Chianti to San Gimignano Bike Tour

Our Tuscany vespa tour takes us on a breathtaking drive through the hills of Chianti passing vineyards, villas and olive groves.

Chianti to San Gimignano Bike Tour

From the most famous wine area in Tuscany to the fantastic hilltop town known as the “Manhattan of the middle ages”.

You will ride between vineyards and olive groves with beautiful views of the rolling Tuscan hills. Plenty of breathtaking photo stops will allow you to take in the incredible historic villages. When you think it’s all over, the best part is still to come: a 1.5 hour stroll in the famous 14 towered town - a UNESCO world heritage site (San Gimignano). At the end of the tour a wine tasting will complete the best day of your vacation in Italy.


Mixed terrain (paved roads and gravel roads)


7.5 hours


26km (16miles)

Total Elevation:

400m (1300ft)

Skill level:

Intermediate/ Advance

Number of participants:


Support vehicle:


 Departure / Meeting Point

Our Chianti to San Gimignano bike tour departs from Florence at 9:30am. Our office is located on Via Ghibellina 34red 50122, 3 minutes walking distance from Santa Croce. We are located opposite a sushi ristorante. Look out for the ACTIVE TOURS ITALY sign. Please be at the meeting point 30 minutes prior to departure. click here for a map.

Directions from Piazza del Duomo (The dome church) Head east on Piazza del Duomo toward Via del Campanile, Turn right at Via del Proconsolo, Turn left at Via Ghibellina. Our office will be on your left.

  Tours Requirements

In order to ride with us you must be able to tick ALL the following.

 I can ride a bike confidently.

 I am physically fit and healthy.

 I am competent on main roads.

  Cancellation Policy

 A cancellation received more than 72 hours (3 days) prior to a clients scheduled tour date will not incur any fee.

 A cancellation received within 72 hours of a clients scheduled tour date or a no-show will incur full cost of the tour booked.

View full terms and conditions


 Fully guided semi-private tour

 Van transfers to/from the tour starting point in the Chianti region

 High quality 27-speeds hybrid bikes

 Helmets and water bottles

 English speaking tour guides

 Chianti wine and olive oil tasting

  Not Included




145,00 per person

(All sales tax included). Prices valid until further notice.


  Depart from Florence at 9:30am (meeting time 9:00am).

  Transfer by van to Castello di Poppiano.

  Gear up to bike on the Tuscan rolling hills: bike orientation and safety briefing.

  Enjoy winding roads, ancient villages and “strade bianche” (Tuscany's famous white roads).

  Keep riding among vineyards and olive groves with frequent stops for pictures and to take in the spectacular views of the Tuscan countryside.

  At the end of the scenic ride the tour continues by van to San Gimignano.

  You’ll have 1.5 hours to freely enjoy the town and have lunch (not included in the price).

  After, there will be a transfer back to Castello di Poppiano for a wine and extra virgin olive oil tasting (Laudemio extra virgin olive oil).

  Transfer back to Florence for a 5:30pm drop off.

We welcome non cyclists on our tour.
Contact us for more details.

Meeting Point

If you want to meet us at our starting point (in the countryside) rather then in Florence, please email us or leave a note in the comments section when you booked and we will forward on details of time and directions.

To meet us at our starting point
(in the countryside) click here for more details.

Discover the tours

Tuscany vespa tours offers one day vespa tours just south of Florence in the heart of the Chianti wine region. Our single day vespa tour in Tuscany has everything from wine and oil tasting, to visiting a charming 12th century medieval castle which is home to a Count and Countess.