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Tuscany Pisa, Siena and Florence 7-days Cycling Tour (Level 3)

  • 6days
  • Italy

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Cycling Tours Europe
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Grand Tour 7 Day Self-Guided Cycling

Explore the enchanting region of Tuscany, with its landscapes that resemble paintings and hills that are perfect for cycling. Warm up your legs and enter medieval villages such as Gaiole in Chianti, San Gimignano, Monteriggioni, which invite you to gourmet breaks and appreciate the art that surrounds you. Every corner of Tuscany is a treasure waiting to be discovered, making it a true Grand Tour. Your journey begins and ends in two well-known cities: Pisa and Florence! 

Highlights:

  • The historic villages that unfold one after the other
  • Pedaling up and down the hills of Chianti and Val d'Elsa, among vineyards and olives
  • Florence, which welcomes you in all its Renaissance splendor 

Tour Character: Level 3

  • Total length: 235 km
  • Terrain: 95% tarmac, 5% unpaved
  • Train connection among the overnight stays: none
  • Possibility to shorten the itinerary by taking the train: day 2

This biking week is specifically designed for regular cyclists who are in good physical shape. The daily stages are not too long, about 45 km, but they cover hilly landscapes with numerous climbs and descents, including some steep inclines. This route is recommended only for those who are well-trained. 

Included in the Cycling Tour:

  • 6-nights in 3* and 4* hotel accommodation
  • 6 Breakfast
  • App including maps, roadbook, points of interest and GPS tracks
  • Digital information
  • Luggage transportation (1 piece, 20kg per person)
  • 7-day Hotline service

Not included in the Tour:

  • Local taxes (approx 10-20 EUR)
  • Train transfers
  • Tips
  • Bike rental
  • Bike helmet - 15 EUR
  • Anything not mentioned in 'included' 

Notes: 

  • Departures Saturdays - Special departures for groups 6+
  • 730 EUR for third person in triple room
  • Extra nights in Pisa: From 75 EUR (double) or 135 EUR (single)
  • Extra nights on request in Florence

Arrival/Departure:

  • Pisa is connected with the following airports: Pisa: about 5km, Florence: about 90km

If you would like to rent a bike (110 EUR) or E-bike (270 EUR), please contact our office when booking: [email protected] 

Slow Tours offers a number of other Cycling Tours in Europe

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  • Day 1

    Pisa

    Individual arrival and overnight. The city is famous all over the world for its magic Piazza dei Miracoli with the characteristic leaning tower, the bell tower of the city cathedral. Part of the UNESCO World Heritage list since 1987, besides a large number of monuments it also offers the friendly and lively atmosphere of a university city.

  • Day 2

    Pisa - Casciana Terme (45 km)

    Along the river Arno you will reach Pontedera, a rather modernized district, home to the wine company Castellani, and a sweets factory called Amedei. Your ride will take you through olive groves and vineyards, perfect for an immersion in nature. 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.

  • Day 3

    Casciana Terme - San Gimignano/Colle Val d’Elsa (50/70 km)

    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!

  • Day 4

    San Gimignano/Colle Val d’Elsa - Siena (45/25 km)

    By taking the olden paths of the 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, superb medieval town, is just ahead, easily distinguish it by old brick buildings and the crown of Torre del Mangia.

  • Day 5

    Siena - Greve in Chianti (55 km)

    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.

  • Day 6

    Greve in Chianti - Florence (35 km)

    Your last cycle day will bring you to a small town called Mercatale, where you will be given wine-tasting opportunities from its local wine cellars. After ten kilometres trot off to Impruneta, a neighbouring district filled with terracotta art. Back on your saddle, Florence is waiting for you! Tuscany's capital is known for its wealth in culture, architecture and art. This bustling metropolis is considered the birthplace of the Renaissance and you can immediately see hints of artisan decor embellished upon buildings and squares.

  • Day 7

    Florence

    Departure after breakfast.

    Due to organisational reasons, weather conditions or provisions issued by local authorities, the itinerary may be subject to some changes before and/or during your holiday. For example, along the way you may find temporary deviations caused by roadworks, which cannot be foreseen

  • Day 8

    in this case please follow the indications you will find on site.

  • Read More

Tours marked with are special prices.

Start End Max. No. Guests Accommodation Price p.p.
Mar 29 2025 Apr 04 2025 10 Single rooms 1,230€
Double rooms 890€
Apr 05 2025 Apr 11 2025 10 Single rooms 1,230€
Double rooms 890€
Apr 12 2025 Apr 18 2025 10 Single rooms 1,230€
Double rooms 890€
Apr 19 2025 Apr 25 2025 10 Single rooms 1,390€
Double rooms 1,050€
Apr 26 2025 May 02 2025 10 Single rooms 1,390€
Double rooms 1,050€
May 03 2025 May 09 2025 10 Single rooms 1,390€
Double rooms 1,050€
May 10 2025 May 16 2025 10 Single rooms 1,440€
Double rooms 1,100€
May 17 2025 May 23 2025 10 Single rooms 1,440€
Double rooms 1,100€
May 24 2025 May 30 2025 10 Single rooms 1,440€
Double rooms 1,100€
May 31 2025 Jun 06 2025 10 Single rooms 1,440€
Double rooms 1,100€
Jun 07 2025 Jun 13 2025 10 Single rooms 1,440€
Double rooms 1,100€
Jun 14 2025 Jun 20 2025 10 Single rooms 1,440€
Double rooms 1,100€
Jun 21 2025 Jun 27 2025 10 Single rooms 1,440€
Double rooms 1,100€
Jun 28 2025 Jul 04 2025 10 Single rooms 1,440€
Double rooms 1,100€
Jul 05 2025 Jul 11 2025 10 Single rooms 1,440€
Double rooms 1,100€
Jul 12 2025 Jul 18 2025 10 Single rooms 1,440€
Double rooms 1,100€
Jul 19 2025 Jul 25 2025 10 Single rooms 1,440€
Double rooms 1,100€
Jul 26 2025 Aug 01 2025 10 Single rooms 1,440€
Double rooms 1,100€
Aug 02 2025 Aug 08 2025 10 Single rooms 1,440€
Double rooms 1,100€
Aug 09 2025 Aug 15 2025 10 Single rooms 1,440€
Double rooms 1,100€
Aug 16 2025 Aug 22 2025 10 Single rooms 1,440€
Double rooms 1,100€
Aug 23 2025 Aug 29 2025 10 Single rooms 1,440€
Double rooms 1,100€
Aug 30 2025 Sep 05 2025 10 Single rooms 1,440€
Double rooms 1,100€
Sep 06 2025 Sep 12 2025 10 Single rooms 1,390€
Double rooms 1,050€
Sep 13 2025 Sep 19 2025 10 Single rooms 1,390€
Double rooms 1,050€
Sep 20 2025 Sep 26 2025 10 Single rooms 1,390€
Double rooms 1,050€
Sep 27 2025 Oct 03 2025 10 Single rooms 1,230€
Double rooms 890€
Oct 04 2025 Oct 10 2025 10 Single rooms 1,230€
Double rooms 890€
Oct 11 2025 Oct 17 2025 10 Single rooms 1,230€
Double rooms 890€

Car rental in Italy

If you would like to drive yourself before or after your tour, ask us for a quote on any brand new Renault, Peugeot or Citroen vehicle for driving in Europe.

Pick up your vehicle from most capital cities in Europe and return it to your drop off destination. Top insurance cover. Email [email protected] for a competitive quote

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