner tubes (2), a bike lock, a bike pump, a water bottle holder and a phone mount.

We can provide a helmet locally on request, please let us know if you’d like to rent one when you make your booking. It is possible to bring your own saddle and / or pedals, but please let us know in advance.

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