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Italy

A Taste of Tuscany

Guided Bike Tour

Grade

1
2
3
4
5

Duration

7 days

Prices from

$1,780 P.P.
Italy

A Taste of Tuscany

Guided Bike Tour

Grade

1
2
3
4
5

Duration

7 days

Prices from

$1,780 P.P.
BOOK NOW
This fantastic cycling vacation 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 explore the Crete Senesi and the Val d'Orcia which are among the most classic and beautiful areas in the whole of Tuscany.
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 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, Buonconvento 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 tour 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 tour available. 
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Highlights

  • Visiting the famous towns of Volterra, San Gimignano, Monteriggioni, Asciano 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 Campo in Siena

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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 (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, lunch

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

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 Buonconvento
37 Miles / 60 Kms Approx.
  • Meals: Breakfast, lunch, dinner

Today we face 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 of our climbs takes us 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 we’ll discover Le Crete, the ‘badlands’ of Tuscany with classic scenes of rolling landscape lined with cyprus trees.

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

We’ll continue our ride towards Buonconvento, our home for the evening. One we have freshened up, a short transfer will take us to the outskirts of Montalcino, where we will visit a family-run organic winery and enjoy a taste of Brunello wine overlooking the rolling hills.

Day 5
Buonconvento to Asciano
25 Miles / 40 Kms Approx.
  • Meals: Breakfast, lunch, dinner

After breakfast we’ll 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 it will lead us to the famous 13th century monastery of Monte Oliveto Maggiore with its colourful frescos and botanical garden.

After admiring the artwork, we’ll continue along the winding road over vast open fields before our next stop at San Giovanni D‘Asso. Moving on we’ll reach 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
31 Miles / 50 Kms Approx.
  • Meals: Breakfast, lunch

Today is our final day on the bikes with Siena our destination. We’ll head 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, 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 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)

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The Cycling

Terrain

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. 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.

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Leisure Cycling Grade

1
2
3
4
5
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.

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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
Duration
Price p.p.
Start Date
24/04/2021
Return Date
01/05/2021
Duration
8 days
Price
$1,780.00
Start Date
25/09/2021
Return Date
02/10/2021
Duration
8 days
Price
$1,780.00

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) Vineyard visit and wine tasting (day 4)

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

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

What's not Included Cross

A) Bike hire (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

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The Essentials

Travel Options

You’ll need to arrive into and return from Pisa airport (PSA), according to the following schedules: April Arrive into Pisa airport before 13.30, for a 14.00 transfer. You will arrive back at the airport for flights home at 11.00. September Arrive into Pisa airport before 12.30, for a 13.00 transfer. You will arrive back at the airport for flights home at 11.00.

Most flights from North America require overnight travel, and a stop over in an intermediary airport, with Norwegian combining with another airline being a common combination for this trip. Please note that flying from North America may involve multiple travel days. Please contact us for more detailed information on the specific flight schedules available for your cycling holiday. Please check with us before booking any flights, to make sure we have reached the minimum number required to guarantee your trip and to ensure your flights fit with our scheduled transfers. Please note – If you make travel arrangements that fall outside of the above time windows there may be an additional charge for individual transfers.

Accommodation

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 hire. These bikes are typically Scott Sportster hybrid bikes (or equivalent).

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

Hire 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.

We have electric bikes available to hire on request. 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.

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News, Reviews & Stories

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