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Group of cyclists on road with medieval Tuscan hilltop village in background, featuring stone towers and traditional buildings under blue sky.

Cycling in Tuscany - The classic route

The sweet life in the hills of Tuscany

8 Days / 7 Nights
Moderate
Group of cyclists on road with medieval Tuscan hilltop village in background, featuring stone towers and traditional buildings under blue sky.

The essentials at a glance

Self-guided cycling tour through Tuscany's rolling hills and historic towns. The route covers approximately 325 km over 6 cycling days, passing through Montecatini Terme, Lucca, Pisa, Casciana Terme, San Gimignano, Siena, Chianti region, and Florence. Cycle along quiet country roads through vineyards, olive groves, and medieval villages. Moderate difficulty with some climbs rewarded by panoramic views. Includes accommodation, breakfast, bike rental, luggage transport, and GPS navigation.

“La vita è bella!” – and Tuscany certainly knows how to celebrate the good life. Your cycling journey leads through rolling countryside filled with vineyards, cypress-lined roads, historic towns and remarkable cultural landmarks. Discover the legacy of Leonardo da Vinci in Vinci, cycle past Pisa’s famous Leaning Tower and cross the Ponte Vecchio in magnificent Florence.

The pleasures continue after you leave the saddle. Tuscan cuisine offers everything from flavourful antipasti to sweet zabaione, while the wines produced in the vineyards along your route provide the perfect accompaniment. With its unique blend of beautiful landscapes, celebrated gastronomy, art and architecture, Tuscany creates a cycling experience that is difficult to match.

 

Highlights on this tour

  • Lucca with the great views of the city while biking on the historic city walls 
  • Pisa and its famous Leaning Tower 
  • The town of the famous white wine - Monte Carlo and the Chianti Classico region at Greve 
  • Discover several of the  characteristic spa towns along the way 
  • Cycling through the vineyards and rolling hills in the unique Tuscan terrain 

The route

Tuscany captivates with its rolling hills and picturesque landscapes. As you cycle between historic towns, the route takes you along quiet country roads and scenic paths through the beautiful countryside. A few climbs await along the way, but the magnificent panoramic views make every pedal stroke worthwhile. Please be aware that traffic may be heavier when entering and leaving the towns.

Itinerary

See the day-by-day itinerary below.

Begin your stay in Montecatini Terme, one of Tuscany’s most renowned spa towns. Take time to explore its impressive thermal buildings, beautifully maintained gardens, elegant squares and vibrant streets. Don’t miss the historic funicular railway to the picturesque hilltop village of Montecatini Alto, where wonderful views across the surrounding landscape await.

Category A - Hotel (example): Grand Hotel Croce di Malta
Category B - Hotel (example): Hotel Manzoni

Charm: Grand Hotel Croce di Malta

On the way to Lucca, you pass through the small medieval wine town of Montecarlo, known for producing one of Tuscany’s few white wines. In Lucca, you can cycle along the city’s almost completely intact Renaissance walls – a truly memorable experience. The route then leads towards Lake Massaciuccoli, closely associated with composer Giacomo Puccini. Along the way, magnificent views extend towards the coast and Pisa’s Piazza dei Miracoli, where the iconic Leaning Tower awaits.

Category A - Hotel (example): Hotel Repubblica Marinara
Category B - Hotel (example): Hotel Soggiorno Athena
Charm: Hotel Bologna

The day begins with a relaxing ride along the Arno River, passing through a landscape of fertile farmland. The route then leads into the rolling hills surrounding Pisa, where vineyards, olive groves and peach orchards cover the gentle slopes. Along the way, picturesque medieval villages appear high above the countryside before you reach the welcoming spa town of Casciana Terme.

Category A - Hotel (example): Albergo Roma
Category B - Hotel (example): Albergo Stella
Charm: Agriturismo Le Valli

Today’s route winds through vineyards and gently undulating hills as you cycle towards San Gimignano, surrounded by the classic scenery of rural Tuscany. As you approach the town, its famous medieval towers gradually rise above the landscape. Originally built by wealthy and influential families as symbols of prestige and power, they continue to shape San Gimignano’s distinctive skyline.

Category A - Hotel (example): Hotel San Michele
Category B - Hotel (example): Albergo Le Colline
Charm: Hotel La Cisterna

The beauty of the Tuscan countryside provides a wonderful backdrop for today’s ride and makes the few gentle climbs feel well worth the effort. When you arrive at the walled village of Monteriggioni, its remarkably preserved medieval atmosphere feels like stepping back in time. The day’s greatest highlight, however, is Siena, a magnificent city filled with outstanding architecture and historic charm.

Category A - Hotel (example): Hotel Italia
Category B - Hotel (example): Hotel Italia
Charm: Hotel Villa Ermellina Siena

Cycle along a scenic hillside road with sweeping views across the surrounding vineyards. Pause in the stone-built village of Vagliagli for a classic Italian cappuccino before continuing along one of Tuscany’s characteristic white gravel roads through vineyards and leafy woodland to Radda. Enjoy a traditional pasta lunch and soak up the atmosphere of this charming village before riding deeper into the heart of Chianti towards Castellina.

Category A - Hotel (example): Hotel Villa Godenano
Category B - Hotel (example): Il Colombaio
Charm: Palazzo Squarcialupi Castellina

Your final cycling stage begins across an elevated plateau with far-reaching views before continuing through the hills to Greve and its atmospheric historic centre. From here, Florence gradually draws closer, and a long, pleasant descent leads you towards the famous Ponte Vecchio. After a week among Tuscany’s vineyards, you may already have discovered a favourite local wine – and beautiful Florence is the perfect place to raise a final glass to your journey.

Category A - Hotel (example): De la Pace
Category B - Hotel (example): Hotel Grifone
Charm: C Hotels

After breakfast you will be checking out of the hotel for departure.

Prices and dates

Prices per person in EUR

Price includes

ACCOMMODATION

  • 7 nights at hotels in the selected category

 

FOOD & DRINKS

  • Breakfast every day

 

CYCLING & EXPERIENCES

  • 6 days of cycling (approx. 325 km in total)
  • Welcome meeting and briefing
  • Rental of standard bicycle (can be deselected – see details below)
  • Detailed descriptions of the carefully selected routes (route maps, route descriptions, information about relevant tourist attractions and important phone numbers – in English)
  • Access to the route in our GPS app, which also works offline (one access per person)
  • Possibility of GPX files for use in your own GPS

TRANSPORT

  • Luggage transport between the hotels

 

OTHER

GENERAL

  • Transport to/from Italy
  • Handling fee (€ 25)
  • Travel insurance

 

REQUIRED AND PAID LOCALLY

  • Possible tourist taxes at the hotels

OPTIONAL
The following can be selected in the booking form, when you book the tour.

  • Upgrade to E-bike (selected when booking the tour)

 

Use the button "Calculate price" on this page to see what the tour will cost with your wanted inclusions.

PARKING
It is possible to park at the first hotel or nearby. Parking cannot be reserved in advance and must be arranged directly with the hotel (expect a cost of approximately €10–20 per day).

 

Bikes

You can choose from these bikes on the tour.
Red unisex touring bicycle with 21-speed gearing, equipped with bright yellow panniers on front and rear, parked on grass.
Unisex 21-speed bike
Dereilleur gears with freewheel

High-quality unisex touring bike with comfortable low entry.

Body size approx. 148cm - 190cm.

43cm
46cm
51cm
56cm
Red men's touring bicycle with 21 gears parked on grass. Features yellow panniers on rear rack and handlebar bag, black saddle and grips.
21-gear men's bike
Dereilleur gears with freewheel

High quality men's touring bike with classic diamond frame.

Body size approx. 165cm - 205cm.

56-51 "sloping" cm
60cm
64cm
Dark gray touring bicycle with rear rack, front suspension, and multiple gears parked on vibrant green grass beside a paved path.
PLUS men's bike 27-gear
Dereilleur gears with freewheel

Sportier, lighter and more precise premium rental bike with diamond frame.

Body size approx. 155cm - 205cm.

46cm
50cm
51cm
55cm
60cm
63cm
Red electric bicycle with yellow panniers parked on green grass. The e-bike has a front basket and rear pannier bag, both in bright yellow.
Unisex 8-speed E-bike
Hub gears with freewheel

High quality unisex e-bike with comfortable low entry.

Body size approx. 148cm - 195cm.

46cm "XS"
46cm
51cm
56cm

Practical information

Here you can get answers to various questions about the trip
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The price is based upon two people sharing. It is also possible travel alone in a single room. Simply choose "1 person" in the booking form and it will automatically add the single room surcharge.

On this tour you will be on your own supplied with maps, route descriptions and luggage transfers. That means that your time is your own and you have plenty of time to enjoy the stages in your own pace.

 

Check the price quickly
You can quickly check the price of your desired trip without having to fill out any forms. Here’s how:

  1. Click on the "Calculate Price" button (you’ll find it in the "Dates and Prices" section) – this will take you to the first pages of the booking form
  2. Select your preferred date, number of people, room distribution, any extra nights, and any available add-ons you may want
  3. See the price


Get a quote
If you would like a flight included, or changes made to the trip, you can request a customized offer by clicking the "Get Quote" button at the top of the page. Remember to describe in detail what changes you would like.

The booking process
When you book the trip, we will begin booking hotels and arranging all the practical aspects of your tour. This process typically takes 5–8 working days, but in some cases it may take longer for certain bookings. If you arrange your own transportation, we recommend waiting until we have confirmed your booking before making any arrangements.

Dates
If you can select a date in the trip calendar (in the booking form), then this is a possible start date. We regularly update our trips with sold-out dates; these dates will then appear in red/grey and cannot be selected.

On all our cycling holidays it is possible bring your own bike but it also possible to rent a bike for the tour. The bikes you can rent are all perfectly suited for the tour and the local terrain and all bikes are perfectly maintained. If you want to rent a bike on your holiday, then you select this on the booking form.

Equipment included in the bike rental:

  • Saddle bag (water repellent)
  • Handlebar bag (water repellent)
  • Service-set with tools and extra bicycle tube
  • Combination lock

Please note that helmets are not included and you need to bring your own.

Roadside assistance
All bikes are equipped with puncture resistant tyres which means that it is virtually impossible to puncture. No rule without exceptions, so should you experience a punctured tyre then you can quickly fix it by using the tools in the service-set. If the damage is greater than a simply puncture then you simply call us and we make sure that your bike is fixed or you will be supplied with a new bike as quickly as possible.

Insurance is included
Insurance against theft and damages are included in the bike rental. Should you have any problems of this nature then all you have to do is to let us know and we will supply a new bike as quickly as possible. Naturally, careless or mischievous behavior is exempt from this.  

The flights to/from Pisa are not included in the price. You can easily find a suitable flight via a flight booking engine such as Momondo or Skyscanner.

Notice: we recommend that you book with us and wait for the confirmation before you book your flights.

Get a quote
If you prefer that we handle your flight, then we would be happy to arrange this for you. You simply book a quote below the map on this page and we will return with a quote as soon as possible (usually within 2-5 working days). Please note that we add a handling fee of 45 euro to each flight and this means that the flight will be cheaper if you book it yourself.

On this tour you can select between three different hotel categories:

Charme: Carefully selected extra good hotels
Category A: 3- and 4-star hotels, some with swimmingpool
Category B: 3-star hotels

You can select your desired category on the booking form.

Breakfast is included every day. It is very easy to find both lunch and dinner in the cities you pass or stay in, through out the trip.

Luggage transfer is included on this tour. Upon arrival at the first hotel you will be given luggage tags along with the rest of the welcome package. You fill out the luggage tags and put them on your bags where they will remain for the duration of the tour.

Your luggage is picked up from the hotel lobby around 9am every morning and will arrive at your next hotel at 6pm at the latest (often long before that). If there are any special exceptions to the luggage transfer you will be notified upon arrival.

Luggage transfer includes one bag per guest and the bags can weigh 20kg each.

On this tour, you will receive the following documents:

Upon booking
Immediately after booking this trip, you'll recieve a pre-booking-email where you can get a complete overview of your booking. Once the tour is confirmed you get a confirmation email from us along with practical information about the tour.

One month before departure
You will receive a hotel list and final travel documents.

Upon arrival at the first hotel
You'll receive the welcome pack, which contains everything you need for the trip. There will be route descriptions, maps, luggage tags, specific local vouchers and if you have rented a bike, they will also be handed out at the first hotel. The documents are in English.
Notice: On some tours it is necessary to either print the documents yourself or to bring them electronically.

There will be an information meeting conducted by one of our local partners, where bikes will also be distributed and adjusted. You will meet in the reception area unless you are informed otherwise during check-in.

This journey has a difficulty level of 2-3, which means that most days on the tour are grade 2 and a few are grade 3.

Grade 2
For cyclists who like hilly terrain and a bit longer distances. You cycle on good roads, which usually don’t have much traffic. The distance is between 35 – 60 km or 20 – 38 miles. If you are capable of riding a bike and you have a normal good health, you should not worry to join these trips.

Grade 3
Longer distances in hilly terrain, often with steep climbs. The distance is usually 65 – 80 km or 40 – 50 miles per day. Requires good shape and health. We highly recommend that you practice on some longer rides before you leave home.

See more about trip gradings for cylcing holidays 

After booking this trip, you get access to various discount schemes.

We recommend taking out travel insurance that covers at least illness, accident, repatriation, lost holiday, luggage and liability. As a customer, you are responsible for taking out the necessary travel insurance to cover these costs.

Before taking out insurance, you should check whether you are already covered by travel or cancellation insurance through your home insurance company, credit card or similar - please note that there may be differences in insurance coverage.

A cycling holiday in Tuscany, from Montecatini Terme to Florence, offers various climatic experiences. In spring (March to May), temperatures range between 10-20°C with sunny days and occasional showers. High summer (July to August) is hot, 25-35°C, with almost no rain, so it’s important to start early and drink plenty of water. Autumn (September and October) has pleasant temperatures of 15-25°C at the beginning and cooler weather later. The landscape is beautiful at this time with autumn colors. Layered clothing, sun protection, and a good bike are necessary to fully enjoy the trip. There is most rain in spring (March to May) and autumn (September to October) in Tuscany. During these periods, frequent showers can occur, while summer is typically dry and sunny.

Join the special ‘Bering Cycling Holidays’ group on Facebook. Here you'll be notified about new holidays, special offers and much more.

Link to the group

Note: you need to request membership, but everyone is approved.

When you book a trip with us, we plant a tree in Kenya.

Bering Travel partners with Growing Trees Network, which has been planting trees in Kenya since 2020 in collaboration with Seniorer uden Grænser (Seniors Without Borders). The trees are planted with small-scale local farmers in the Mount Kenya region, as well as at schools, where the fruit helps supplement students’ diets and is incorporated into their learning.

The trees are planted using the shamba method – a sustainable approach that combines reforestation with agricultural crops. This keeps the soil covered with vegetation throughout the year, helping to prevent nutrient loss and reduce erosion.

The contribution to tree planting comes directly from Bering Travel’s own earnings and is not added to the price of your trip.

This initiative is not intended as a carbon offset for travel, but as a way to make a positive contribution.

Read more

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