• Departing from? Departing from
  • Travelling to? Travelling to
  • When? When
  • How long for? How long for
  • Clear Search
  • Departing from?Dublin + 3
  • Travelling to?Italy + 1
  • When?March 2015
  • How long for?7 nights
  • Clear Search
Tuscany Cycling Holiday
from Per person

Tuscany Cycling Holiday

  • 7 Night Holiday
  • B&B
View Dates & Prices

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 your ride and you will 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 you cycle through Tuscany's natural beauty, you will experience thrilling rides along steep valleys, dense forests, rivers and the legendary routes from Volterra to San Gimignano, Monteriggioni and on to Siena.

 

After arriving in Pisa you will drive through the Tuscan landscape, towards Volterra, one of the many historical towns you will be visiting throughout this holiday. The subsequent days will see you cycling quiet roads, riding past picturesque farmhouses nestled amidst olive groves, vineyards and forests on your way to the medieval towns of Abbadia Isola, Monteriggioni, Buonconvento and Siena. Soak up the Italian Renaissance atmosphere as you explore traditional Tuscany by bike.

This holiday is ideal for a leisure cyclist with a good level of physical fitness. The cycling distances are between 40 km – 60 km per day on varying terrain, with some steep climbs occasionally included.

 

Practical Information for this holiday

Group Size

In order to offer you as much choice as possible, we work with an expert partner for all cycling holidays. This is not an exclusive TD active Holidays tour. Your group will be made up of a range of travellers from different countries, who share in your passion for cycling. The group sizes are typically between 6 – 16 people.

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. Riding Colline Senesi, will prove the most challenging following a roller coaster route. 

Cycling Guides
TD active Holidays work with a local cycling partner in Italy, who have been running Cycling Holidays for over 20 years now. The expert team of guides are always on hand to make your holiday an unforgettable experience. Our guides in Italy come from all over the country and are immensely proud of their home. They enjoy helping others discover not just the best riding the country has to offer, but also the fantastic range of scenery, traditional food, and Italy’s unique culture and history. The local touch really helps to enhance your experience and helps you get the most from your time in Italy.  Your holiday will be led by 1 or 2 English speaking guides, depending on the size of the group. What places our guides head and shoulders above other cycle leaders is their focus on providing a great cycling experience and excellent customer service; from the very start to the very end of your holiday, you’ll be in safe hands. Our guides take care of all the daily planning and organisation, leaving you free to get on your bike and enjoy the ride
Accommodation
Accommodation will be a mixture of 3 and 4* hotels and agriturismi (local farmhouses)
Food

Italian breakfasts consist of bread and jams, sweet pastries and fruit, supplemented with cooked meats and cheese, yoghurt and cereals. On guided trips our guides pride themselves on their lunches and serve up a great buffet of fresh local treats often supplemented with a pasta dish to keep the legs turning. Evening meals are either taken at a local restaurant or your accommodation. Generally speaking these consist of antipasti (a selection of appetisers), a pasta course, a main course of meat or seasonal vegetables finished off with a sweet dish, fruit, coffee and liqueurs all washed down with the great local wine. Vegetarians and people with specific dietary requirements can be catered for – please indicate at the time of booking if you have any dietary requirements.

Preparation & training

In order to get the most out of your trip, you need to choose a holiday of the right grade and make sure you‘re prepared. The amount of preparation and training you need to do will depend on your own experience, your level of fitness and the type and grade of holiday you are going on.

 Bike Hire Included 

If you don’t own a suitable bike or would prefer to avoid bringing your own we have bike hire included in our holiday cost. These bikes are typically Scott Sportster hybrid bikes (or equivalent). 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. 

Travelling with Your Own Bike

The vast majority of airlines will charge you to transport your bike. This amount varies from carrier to carrier but we recommend always booking and paying for this in advance which will usually save you money compared to paying at the airport. Most airlines will also require your bike to be properly packaged for transport. Most commonly this will be in a bike bag or box specifically designed for the job. Please enquire directly with the airline for more information on their rules and regulations. There is a wealth of options when it comes to picking the right box or bag for your needs. 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.

Other Cycling Equipment

If you are taking your own bike, it is imperative that it is in good mechanical order. If you are not mechanically minded, we advise you to take your bike to a local bicycle dealer for a service before you travel. Details of which spares you should take will be included in the Information Pack sent with your booking confirmation.

Bring clothes suitable for cycling in – specific cycling kit if you have it or simply normal clothes comfortable enough for exercising. It’s also a good idea to bring bottles for drinking water, sunglasses, cycling gloves, a light but waterproof rain jacket and a fleece / sweater for mornings and evenings. It is also a good idea to bring shoes suitable for walking along with your cycling shoes. If you've got cycling shoes with cleats - bring your own pedals. A basic packing list will be sent to you with your booking confirmation.

Helmets

While riding with us it is compulsory that you wear a helmet. If you don’t have a helmet or don’t intend to bring your own we may, subject to availability, be able to provide one on request. You will not be permitted to ride unless you wear a helmet.

Vehicle Support

At strategic points (where access allows), you have the security of our support vehicle. In the vehicle there will be some space for tired bikers, allowing the chance of a well-earned break if needed. You will also be able to leave extra layers or spare kit here during the day meaning there is no need to carry any equipment other than that you would carry on a normal day ride.

Baggage allowance once you are in your destination

Once you reach your destination, your allowable baggage is one main piece of luggage per person other than your bike and a small day pack. Your main luggage should preferably be either a backpack / rucksack or ‘sports bag’ so as to assist in transportation between accommodations. The day pack may be useful for carrying your additional outer-layer clothing, camera and snacks (etc) while cycling. Please note this allowable baggage allowance is not your airline baggage allowance. Fees may apply for luggage depending on the airline. Please refer to the holiday booking page for further details on airline baggage charges.

Personal spending money

The local currency is the Euro. We suggest taking approximately €25 to €35 (per person excluding drinks) for those evening meals and lunches which are not included in the trip price. Any personal expenditure for things such as souvenirs depends very much on the individual. Outside of larger towns opportunities to draw money from an ATM or to exchange cash may be rare. Some places may accept card payments but it is better not to rely on this.

Travel Insurance

It is a condition of your trip that you are covered by a medical and personal accident insurance policy that includes repatriation to your home country and cover for all planned activities.

Weather

In Tuscany the climate varies from area to area. It is mainly influenced by the sea off the west coast of the region and also by the Apennine ridge which limits the territory to the north and to the east. On the plain, annual average temperatures are just a little lower than the average coastal temperatures. This is due to the increasing continental influence and the annual and daily thermal ranges. The average temperatures in January are generally between 4° C and 7° C/ 39.2-44.6°F, whereas in July they are generally between 28° C and 32° C/ 82.4-89.6°F.

Tuscany

Tuscany is a land of undulating green hills capped by medieval, tile-roofed towns and punctuated by cypresses, churches and stone farmhouses. En route you’ll find true archetypal Tuscan landscapes that look like waves of green, with barely a tree to lend it scale. Hidden in the folds are little farmhouses, but the main towns are all perched on the highest hilltops, as if bidding for the best view over the sea of fields. The surrounding areas are of great natural beauty, stunning narrow steep valleys, dense forests, spectacular eroded clay slopes (the ‘badlands’) and the vineyards of world-famous wines.

Holiday highlights

Siena

A self-contained and still part rural city that sits behind medieval walls. Siena's great attraction is its cityscape, a majestic Gothic ensemble that could be enjoyed without venturing into a single museum.

Pisa

Thanks to its extraordinary Leaning Tower and the impressive Campo dei Miracoli where it is situated, the university town of Pisa is one of Tuscany’s top attractions.  The historic centre has well-preserved Romanesque architecture and pleasing piazzas, where students and locals enjoy the city’s buzzing café and bar scene

Practical Information for this holiday

Group Size

In order to offer you as much choice as possible, we work with an expert partner for all cycling holidays. This is not an exclusive TD active Holidays tour. Your group will be made up of a range of travellers from different countries, who share in your passion for cycling. The group sizes are typically between 6 – 16 people.

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. Riding Colline Senesi, will prove the most challenging following a roller coaster route. 

Cycling Guides
TD active Holidays work with a local cycling partner in Italy, who have been running Cycling Holidays for over 20 years now. The expert team of guides are always on hand to make your holiday an unforgettable experience. Our guides in Italy come from all over the country and are immensely proud of their home. They enjoy helping others discover not just the best riding the country has to offer, but also the fantastic range of scenery, traditional food, and Italy’s unique culture and history. The local touch really helps to enhance your experience and helps you get the most from your time in Italy.  Your holiday will be led by 1 or 2 English speaking guides, depending on the size of the group. What places our guides head and shoulders above other cycle leaders is their focus on providing a great cycling experience and excellent customer service; from the very start to the very end of your holiday, you’ll be in safe hands. Our guides take care of all the daily planning and organisation, leaving you free to get on your bike and enjoy the ride
Accommodation
Accommodation will be a mixture of 3 and 4* hotels and agriturismi (local farmhouses)
Food

Italian breakfasts consist of bread and jams, sweet pastries and fruit, supplemented with cooked meats and cheese, yoghurt and cereals. On guided trips our guides pride themselves on their lunches and serve up a great buffet of fresh local treats often supplemented with a pasta dish to keep the legs turning. Evening meals are either taken at a local restaurant or your accommodation. Generally speaking these consist of antipasti (a selection of appetisers), a pasta course, a main course of meat or seasonal vegetables finished off with a sweet dish, fruit, coffee and liqueurs all washed down with the great local wine. Vegetarians and people with specific dietary requirements can be catered for – please indicate at the time of booking if you have any dietary requirements.

Preparation & training

In order to get the most out of your trip, you need to choose a holiday of the right grade and make sure you‘re prepared. The amount of preparation and training you need to do will depend on your own experience, your level of fitness and the type and grade of holiday you are going on.

 Bike Hire Included 

If you don’t own a suitable bike or would prefer to avoid bringing your own we have bike hire included in our holiday cost. These bikes are typically Scott Sportster hybrid bikes (or equivalent). 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. 

Travelling with Your Own Bike

The vast majority of airlines will charge you to transport your bike. This amount varies from carrier to carrier but we recommend always booking and paying for this in advance which will usually save you money compared to paying at the airport. Most airlines will also require your bike to be properly packaged for transport. Most commonly this will be in a bike bag or box specifically designed for the job. Please enquire directly with the airline for more information on their rules and regulations. There is a wealth of options when it comes to picking the right box or bag for your needs. 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.

Other Cycling Equipment

If you are taking your own bike, it is imperative that it is in good mechanical order. If you are not mechanically minded, we advise you to take your bike to a local bicycle dealer for a service before you travel. Details of which spares you should take will be included in the Information Pack sent with your booking confirmation.

Bring clothes suitable for cycling in – specific cycling kit if you have it or simply normal clothes comfortable enough for exercising. It’s also a good idea to bring bottles for drinking water, sunglasses, cycling gloves, a light but waterproof rain jacket and a fleece / sweater for mornings and evenings. It is also a good idea to bring shoes suitable for walking along with your cycling shoes. If you've got cycling shoes with cleats - bring your own pedals. A basic packing list will be sent to you with your booking confirmation.

Helmets

While riding with us it is compulsory that you wear a helmet. If you don’t have a helmet or don’t intend to bring your own we may, subject to availability, be able to provide one on request. You will not be permitted to ride unless you wear a helmet.

Vehicle Support

At strategic points (where access allows), you have the security of our support vehicle. In the vehicle there will be some space for tired bikers, allowing the chance of a well-earned break if needed. You will also be able to leave extra layers or spare kit here during the day meaning there is no need to carry any equipment other than that you would carry on a normal day ride.

Baggage allowance once you are in your destination

Once you reach your destination, your allowable baggage is one main piece of luggage per person other than your bike and a small day pack. Your main luggage should preferably be either a backpack / rucksack or ‘sports bag’ so as to assist in transportation between accommodations. The day pack may be useful for carrying your additional outer-layer clothing, camera and snacks (etc) while cycling. Please note this allowable baggage allowance is not your airline baggage allowance. Fees may apply for luggage depending on the airline. Please refer to the holiday booking page for further details on airline baggage charges.

Personal spending money

The local currency is the Euro. We suggest taking approximately €25 to €35 (per person excluding drinks) for those evening meals and lunches which are not included in the trip price. Any personal expenditure for things such as souvenirs depends very much on the individual. Outside of larger towns opportunities to draw money from an ATM or to exchange cash may be rare. Some places may accept card payments but it is better not to rely on this.

Travel Insurance

It is a condition of your trip that you are covered by a medical and personal accident insurance policy that includes repatriation to your home country and cover for all planned activities.

Weather

In Tuscany the climate varies from area to area. It is mainly influenced by the sea off the west coast of the region and also by the Apennine ridge which limits the territory to the north and to the east. On the plain, annual average temperatures are just a little lower than the average coastal temperatures. This is due to the increasing continental influence and the annual and daily thermal ranges. The average temperatures in January are generally between 4° C and 7° C/ 39.2-44.6°F, whereas in July they are generally between 28° C and 32° C/ 82.4-89.6°F.

Tuscany

Tuscany is a land of undulating green hills capped by medieval, tile-roofed towns and punctuated by cypresses, churches and stone farmhouses. En route you’ll find true archetypal Tuscan landscapes that look like waves of green, with barely a tree to lend it scale. Hidden in the folds are little farmhouses, but the main towns are all perched on the highest hilltops, as if bidding for the best view over the sea of fields. The surrounding areas are of great natural beauty, stunning narrow steep valleys, dense forests, spectacular eroded clay slopes (the ‘badlands’) and the vineyards of world-famous wines.

Trip Itinerary - Day by day

Day 1 – Travel to Tuscany

Full day

Travel to Tuscany

Begin your cycling holiday with a flight to Pisa. Upon arrival you will transfer with guide assistance to your hotel in Volterra. (Approximate transfer approx. 1.5 hours).

Overnight

Accommodation

1 night in Volterra

Day 2 - Volterra to San Gimignano - 40 kms

Full day

Volterra to San Gimignano - 40 kms

Today you will leave the walls of Volterra behind and embark on a breathtaking descent, riding past isolated farmhouses surrounded by green fields, between rows of olive trees and cypresses, becoming acquainted with just how beautiful this part of Italy really is. You will follow the Val D‘Elsa on a rolling road that will take you from rural countryside to a more mountainous area of dense forest. Cycle through 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. After lunch, the view will open up and you will 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 your guide will take you on a walk through its narrow streets – a great opportunity for your first Italian gelato. (Cycling distance: 40kms)

Overnight

Accommodation

1 night in San Gimignano

Day 3 - San Gimignano to Monteriggioni - 40 kms

Full day

San Gimignano to Monteriggioni - 40 kms

Today you will start heading south by bike, descending towards the plains of Colle Val d‘Elsa. You will 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 view from the top of the climb will hopefully outweigh the effort. Casole d‘Elsa is an authentic medieval town, far away from the tourists and clichés of Tuscany. You will 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 Monteriggioni, in an ancient medieval village, surrounded by vast vineyards; an ideal place to taste the local wines. (Cycling distance: 40kms)

Overnight

Accommodation

1 night in Monteriggioni

Day 4 - Monteriggioni to Buonconvento - 60 kms

Day 4 - Monteriggioni to Buonconvento - 60 kms

Full day

Today you 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 climb takes you up 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 you can discover Le Crete, the ‘badlands’ of Tuscany with classic scenes of rolling landscape lined with Cyprus trees. There will be a stop in the Etruscan hamlet of Murlo, yet another small stone fortified village, ideal for a coffee or ice cream break. Continue riding towards Buonconvento, your home for the evening. (Cycling distance: 40kms) Once you have freshened up, a short transfer will take us to the outskirts of Montalcino, where you will visit a family-run organic winery and enjoy a taste of Brunello wine overlooking the rolling hills. Dinner will be included this evening.

Full day

Accommodation

1 night in Buonconvento

Day 5 - Buonconvento to Asciano - 40 kms

Full day

Day 5 - Buonconvento to Asciano - 40 kms

After breakfast 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 to the famous 13th century monastery of Monte Oliveto Maggiore with its colourful frescos and botanical garden. After admiring the artwork and some lunch, you will continue along the winding road over vast open fields before your next stop at San Giovanni D‘Asso. Moving on you will 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. Dinner will be included this evening. (Cycling distance: 40kms)

Full day

Accommodation

1 night in Asciano

Day 6 - Asciano to Siena - 50 kms

Full day

Asciano to Siena - 50 kms

Today is your final day on your bike with Siena being your destination. You will 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, you will be on your way again, following a mix of tarmac and 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 to the Piazza del Campo where the famous Palio takes place. You can raise a glass to celebrate the end of your cycling efforts in one of the elegant bars overlooking this vibrant square. (Cycling distance: 40kms)

Overnight

Accommodation

1 night in Siena

Day 7 – Siena to Pisa

Full day

Siena to Pisa

Today you will transfer from Siena to the city of Pisa. (Approximate transfer time: 2 hours) You will have the day at leisure to explore this vibrant Italian city independently and at your leisure.

Overnight

Accommodation

1 night in Pisa

Day 8 – Return Home

Full day

Return Home

Today it will be time to say ciao to this beautiful part of Italy and transfer back to Pisa airport for your return flight home.

* Please note that the order of your excursions on the itinerary above is provisional and subject to change

Customer reviews

Hotel & accommodation available for this trip

Tuscany Cycling Holiday Accommodation Tourist Class

Accommodation during your Tuscany Cycling Holiday will usually be a mixture of 3 and 4 star hotels and “agriturismi” (local farmhouses). When you reach your accommodation for the evening, your bags and rooms will be waiting for you. Most breakfasts are continental style buffets. ... read more read more read more

Accommodation during your Tuscany Cycling Holiday will usually be a mixture of 3 and 4 star hotels and “agriturismi” (local farmhouses). When you reach your accommodation for the evening, your bags and rooms will be waiting for you. Most breakfasts are continental style buffets. Picnics will be provided en route for lunch, and dinner can be taken at your leisure and own expense at the hotel or at a local restaurant. The exact accommodation arrangements for your holiday will be advised with your final documents approximately 10 days before departure.  

Hotel address
Tuscany Cycling Holiday Accommodation



View available dates for this hotel

* Some hotel facilities may be seasonally operated or under maintenance and therefore unavailable at the time of your stay. Charges may apply for certain facilities.

View more hotels

Departure Dates & Prices

Find your perfect holiday...

  • Date
  • Departs
  • Duration
  • Hotel & Accommodation
  • Price
  •  
Filter your results
Filter your results
View more departure dates

Departing on
Change date

Hotels on this trip

View all hotels

What's included in your price

inc. all taxes & charges

Price, taxes, flight times & availability are subject to change. E&OE. Price based on per person, sharing. Single Supplement cost may apply.

How many people are travelling?
Book now
  • Single Supplement from €149.00
  • Baggage from €40.00
  • Insurance from €12.50

Peace of Mind with TD active Holidays

Why us?

  • We’ve done the research for you, creating perfectly planned itineraries
  • Flights, transfers, accommodation and excursions included in nearly all our tours
  • We are experienced and dedicated to your experience
  • No holiday surcharges – guaranteed

Our Guides

  • Friendly and welcoming everywhere you go
  • Local experts, passionate about their area
  • Take pride in making your holiday memorable
  • Innovative itineraries with amazing excursions

Our Promise

  • To remember your holiday is a very precious time
  • To go the extra mile for you, our customers
  • To describe our holidays in an honest manner
  • To use your feedback to continually improve our service

Fully Protected

  • 24/7 emergency contact number while abroad
  • We are a privately owned business and have been around for over 20 years
  • Licenced by the Commission for Aviation Regulation, TO 163 & TA 0692