Jump to content
Jump to footer
Book now
To the online version
Two cyclists surrounded by vineyards, rolling hills and cypresses

Tuscany with Charm

Sense of life between Italy's hills

8 Days / 7 Nights
Athletic
179  kg
CO₂-Emissions are offset
Two cyclists surrounded by vineyards, rolling hills and cypresses

Experience and cycle the beauty of Tuscany in eight days. This tour is one of our sporty tours, which means you cycle a lot, but you also see a lot more. The unique landscape will literally carry you and you will be warmly welcomed in the characteristic villages. In addition, there is art, cuisine and cities that are among the most beautiful in the world: Pisa, Florence and Siena! Buon Viaggio!

The very first stage from Montecatini Terme leads to a cultural site of the world - Vinci is, as the name suggests, the birthplace of Leonardo da Vinci. Here you will already be immersed in this unique region, dotted with olive groves, vineyards, castles and picturesque villages.

On the way to Pisa, you will pass Lucca, an insider's tip among the cities of Tuscany, and the lake of Massaciuccoli, which was described as a paradise by Puccini. On day 5, the route leads to San Gimignano, the "city of towers". These striking buildings represent the noble families that once resided here. Siena and Florence form the fitting "grande finale" of the tour - immerse yourself in the historic old towns with their numerous architectural masterpieces.

  • The museum of the genius Leonardo da Vinci: Welcome to the Renaissance! The birthplace of one of Tuscany's most famous sons dedicates a museum to him with countless of his sketches, models and replicas of his works. Only a few kilometres away is the "Casa Natale di Leonardo" - his birthplace. This is also definitely worth a visit!
  • Cycling across the Piazza dei Miracoli in Pisa: When you think of Pisa, the first thing that comes to mind is usually the Leaning Tower. Rightly so, because it is an eye-catcher. But the Cathedral, the Baptistery and the Botanical Garden are also real highlights.
  • The breathtaking Tuscan hills: Vast fields, olive groves, orchards full of juicy peaches and the medieval history characterise the Tuscan landscape. Every now and then, the hills offer a view of the sea or the picturesque Arno River, which shaped the region as a trade route. Fantastic!
  • The Chianti wine region: If you indulge in wine tasting, then definitely here - the wines of Tuscany are drunk all over the world due to their high quality. In Castellina and Greve (day 7) you can follow in the footsteps of first-class winegrowing.

The stages are not excessive, mostly around 55 km in length, but Tuscany is a hilly area, which adds to the level of this tour. The longest stage on day 3 can be shortened by taking a train ride at your leisure.

On our ‘Cycle Tours with Charm’ you can enjoy the full service of our individual active holidays while staying in very special accommodation with that extra something in the best location. That means you can look forward to luxury furnishings and decor in the local style, as well as cuisine at the highest level. Many of our hotels with charm also offer large pools and a wellness area where you can relax after a lovely day of cycling.

  •  
Book now
To the online version
Two cyclists surrounded by vineyards, rolling hills and cypresses

Tuscany with Charm

Sense of life between Italy's hills

8 Days / 7 Nights
Athletic
179  kg
CO₂-Emissions are offset
Two cyclists surrounded by vineyards, rolling hills and cypresses

A plate of pasta paired with a glass of Chianti — a classic scene that could open any film about Italy. On a cycling tour through Tuscany, it’s simply part of everyday life. What truly captivates are the stunning landscapes, charming villages, historic towns, and the carefully chosen accommodations where you’ll stay on our delightful journeys. Your adventure begins in the spa town of Montecatini Terme, from where you’ll pedal through endless vineyards, scenic olive groves, and gently rolling hills. Along the way, you’ll visit world-renowned cities like Florence, Siena, and Pisa. Equally enchanting, though less famous, are the wine village Castellina in Chianti and San Gimignano, the iconic town of towers.

The very first stage from Montecatini Terme leads to a cultural site of the world - Vinci is, as the name suggests, the birthplace of Leonardo da Vinci. Here you will already be immersed in this unique region, dotted with olive groves, vineyards, castles and picturesque villages.

On the way to Pisa, you will pass Lucca, an insider's tip among the cities of Tuscany, and the lake of Massaciuccoli, which was described as a paradise by Puccini. On day 5, the route leads to San Gimignano, the "city of towers". These striking buildings represent the noble families that once resided here. Siena and Florence form the fitting "grande finale" of the tour - immerse yourself in the historic old towns with their numerous architectural masterpieces.

  • The museum of the genius Leonardo da Vinci: Welcome to the Renaissance! The birthplace of one of Tuscany's most famous sons dedicates a museum to him with countless of his sketches, models and replicas of his works. Only a few kilometres away is the "Casa Natale di Leonardo" - his birthplace. This is also definitely worth a visit!
  • Cycling across the Piazza dei Miracoli in Pisa: When you think of Pisa, the first thing that comes to mind is usually the Leaning Tower. Rightly so, because it is an eye-catcher. But the Cathedral, the Baptistery and the Botanical Garden are also real highlights.
  • The breathtaking Tuscan hills: Vast fields, olive groves, orchards full of juicy peaches and the medieval history characterise the Tuscan landscape. Every now and then, the hills offer a view of the sea or the picturesque Arno River, which shaped the region as a trade route. Fantastic!
  • The Chianti wine region: If you indulge in wine tasting, then definitely here - the wines of Tuscany are drunk all over the world due to their high quality. In Castellina and Greve (day 7) you can follow in the footsteps of first-class winegrowing.

The stages are not excessive, mostly around 55 km in length, but Tuscany is a hilly area, which adds to the level of this tour. The longest stage on day 3 can be shortened by taking a train ride at your leisure.

On our ‘Cycle Tours with Charm’ you can enjoy the full service of our individual active holidays while staying in very special accommodation with that extra something in the best location. That means you can look forward to luxury furnishings and decor in the local style, as well as cuisine at the highest level. Many of our hotels with charm also offer large pools and a wellness area where you can relax after a lovely day of cycling.

  •  

Itinerary at a glance

San Gimignano is known as the city of towers, and in Siena the cityscape is enchanting. Along the Arno, you cycle through peach orchards and olive groves, now and then a view of the sea opens up. Be sure to try the Chianti!

In the hotel, you will first get detailed information on the tour and your bikes. Afterwards, we recommend taking a walk in the spa park or taking the historical rack railway train to Montecatini Alto.

At the beginning of your tour, you will cycle through the vast plains of the valley Valdenievole, which is characterized by a lot of agriculture. You will continue through the first Tuscan villages, through olive groves to Vinci, the birthplace of Leonardo. We recommend visiting the museum in the castle since it is home to one of the largest and most original collections of machines and models of the inventor. Then, you will take quiet roads back to Montecatini Terme.

On your way to Lucca, you will pass the small, medieval wine town of Monte Carlo, where one of the few white wines of Tuscany flourishes. (Alternatively, you can take the train to Lucca). A bike ride on the historic city walls offers magnificent views of churches and towers that rise above the countless roofs of the city. Afterwards, you will continue to Lake Massacciuccoli, also called Lake of Giacomo Puccini with stunning views of the sea and Pisa with its Court of Miracles, the Piazza dei Miracoli with its Leaning Tower.

First, the bike path leads you along the river Arno. Many fertile fields line your way and you will continue your tour through the Pisan hills, on whose gentle slopes sweet wines, olives and juicy peaches grow. You will see small medieval villages located on the hilltops and soon you will have reached today’s destination, the spa town Casciana Terme.

Today, you will cycle on beautiful trails through vineyards and rolling hills to San Gimignano. On your way, you will see images of the original Tuscany as they have been painted many times. Just before you reach today’s destination, the silhouettes of the famous medieval towers appear in front of you. Each aristocratic family once had their own tower here – and these towers still dominate the townscape.

The beautiful Tuscan landscape on today‘s stage makes you forget the small climbs on the route. Once you reach the small fortified village of Monteriggioni, you will feel as if you were in the Middle Ages. Today’s highlight undoubtedly is the architectonic paradise of Siena.

The tour takes you into the midst of the wide Chianti region. Only here the world-renowned “Chianti Classico” wine, which is much respected among wine connoisseurs, is grown. The charming wine village of Castellina is on your way to Greve. Thanks to its famous wine and olive production, it is called the capital of the Chianti region. From here you will get back to Florence by public bus (bike drop-off in Greve)

Afterwards: individual departure, extension of your trip, or combination with the tours “Venice-Florence” and “Florence-Rome”.

Itinerary at a glance

In San Gimignano, medieval towers rise proudly—one for each noble family. Florence, with its countless bridges, and Pisa, famed for its iconic leaning tower, are sure to captivate you. As you cycle along the Arno River, you’ll pass through fragrant peach orchards and sprawling olive groves, with occasional glimpses of the sea. Italy’s culinary treasures await, too: over antipasti, pizza, and pasta, you’ll easily strike up conversations with locals. And be sure to savor a glass of the renowned Chianti!

Tour briefing and bike handover. Take your time to explore the surroundings before you hop in the saddle the next day. A leisurely stroll through the famous spa town is a perfect start—or perhaps a ride on the funicular up to Montecatini Alto?

The small medieval wine town of Montecarlo—where one of Tuscany’s rare white wines flourishes—lies along the route to Lucca (alternatively, you can reach Montecarlo independently by train). Cycling atop its nearly fully preserved city walls offers an unforgettable experience. The journey then continues to Lake Massacciuccoli, also known as Giacomo Puccini’s lake, boasting breathtaking views all the way to the sea and Pisa’s “Piazza dei Miracoli,” home to the world-famous Leaning Tower.

The cycling route first follows the Arno River, accompanied by fertile fields. Next, you’ll pass through the hills of the Pisa region, where gentle slopes are dotted with sweet vineyards, juicy olives, and ripe peaches. Small medieval villages cling to the hilltops like swallows’ nests. With these enchanting sights, you’ll soon arrive at today’s destination, the spa town of Casciana Terme.

You’ll pedal through vineyards and softly rolling hills along picturesque paths toward San Gimignano, surrounded by the timeless beauty of the authentic Tuscan countryside. Just before you arrive, the iconic silhouette of the world-famous medieval towers will come into view. Once owned by noble families, these historic towers still define the town’s charming skyline today.

The stunning Tuscan landscape along today’s route makes the occasional small climb barely noticeable. By the time you reach the fortified village of Monteriggioni, you’ll feel transported back to the Middle Ages. But the undeniable highlight of the day is the architectural gem that is Siena.

Enjoy great views over the vineyards on a beautiful mountain road. Take a break in the stone village of Vagliali and enjoy a good Italian cappuccino before cycling along a white road through vineyards and deciduous forests to Radda. Fortify yourself for lunch with a typical plate of pasta and savour the atmosphere of this village gem before the tour continues into the heart of Chianti to Castellina.

The last day of cycling takes you over a plateau with great views and then hilly to Greve with its enchanting old town centre. The capital of Tuscany draws ever closer and you cycle comfortably on a long descent to the Ponte Vecchio. You are sure to have found your favourite Tuscan wine this week. Treat yourself to it again at the end of your trip in beautiful Florence.

Flexible departure options, extensions, or combination with “Florence to Rome” tours are all available.

Other variations of this tour

Difficulty level

Athletic

Tuscany has a wonderful but also hilly landscape. You will cycle on quiet minor roads and sometimes even on country lanes from one famous city to another. Close to bigger cities, traffic is unfortunately unavoidable.      

Difficulty level

Athletic

Tuscany is a breathtaking yet hilly region. Good fitness or an e-bike will help you tackle the daily climbs with ease. The stages lead you along charming country roads and quiet paths from one famous town to the next. While you may encounter heavier traffic when entering or leaving towns, much of the route offers peaceful stretches where you can fully immerse yourself in the beauty of Tuscany.

Prices & Dates

 

 

Prices per person in EUR

Sustainably on the go

Our contribution to climate protection

179 kg
CO₂-Emissions are offset
With a cycling holiday, you are opting for an extremely climate-friendly form of travel. We are aware that even this generates a certain amount of CO2 emissions, even if this is low compared to other forms of travel. The emissions caused are calculated per travel and person using the internationally recognised ‘Carmacal’ CO2 calculator and offset by supporting carefully selected climate protection projects. A detailed overview of emissions in the areas of transport, accommodation, activities and on-site catering can be found here.
Accommodation (56%)
Meals (18%)
Transport (26%)
Activities (1%)
100%

Our rental bikes

Eurobike unisex rental bike with 21/24 gears
Unisex bike 21/24-speed
Dereilleur gears with freewheel

High-quality unisex touring bike with comfortable low entry

Body size approx. 148 cm - 190 cm

43 cm |
46 cm |
51 cm |
56 cm
Eurobike Men's Rental Bike with 21 gears
Men's bike 21-speed
Dereilleur gears with freewheel

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

Body size approx. 165 cm - 205 cm

56-51 "sloping" cm |
60 cm |
64 cm
Eurobike Rental Bike PLUS
Rental Bike PLUS 20/27-speed
Dereilleur gears with freewheel

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

Body size approx. 155 cm - 205 cm

46 cm |
50 cm |
51 cm |
55 cm |
60 cm |
63 cm
Eurobike e-bike rental from KTM
Unisex Electric Bike 8-speed
Hub gears

High-quality unisex electric bike with comfortable low entry

Body size approx. 148 cm - 195 cm

46 cm "xs" |
46 cm |
51 cm |
56 cm

Services and Information

Further details about this tour

Included

  • Accommodation in hotels with charm
  • Breakfast
  • Welcome briefing (German, English)
  • Luggage transfer
  • EUROBIKE developed route
  • Detailed travel documents 1x per room (German, English, French)
  • 1 bus transfer from Greve – Florence incl. your bike
  • App for Navigation and GPS-data
  • Service hotline

Optional

  • Bike rental, including rental bike insurance
  • Private bikes can be brought directly from Greve to Florence or Montecatini Terme for no extra charge.
  • Return transfer by minibus to Montecatini Terme, costs EUR 55 per person, reservation necessary, to be paid in advance

Arrival / Parking / Departure

  • Montecatini Terme central train station
  • Florence or Pisa airport
  • Hotel parking garage, costs approx. EUR 105 per week
  • Public parking spaces in the blue zone costs approx. EUR 5 per day
  • Good train connections from Florence to Montecatini Terme

Things to note

  • Tourist tax, if due, is not included in the price!
  • Further important information according to the package travel law can be found here!

Join us in achieving greater sustainability by choosing our digital route book, rather than the printed version. As a small thank you we will give you a discount of €20 per room.

Services and Information

Further details about this tour

Included

  • Accommodation in hotels with charm
  • Breakfast
  • Welcome briefing
  • Luggage transfer
  • Digital travel documents incl. navigation app, GPS-data, route book
  • Service hotline

Optional

  • Printed route book, per room EUR 20
  • Bike rental, including rental bike insurance.
  • Return transfer from Florence to Montecatini Terme every Saturday, costs EUR 65 per person, reservation necessary, to be paid in advance

Arrival / Parking / Departure

  • Arrival by train to Montecatini Terme
  • Florence or Pisa airport
  • Parking: hotel parking spaces, costs approx. EUR 10 to EUR 15 per day, free public parking spaces resp. blue zone
  • Departure by train from Florence to Montecatini Terme, duration approx. 1 hour

Things to note

  • Tourist tax, if due, is not included in the price!
  • Further important information according to the package travel law can be found here!

Our Hotels

Relax in our charming accommodations along your cycling tour

Travel stories for this tour

Personally on site for you

Sarah Salzlechner

"We look forward to making your holiday dreams come true"

Sarah Salzlechner
Travel Specialist
One call to vacation bliss
Monday - Friday: 09:00 AM - 06:00 PM
Call now
One click to vacation bliss
 
I am looking forward to your message!
Contact form

4.75 out of 5 stars

12 ratings
5
75%
4
25%
3
0%
2
0%
1
0%
Load more

Other tours that might interest you

from
€1,499
Book now Book
Our top tours for 2026 are online!
Discover now & book
/en/cycling-holidays/2026

Are you ready for the 2026 cycling season? Discover exciting travel ideas - this is where travel dreams come true. Don't forget: Book by February 28 and secure our early booking bonus!

Discover now & book
2026
Three cyclists cycle past the Drachenwand rock formation on Lake Mondsee.
You now receive special conditions when you book a trip.