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Tuscany with Charm Self-guided 8-day Cycling Tour (Level 4)

  • 8days
  • Italy

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Cycling Tours Europe
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8-day Cycling Tour Tuscany with Charm

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.

Highlights:

  • The museum of the genius Leonardo da Vinci
  • Cycling across the Piazza dei Miracoli in Pisa
  • The Chianti wine region
  • The breathtaking Tuscan hills

Tour character: Level 4

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.

Included in the Cycling Tour:

  • 7 nights accommodation in 4* hotels with charm
  • Breakfast
  • Welcome briefing 
  • Luggage transfer between the hotels
  • Digital travel documents incl. navigation app, GPS-data, route book
  • 7-day service hotline

Not included in the Tour:

  • Bike rental, including rental bike insurance
  • Tourist tax, if due
  • Printed route book, per person EUR 20
  • Anything not mentioned in 'included'

If you would like to rent a bike (109 EUR) or E-bike (299 EUR) please email: [email protected]

Travel Insurance:

  • Wander the World Without Worry! For your global travel insurance and evacuation services click on this link to get a quote (all quotes are in USD) in just a few moments: Global Travel Insurance

Notes:

  • Departures Saturdays
  • Extra nights
    • Montecatini Terme: From 129 EUR p.p (+65 EUR single person)
    • Florence: From 165 EUR p.p (+125 EUR single person)
  • Rental bike PLUS - 189 EUR on request
  • On ‘Cycle Tours with Charm’ you can enjoy the full service of 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.

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
  • Return transfer to Montecatini Terme every SAT, costs EUR 69 per person, EUR 49 for your own bike, reservation is necessary, to be paid for in advance

Slow Tours offers a number of other Cycling Tours in Europe

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  • Day 1

    Arrival in Montecatini Terme

    Montecatini Terme is an elegant spa town in the heart of Tuscany. Discover graceful parks, historic architecture and a relaxing atmosphere. A special highlight is riding the historic funicular to Montecatini Alto with beautiful views across the surrounding Tuscan countryside.

  • Day 2

    Montecatini Terme – Pisa approx. 40-90 km

    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.

  • Day 3

    Pisa – Casciana Terme approx. 50 km

    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

  • Day 4

    Casciana Terme – San Gimignano approx. 55 km

    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.

  • Day 5

    San Gimignano – Siena approx. 50 km

    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.

  • Day 6

    Siena – Castellina in Chianti approx. 40 km

    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.

  • Day 7

    Castellina in Chianti - Florenz approx. 65 km

    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.

  • Day 8

    Departure or Extension

  • Read More

Tours marked with are special prices.

Start End Max. No. Guests Accommodation Price p.p.
Oct 10 2026 Oct 17 2026 10 Single rooms 2,158€
Double rooms 1,579€
Mar 27 2027 Apr 03 2027 10 Single rooms 2,258€
Double rooms 1,649€
Apr 03 2027 Apr 10 2027 10 Single rooms 2,258€
Double rooms 1,649€
Apr 10 2027 Apr 17 2027 10 Single rooms 2,258€
Double rooms 1,649€
Apr 17 2027 Apr 24 2027 10 Single rooms 2,338€
Double rooms 1,729€
Apr 24 2027 May 01 2027 10 Single rooms 2,338€
Double rooms 1,729€
May 01 2027 May 08 2027 10 Single rooms 2,338€
Double rooms 1,729€
May 08 2027 May 15 2027 10 Single rooms 2,338€
Double rooms 1,729€
May 15 2027 May 22 2027 10 Single rooms 2,408€
Double rooms 1,799€
May 22 2027 May 29 2027 10 Single rooms 2,408€
Double rooms 1,799€
May 29 2027 Jun 05 2027 10 Single rooms 2,408€
Double rooms 1,799€
Jun 05 2027 Jun 12 2027 10 Single rooms 2,408€
Double rooms 1,799€
Jun 12 2027 Jun 19 2027 10 Single rooms 2,408€
Double rooms 1,799€
Jun 19 2027 Jun 26 2027 10 Single rooms 2,408€
Double rooms 1,799€
Jun 26 2027 Jul 03 2027 10 Single rooms 2,408€
Double rooms 1,799€
Jul 03 2027 Jul 10 2027 10 Single rooms 2,408€
Double rooms 1,799€
Jul 10 2027 Jul 17 2027 10 Single rooms 2,408€
Double rooms 1,799€
Jul 17 2027 Jul 24 2027 10 Single rooms 2,408€
Double rooms 1,799€
Jul 24 2027 Jul 31 2027 10 Single rooms 2,408€
Double rooms 1,799€
Jul 31 2027 Aug 07 2027 10 Single rooms 2,408€
Double rooms 1,799€
Aug 07 2027 Aug 14 2027 10 Single rooms 2,408€
Double rooms 1,799€
Aug 14 2027 Aug 21 2027 10 Single rooms 2,408€
Double rooms 1,799€
Aug 21 2027 Aug 28 2027 10 Single rooms 2,408€
Double rooms 1,799€
Aug 28 2027 Sep 04 2027 10 Single rooms 2,408€
Double rooms 1,799€
Sep 04 2027 Sep 11 2027 10 Single rooms 2,338€
Double rooms 1,729€
Sep 11 2027 Sep 18 2027 10 Single rooms 2,338€
Double rooms 1,729€
Sep 18 2027 Sep 25 2027 10 Single rooms 2,338€
Double rooms 1,729€
Sep 25 2027 Oct 02 2027 10 Single rooms 2,258€
Double rooms 1,649€
Oct 02 2027 Oct 09 2027 10 Single rooms 2,258€
Double rooms 1,649€
Oct 09 2027 Oct 16 2027 10 Single rooms 2,258€
Double rooms 1,649€

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

Travel insurance for Italy

Wander the World Without Worry

Local language barriers. Lost passport. Unexpected medical expenses. Sometimes, our trips don’t go as planned. That’s why Slow Tours Pty Ltd wants you to have the most robust travel advisory and protection for your vacation.

Ask us for a quote [email protected]

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