1-888-414-6437   info@skedaddle.com

A Taste of Tuscany

Guided Bike Tour




7 days

Prices from

$2,130 P.P.
This fantastic cycling holiday in Italy 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. The rolling green countryside will be the backdrop for most of our ride and we'll have the chance to to explore some of the most classic and beautiful areas in the whole of Tuscany: from the wine region of Chianti to the Crete Senesi and the Val D'Orcia. 
As we cycle through Tuscany's natural beauty, we'll experience thrilling riding along steep valleys, dense forests, rivers and the legendary routes from Volterra to San Gimignano, Monteriggioni and on to Radda in Chianti and Siena.
After arriving in Pisa we'll drive through the Tuscan landscape, arriving at our first accommodation in Volterra, one of the many historical towns we'll be visiting throughout the week. The subsequent days will see us following quiet roads, riding past picturesque farmhouses nestled amidst olive groves, vineyards and forests on our way to the medieval towns of Abbadia Isola, Monteriggioni, Radda in Chianti and Siena. Towns steeped in Italian Renaissance atmosphere, scattered with great restaurants, superb gelaterias and the excellent wines of Chianti and Montalcino, what better way to visit Tuscany?
Our Taste of Tuscany holiday is run as a fully guided tour with two set departures per year. However, if you enjoy a little more freedom and flexibility then we do have a slightly gentler, self-guided version of this holiday available. 


  • Visiting the famous towns of Volterra, San Gimignano, Monteriggioni, Radda in Chianti and Siena
  • Riding through wonderful landscapes, wide open fields, cypress-lined hills and vineyards
  • Tasting delicious regional culinary specialities
  • Sampling the best wines of Chianti, Montepulciano and Montalcino
  • Experiencing Italian culture at its finest
  • Having an afternoon aperitivo in Piazza del Campo in Siena

Back to Top


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 (depending on flight times) to walk around and enjoy your first day in Tuscany. In the evening you can enjoy a nice dinner full of local specialties and meet the other members of your group. (Transfer approx. 1.5 hrs).

Day 2
Volterra to San Gimignano
25 Miles / 40 Kms Approx.
  • Meals: Breakfast, dinner
  • Ascent: 550 Metres Approx.

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

We’ll follow the Val D‘Elsa on a rolling road that will take us from rural countryside to a more mountainous area of dense forest. We are now 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 we’ll 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 we’ll take a walk through its narrow streets – a great opportunity for our first Italian gelato! (Our hotel for the night is usually just outside of San Gimignano).

Day 3
San Gimignano to Monteriggioni
25 Miles / 40 Kms Approx.
  • Meals: Breakfast, lunch
  • Ascent: 740 Metres Approx.

Today we’ll start heading south, descending towards the plains of Colle Val d‘Elsa. We’ll ride past woodland and cultivated fields making our way 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.

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

We’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 us straight to our accommodation, 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 Radda in Chianti
21 Miles / 35 Kms Approx.
  • Meals: Breakfast, lunch
  • Ascent: 650 Metres Approx.

Today we face the most difficult stage of the week, with a climb through the Chianti region. Don’t worry though, it will be rewarded with great views and a glass of Chianti wine at the end of the day!

We’ll continue our ride past vineyards and dense oak forests towards Radda in Chianti, our home for the evening. 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 can explore Radda, the perfect place to pick up some local specialties.

Day 5
Radda in Chianti to Asciano
31 Miles / 50 Kms Approx.
  • Meals: Breakfast, lunch, dinner
  • Ascent: 680 Metres Approx.

After breakfast we’ll set off for a stunning ride 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, where we’ll stop for a morning coffee and a chance to look around.

Back on our bikes, we’ll continue our ride on the Lauretana route, once a paved Roman road filled with travellers, artists and pilgrims. We’ll ride through the spectacularly eroded clay badlands landscape, reaching Asciano, a walled city that has its origins in the founding of Rome.

The legend goes that the sons of Remus (Aschio and Senio) fled the newly founded city of Rome that their uncle Romulus ruled. Senio camped on the banks of the river Tresa, while Aschio settled on the left bank of the river Ombrone, founding new settlements, Asciano and Siena respectively.

Day 6
Asciano to Siena
28 Miles / 45 Kms Approx.
  • Meals: Breakfast, lunch
  • Ascent: 920 Metres Approx.

Today is our final day on the bikes with Siena our destination. We’ll ride a section of the “Eroica” route towards Castelnuovo Berardenga. 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, we’ll be on our way again, 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 will lead us straight to the heart of the city: Piazza del Campo where the famous Palio takes place. We deserve a toast with a glass of wine to celebrate the end of the tour in one of the elegant bars overlooking this vibrant square, (and since we’ve spent the week cycling through the Chianti region this may just be our tipple of choice)!

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

Today we say ciao to this beautiful part of Italy and transfer back to Pisa airport for flights home. (Transfer approx. 2 hours)

Back to Top

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 6 riding Colline Senesi, will prove the most challenging following a roller coaster route with some gravel sections.

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


Leisure Cycling Grade

Grade 3 : Moderate

Distances generally between 20-45 miles / 32-72 kms per day

For the leisure cyclist with a good level of physical fitness

May include some steeper, cheeky 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?

Although you may not cycle everyday, you do keep yourself relatively fit and maybe enjoy an afternoon out on your bike at the weekend. Your preference is perhaps for flatter terrain but you don’t mind tackling some hills, and the occasional steep climb if you can take it at your own pace. For those happy to tackle some ups and downs, and possibly some sections of varying terrain (eg. forest tracks, gravel paths etc) we’d recommend our grade 3 trips. We’d generally expect those on a Grade 3 trip to have a decent level of physical fitness and be comfortable with some longer days in the saddle.

Back to Top

Dates & Prices

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.

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) Full tour service, including Skedaddle guides

D) Unless stated, at least one leader qualified in first aid

E) Support vehicle and luggage transfers

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

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

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, on request)

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

Back to Top

The Essentials

Travel Options

Your tour starts in Volterra and finishes in Siena. Group airport transfers are included in the cost of your holiday.

To join the airport transfer on arrival you’ll need to arrive into Pisa Airport (PSA) before 11.00 in time for an 11.30 transfer.

At the end of the tour, we will transfer the group to Pisa Airport, with an estimated arrival time of 10.30 – please consider this when booking your return travel and allow enough time to check in for your chosen flight.

Most flights from North America require overnight travel, and a stop over in an intermediary airport. Flying from North America may involve multiple travel days.

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.


Accommodation will be a mixture of 3 and 4* hotels and agriturismi. Which have been carefully selected for their location, cuisine and service.

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 either Giant Roam, Liv Rove or Focus Univega Geo hybrid bikes (or equivalent).

We also have electric bikes available to rent on request. These bikes are typically Giant Explore E+, Liv Amiti E+ or Focus Univega Geo E e-hybrid 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.

We can provide a helmet locally on request, please let us know if you’d like to rent one when you make your booking.

Rental bikes will be provided with a pannier rack and 1 bag. Your guides will be carrying everything else you’ll need, including all necessary spares.

Back to Top

News, Reviews & Stories

Travel with the seasons in 2022

Hear from our specialists! Your chance to marvel at the authentic experiences that that make these places so special...

UNESCO Italy: Cycle through history…

Tuscan Tastes: Buon appetito!




You May Also Like...

Back to Top