+44 (0)1506 635399 info@hookedoncycling.co.uk
+44 (0)1506 635399 info@hookedoncycling.co.uk

Tuscany Chianti Cycle Tour

Booking Form
Enquiry Form
Full Name*
Email Address*
Your Enquiry*
* I agree with Terms of Service and Privacy Statement.
Please agree to all the terms and conditions before proceeding to the next step

Please click the link below to book this tour

Proceed Booking

Proceed Booking

Save To Wish List

Adding item to wishlist requires an account

Homepage > Italy > Tuscany Chianti Cycle Tour
  • Duration: 7 Nights
  • Difficulty: Level 2 (Some days 2-3)
  • Tour Type: Self Guided
  • Availability: Saturdays from 23rd March to 12th October
  • Location: Montecatini Terme

Tuscany Chianti

Tour Details

On this bike vacation often by surprise a wonderful castle or a stylish villa emerges from behind the cypress trees. Surrounded by silvery-green olive groves and the violet of the lilies. Tuscany has always been a magic place for people all around the world. Tuscany has a dreamlike but also hilly landscape. Experience cities that truly delight with histories such as Siena, Florence and Pisa, be amazed at the towers of San Gimignano. We cycle on lovely side paths and country lanes from one famous city to another. A true delight!

Starting Location

Montecatini Terme

Price Includes

  • 7 nights Bed and Breakfast
  • 3 star hotels
  • Information Pack
  • Luggage transfers
  • GPS Files on request
  • Bus transfer Greve to Florence
  • Smart Phone App for Navigation

Price Excludes

  • Transport before and after tour
  • Flights
  • Travel Insurance
  • Hybrid Rental Bike with bike rental insurance
  • E-Bike Rental Bike with bike rental insurance
  • City Tax
  • Extra nights in Florence
  • Upgraded hotels to 3/4 star hotels – some have pools
  • Public transport
Trip Info

Accommodation – Subject to Change

Montecatini Terme                   – Hotel Manzoni, Upgrade Grand Hotel Croce di Malta

Pisa                                         – Hotel Soggiorno, Upgrade Hotel Repubblica Marinara

Casciana Terme                      – Albergo Stella, Upgrade Albergo Roma

San Gimignano                        – Albergo Le Colline, Upgrade Hotel San Michelle

Siena                                       – Hotel Italia

Florence                                  – Hotel Grifone, Upgrade Grand Hotel Adriatico

Route Characteristics

You will cycle along quiet minor roads and even sometimes on country roads. Closer to the bigger cities there will be more traffic, which is unavoidable.

Travel Insurance

It is a requirement of booking this tour with Hooked on Cycling that you have suitable travel insurance which covers you for the chosen activity and for emergency evacuation and hospital care.


Day 1Saturday Individual arrival at Montecatini Terme

Tour information provided and bikes are handed over on arrival at your pre-tour meeting late afternoon. Take time to explore this spa town, maybe sample the healing waters or relaxing massage. Montecatini has many restaurants to choose from.

Day 2Sunday Vinci  35 miles 55 km

Cycling on small paths through olive groves of Montecatini Terme through the vast plains of the valley of Valdenievole to Vinci which is the birthplace of Leonardo. You can visit the Vinci museum’s which has a collection of many of his machines he invented, you can also visit his house where he was born before making your way back to Montecatini Terme.

Day 3Monday Pisa 25-56 miles 40-90 km

Today you have an option, to cycle passing the small medieval town of Monte Carlo which is famous for its wines on your way towards Lucca or alternatively by train to Lucca.  Once in Lucca, you can then take a city tour by cycling along the city walls which are 5km long and you can cycle all around the top of them. Then it is on to the lake of Massacciuccoli also known as lake of Giacomo Puccini and on to Pisa, where you can visit the famous landmarks, Miracle square with its leaning tower, cathedral and baptistery. Climb the leaning tower and visit the cathedral.

Day 4Tuesday Casciana Terme 31 miles 50 km

Cycling from Pisa along the river Arno and then on cycle paths and lanes to the idyllic spring town Casciana Terme. Today’s route is generally flat with some small climbs. You shall pass many fertile fields growing such items as peaches, grapes producing sweet wines and of course olives.

Day 5Wednesday San Gimignano/Poggibonsi 35 miles 55 km

Cycling through vineyards and soft hills to San Gimignano. Now you are inland from the coast the landscape is more undulating, you will cycle through many little historic villages some as though time has stood still. Eventually arriving in San Gimignano sitting on top of the hill. This ancient fortified town is beautifully restored and you can spend many hours looking around walking through the cobbled streets. Of course, it is often better in the evening when the daytime tourists have gone home.

Day 6 Thursday Siena 31 miles 50 km

Through Tuscany’s wonderful landscape to the architectonic paradise Siena. The quiet roads will lead you through the rolling countryside to this fabulous city. Many chances on your route to stop at the local bar and take a coffee and watch the time go by. This is one of Italy’s most wonderful Roman cities. The old town is a must to explore, see the large square and town hall, notice it is the only building with a clock. This is because in ancient times the city leader had control over time and therefore the residents of the city. Twice per year, a famous horse race takes place in this old square, 10 horses and 20 thousand spectators crammed in the centre.

Day 7Friday Florence 30 miles 50 km + transfer into Florence

Today leaving Siena you cycle through the hilly Chianti region, where the “Chianti Classico” wines come from. You are heading for Greve in Chianti with its lovely town square and wine sample museums. From there you drop off your rental bikes and take a bus transfer into Florence. This bus eliminates a busy section of the roads into Florence. Now you have time to explore this very art city with this great Basilica and little streets. If you have your own bikes these are transferred into Florence.

Day 8Saturday Departure

Individual departure or extension of your stay.

If you hunting for a tour where you can sample glorious wines then we have several to choose from, also consider our Tasty Piemonte tour with its famous Barolo wines and the Rose wines Wine Trails of Provence .


How to get there

By Plane Fly to Pisa with Ryanair, Jet2 or British airways. From Pisa it is around 1 hour by train, from Florence back to Pisa is also around a 1 hour train journey so access to the tour is very easy.

Book Now

2024 Prices – For a complete tour price breakdown please click the book now button and select your holiday tour date. Prices will then be listed.

 Tour Code Prices From (per person) Book Now
Tus2U7 (7 Nights) from £1115 Book Now
Tus2U7 – Upgrade (7 Nights) from £1267 Book Now
Tour Images
Tuscany landscape
YouTube video