Bike tour, Tuscany, Italy (guided groups)

6 days

•

From Florence to Montepulciano

5.0

4 traveler reviews

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From

US $2,900 per person

Price based on Cheapest Room

Price based on Shared Room

Price based on Private Single Room

Price based on Private Double Room

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1 Adult2 Adults, 1 Child2 Children

Best price guarantee Learn More

Plan your adventure:

Gold Operator: The Chain Gang Cycle Tours
Bicycle: Pedal-powered journeys for two-wheeled explorers
Group Tour: Join a group and forge lifelong friendships
Partially Guided: Independent travel, featuring selected guided excursions
Medium Intensity: Travelers should be comfortable with somewhat-demanding activities
Guided in English: Other languages on request: Italian, French
Group Size 4 - 15
Ages 12+

Image of a map showing the route of the tour

Itinerary

Day 1
Florence to San Gimignano
Meals
Dinner (Dinner with local Vernaccia di San Gimignano wine, with views across Chianti)
Landmarks
San Gimignano
Day 2
San Gimignano - Chianti
Meals
Breakfast, Dinner
Included Activities
- Cycling through vineyards and cypress tree avenues in Chianti
Optional Activities
- Explore San Gimignano
Landmarks
San Gimignano
Chianti
Barberino
Day 3
Chianti - Vagliagli
Meals
Breakfast, Dinner
Included Activities
- Visit cantine in Greve-in-Chianti
- Wine tasting at Chianti Classico producers
Optional Activities
- Explore Greve-in-Chianti
- Explore Radda-in-Chianti
Landmarks
Greve-in-Chianti
Radda-in-Chianti
Chianti Classico
Day 4
Chianti - Siena
Meals
Breakfast, Dinner
Included Activities
- Cycling through Siena
Optional Activities
- Visit Monteriggioni
Landmarks
Monteriggioni
Siena
Piazza del Campo
Day 5
Siena to Asciano
Meals
Breakfast, Dinner
Included Activities
- Cycling through le Crete countryside
Landmarks
le Crete
Asciano
Day 6
Asciano - Montalcino
Meals
Breakfast, Dinner
Included Activities
- Visit Abbey of Monte Oliveto Maggiore
- Wine tasting at Val di Suga estate
- Cycling through Tuscan countryside
Optional Activities
- View frescoes of St Benedict at Abbey of Monte Oliveto Maggiore
Landmarks
Abbey of Monte Oliveto Maggiore
Montalcino
Day 7
Montalcino - Montepulciano
Meals
Breakfast, Dinner
Included Activities
- Visit Abbey at Saint Antimo
- Wine tasting at Avignonesi estate
- Cycling through Tuscan countryside
Optional Activities
- Explore Pienza
Landmarks
Abbey at Saint Antimo
Pienza
Montepulciano
Day 8
Montepulciano to Florence - Pisa - Bologna
Meals
Breakfast

Landmarks
San Gimignano

Landmarks
San Gimignano
Chianti
Barberino

Landmarks
Greve-in-Chianti
Radda-in-Chianti
Chianti Classico

Landmarks
Monteriggioni
Siena
Piazza del Campo

Landmarks
le Crete
Asciano

Landmarks
Abbey of Monte Oliveto Maggiore
Montalcino

Landmarks
Abbey at Saint Antimo
Pienza
Montepulciano

What's Included

Expand All

Accommodation
Guide
Meals
Additional Services
Optional Extras

What's Not Included

Additional Services

Operated by

The Chain Gang Cycle Tours

Gold Operator

Rating: 4.9(39 reviews)
Response time: within 3 days
Response rate: 100%
Cancellation policy

Traveler Reviews

5.0

Overall rating based on 4 Reviews

Transport
5.0
Guide
5.0
Accommodation
4.8
Food
5.0
Tour Operator
4.9

P
Paul
February 17th, 2018
Chain Gang focus on small group cycling holidays that take in stunning scenery (photo op delight!) and great local...
Chain Gang focus on small group cycling holidays that take in stunning scenery (photo op delight!) and great local food and wine. Knowledgeable guides take you off the beaten track to some delightful towns and villages where you can sample great food or patter around to your hearts content. The accommodation along the way is beautiful, and not the sort of thing you could easily find yourself. Luggage is all taken care of and you just need to cycle to your nights accommodation. Bikes, helmets, jackets etc... are all supplied - just bring yourself. All in all, some of the best cycle tours we've done are with this group - no wonder so many people keep coming back. Highly recommended!Show more
Traveled in September 2017
P
Paul
February 1st, 2018
In September 2017, our group of 4 cyclists did the Umbria bicycle tour with Chain Gang tours. There were other riders...
In September 2017, our group of 4 cyclists did the Umbria bicycle tour with Chain Gang tours. There were other riders on the tour as well so we were 9 riders in total. We met in Orvieto and were transported to the small tour where the tour began. As we cycled through small towns and pleasant countryside, it became clear our guide was very knowledgeable about the history of the country. We were seeing beautiful country but also leaning about its past as we travelled through it. The hotels and meals were first rate. The guide and his assistant (van driver) made sure our bikes were in good working order each day. We saw beautiful countryside, had great meals and enjoyed great company. What could be better than that. Show more
Traveled in September 2017
M
Mike
January 25th, 2018
Had a fabulous week cycling through beautiful countryside in Tuscany with The Chain Gang. CG owner Bernard was our...
Show more
Traveled in September 2017
D
David
January 25th, 2018
I have now completed two tours with The Chain Gang and both were excellent, with fine cuisine, very nice company and...
I have now completed two tours with The Chain Gang and both were excellent, with fine cuisine, very nice company and very supportive and informed guides. Our trip through Alsace, France was very picturesque, visiting many ancient towns and inns along the way. Our Tuscany trip was very exciting biking through challenging and hilly terrain, on both paved and dirt roads. Our guide Bernard was warm, supportive and very accommodating as my wife navigated the Tuscany hills on a tandem. Bernard is fun, very well informed and speaks Italian, so he was also helpful at meal time with the wait staff working out our meal orders. I highly recommend Chain Gang if you want a pleasant and moderate cycling experience through some of the most picturesque countrysides in Europe. Show more
Traveled in September 2017

Dates & Availability

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1 Adult2 Adults, 1 Child2 Children

Upcoming departures

Instant Confirmation
From Saturday
5 Sep, 2026
To Thursday
10 Sep, 2026
English, Italian
This departure date is available and will 100% depart
Guaranteed departure
From:
US $2,900 per person
Multiple Room Types
Instant Confirmation
From Saturday
19 Sep, 2026
To Thursday
24 Sep, 2026
English, Italian, French +2 more
From:
US $2,900 per person
Multiple Room Types

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Can’t find the answer to your question?

From

US $2,900 per person

Price based on Cheapest Room

Price based on Shared Room

Price based on Private Single Room

Price based on Private Double Room

Select Date

1 Adult2 Adults, 1 Child2 Children

Best price guarantee Learn More

Plan your adventure:

Good to Know

Tour ID: 99288

Currency
€
Euro
Italy
Plugs & Adapters
As a traveler from USA, Canada, England, Australia, New Zealand, South Africa you will need an adaptor for type L.
Type L
Italy
Visa
- Unfortunately we cannot offer you a visa application service. Whether you need a visa or not depends on your nationality and where you wish to travel. Assuming your home country does not have a visa agreement with the country you're planning to visit, you will need to apply for a visa in advance of your scheduled departure.
- Here is an indication for which countries you might need a visa. Please contact the local embassy for help applying for visas to these places.
Payment information
- For any tour departing before May 30th, 2026 a full payment is necessary. For tours departing after May 30th, 2026, a minimum payment of 10% is required to confirm your booking with The Chain Gang Cycle Tours. The final payment will be automatically charged to your credit card on the designated due date. The final payment of the remaining balance is required at least 30 days prior to the departure date of your tour. TourRadar never charges you a booking fee and will charge you in the stated currency.
- Some departure dates and prices may vary and The Chain Gang Cycle Tours will contact you with any discrepancies before your booking is confirmed.
- The following cards are accepted for "The Chain Gang Cycle Tours" tours: Visa, Maestro, Mastercard, American Express or PayPal. TourRadar does NOT charge you an extra fee for using any of these payment methods.
Cancellation Policy
- Your money is safe with TourRadar, as we only pay the tour operator after your tour has departed.
- TourRadar is an authorized Agent of The Chain Gang Cycle Tours. Please familiarize yourself with the The Chain Gang Cycle Tours payment, cancellation and refund conditions.
Accessibility
Some tours are not suitable for mobility-restricted traveler, however, some operators may be able to accommodate special requests. For any enquiries, you can contact our customer support team, who are ready and waiting to help you.
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Bike tour in Tuscany, Italy.

Bike tour, Tuscany, Italy (guided groups)

Itinerary

Florence to San Gimignano

San Gimignano - Chianti

Included Activities

Optional Activities

Chianti - Vagliagli

Included Activities

Optional Activities

Chianti - Siena

Included Activities

Optional Activities

Siena to Asciano

Included Activities

Asciano - Montalcino

Included Activities

Optional Activities

Montalcino - Montepulciano

Included Activities

Optional Activities

Montepulciano to Florence - Pisa - Bologna

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What's Included

What's Not Included

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Bike tour, Tuscany, Italy (guided groups)

Itinerary

Included Activities

Optional Activities

Included Activities

Optional Activities

Included Activities

Optional Activities

Included Activities

Included Activities

Optional Activities

Included Activities

Optional Activities

Want to read it later?

What's Included

What's Not Included

Traveler Reviews

Dates & Availability

Want to read it later?

Why book with TourRadar?

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Good to Know

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