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7 days
  • self guided cycle
  • 6 nights in 3-4 star hotels
  • 6 Breakfasts





Trip Code: TCV

Trip highlights

  • Cycling through classic Tuscan landscape of rolling hills, vineyards, olive groves and quintessential hill top towns
  • Exploring the renowned cities of Pisa, Siena and Florence
  • Enjoying the superb wines of the Chianti region
  • Discovering the towers of San Gimignano and the thermal waters of Casicana Terme

Tuscany needs little introduction, having been the holiday destination of choice for centuries. Cycling through this classic Tuscan landscape of rolling hills interspersed with verdant vineyards and cypress trees lining the roads is one of life's great pleasures. Culture, history and excellent cuisine is ever present as you pedal between towns. From Pisa and its leaning tower, pass through medieval Siena, along a route of vineyards all the way to Florence, the cradle of Renaissance. At night soak up the atmosphere in piazza's and trattoria's and join the passegiata, an evening stroll often accompanied by a gelato.

Trip Grading

moderate to challenging

More info about grading system

Make your own arrival to Pisa, the city famous for its magical Piazza dei Miracoli (Square of Miracles) with the characteristic Leaning Tower. UNESCO World Heritage since 1987, Pisa has a large number of monuments as well as the friendly and lively atmosphere of a university city.

Meals:  Nil

The cycle route begins along the river Arno where you soon reach Pontedera, a rather modernized district, home to the wine company Castellani, and a sweets factory called Amedei. Continue through olive groves and vineyards, features you will pass by alot on this inspiring journey. Finally you will reach the thermal town Casciana Terme, famous for its Etruscan roots, where thermal water was discovered by 12th century Countess Matilda of Tuscany.

Meals:  B

Following the Via Francigena through vineyards and rolling hills you will arrive at San Gimignano, a hilltop village offering medieval landscapes. This UNESCO awarded walled hamlet is known for its many towers. And in the evening, treat yourself with the local exquisite cuisine!

Meals:  B

By following the centuries old Via Francigena, you'll be welcomed by the views of Mount Maggio and the castle of Monteriggioni, Dante's subject in his famous literary pieces. Siena, a superb medieval town, is just ahead; you'll recognise it by the historic brick buildings and the crown of Torre del Mangia. Take time to sit in Piazza del Campo, where the famous Palio di Siena horse race takes place each year in July and August.

Meals:  B

Today's first stop is Castagnolli, where you will admire the Brolio Castle, home to the Ricasoli family and today a well-managed wine cellar, too. Then you reach Radda in Chianti, a classic Chianti village nestled inside the verdant hill region, among remnants of the Etruscan age, and Panzano, a lush green district with a countryside charm. Greve in Chianti is up next where the famous Chianti Classico Wine Festival is held every year in September. A sip of the local wine will fire up your senses.

Meals:  B

A shorter cycle day today with free time on arrival to explore one of the world's most beautiful cities. The first let is to a small town called Mercatale, where you will be given wine-tasting opportunities from its local wine cellars. After ten kilometres detour to Impruneta, a neighbouring district filled with terracotta art. Back on your saddle, Florence is waiting for you! We recommend not missing the Duomo, the Piazza della Signoria, the Uffizi Gallery, the Ponte Vecchio over the Arno River, and Michelangelo's statue of David. Overnight in Florence.

Meals:  B

After breakfast the trip concludes.

Meals:  B



The map and elevation chart are for illustrative purposes only and meant to provide general guidelines.
On self guided trips, actual route information provided before departure will be more detailed.


  • 6 breakfasts - varied buffet breakfasts are served at each hotel
  • 6 nights in 3-4 star hotels on a twinshare basis with private facilities. Hotel taxes extra, payable locally - allow €15-20)
  • 27 speed touring bike rental with puncture resistant tyres, pannier, helmet and gel saddle (e-bikes available - supplement applies)
  • Luggage transfers - 1 bag per person weighing a max of 20kgs.
  • Digital information pack including route notes, maps, navigational App (can be used offline), GPS Tracks and travel guide per room booked
  • Emergency hotline

  • Travel to and from Pisa and Florence
  • Lunches, dinners and drinks
  • Local hotel taxes (payabale locally directly to the hotel)
  • Entrance fees
  • Tour guide - this is a self guided tour
  • Items of a personal nature
  • Travel insurance

Bike information


moderate to challenging  

MODERATE – GRADE 4 This trip involves 5 days cycling with daily cycles of 25 - 70km/15.5 to 44mi. On average you cycle 45km a day over a hilly landscape with some steeper sections. Though the daily distance is not great, the route can be strenuous at times. Much of the cycle is on asphalt roads with low traffic. There are some sections on dirt paths - about 30%. You will need a good level of fitness to participate fully in this adventure. You need only carry your personal items including a water bottle. Your luggage is transported for you between hotels.

Departure dates

Every Saturday from 30 Mar to 12 Oct


Mid Season
High Season
High season is from 11 May to 6 September, mid season is from 20 Apr to 10 May and 7 to 27 Sep, supplement applies
Due to logistics this trip is not suitable for solo travellers. It is possible for single travellers to book on a date which already has travellers. Contact our team for more details.
Other departure dates available for groups of 6 or more.

Want to organise a private group?

Fundraising events, sporting groups, family treats; learn how you can organise a Private Group from just 6 travellers.

Priceper person from


Options & Supplements*
  • E Bike SupplementUSD$160
  • Single SupplementUSD$350
*Prices listed are per person

Trip reviews

Why travel with us

Making Europe Affordable

We offer different levels of accommodation and comfort so that even the most budget conscious can treat themselves to active holidays on Europe's most celebrated tracks and trails. Our trips are great value for money because you only pay for what you want.  

Self-Guided Specialists

Our wide range of self-guided itineraries embody the UTracks philosophy of exploring Europe your way. We handle the logistics so all that's left for you to do is enjoy exploring Europe at your own pace. Most depart daily with a minimum of two people, meaning maximum flexibility.

Our Wide Range

With close to 400 trips in almost 50 countries, including the largest range of bike & boat holidays in Europe, we're confident that we can organise an Alps walk, Camino de Santiago or Via Francigena experience, Food Lovers' trip or a tour in a lesser-known pocket of Europe that you will love. 

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