From

NZ $2,969 per person

Postcard Southern Tuscany - Cycling Cortona, Montalcino, Siena - Classic Self Guided

8 days

•

From Cortona to Siena

5.0

2 traveler reviews

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We loved everything about our self-guided tour. The itinerary kept us on less-traveled roads as much as possible.
K
kathysteinberger, traveled in January
5.0
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From

NZ $2,969 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

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Plan your adventure:

Operator: BikesPlus Travel
Bicycle: Pedal-powered journeys for two-wheeled explorers
Private Tour: Travel exclusively with your friends and family
Self-guided: Independent exploration, backed by expert advice and support
High Intensity: Travelers should be in very good physical condition and expect continuous demanding activities
Guided in English
All Ages Welcome

Image of a map showing the route of the tour

Highlights

Discover the heart of the “Under the Tuscan sun” book
Pedal through the beautiful UNESCO Val D’Orcia
Take time to relax tasting a good glass of wine
Try the homemade pasta and sublime local cheese
Immerse in the countryside’s postcard landscapes

Itinerary

View Full Itinerary

Introduction

Day 1 Arrive today in Cortona
Day 2 Loop ride to Trasimeno Lake and surrounding hills
Day 3 Bicycle to Montepulciano and Pienza
Day 4 Loop ride in the Orcia Valley
Day 5 Bicycle to the wine town of Montalcino
Day 6 Loop ride to Bagno Vignoni and the Abbey of Sant Antimo
Day 7 Bicycle to Siena
Day 8 Tour ends in Siena

What's Included

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Accommodation
Meals
Additional Services
Free eSIM
TourRadar offers the lead traveler (the person who booked) a free 1GB eSIM for the trip. The eSIM is redeemable only through the TourRadar app 72 hours before departure.
Optional Extras

What's Not Included

Flights
Insurance
Additional Services

Operated by

BikesPlus Travel

4.7

(46 reviews)

Number of tours

Age Range

3 to 90 years old

Response time

within 2 days

Response rate

100%

BikesPlus Travel has been running bicycle tours in Europe longer than most...

Cancellation Policy

A transparent overview of applicable fees.

Travel Insurance

Be covered for any unforseen circumstances.

Customer Reviews

Overall Rating
Excellent
5.0
Itinerary
Excellent
5.0
Guide
Excellent
5.0
Transport
Excellent
5.0
Accommodation
Excellent
5.0
Food
Excellent
5.0
Tour Operator
BikesPlus Travel
4.7

Michael
· July 13th, 2019
From beginning to end, Cycle Europe was fantastic. The pre-planning and communication was incredible. The bikes were titanium bikes, with quality components. The sent staff members to expertly fit the bikes, the routes they planned was perfect, and the hotels were fabulous. On top of everything else, they were willing to help us for our entire vacation. They helped set up a cooking class for us in Lucca, helped arrange a special ceremony for our parent's 50th anniversary, and helped arrange our private transfer. They were really amazing.
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Trip date: July 2019
K
kathysteinberger
· January 5th, 2019
Although the route was very hilly, we loved everything about our self-guided tour. The itinerary kept us on less-traveled roads as much as possible, and took us through small scenic towns with gorgeous views. We also appreciated the opportunity to tour several monasteries and scenic spots along the way. Our accommodations were very good and we had a hearty, tasty breakfast every morning. The combination of paper maps with precise directions and GPS ensured that we were hardly ever lost. We were also impressed with the quality of the bikes and the expert fitting and orientation we received before we set out. I'd highly recommend this tour for bikers who don't mind lots of elevation change!
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Trip date: July 2018

Dates & Availability

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1 Adult2 Adults, 1 Child2 Children

Upcoming departures

Hurry, deals only available for a limited time!

Ends on 12 Nov, 2025

From Monday
2 Mar, 2026
To Monday
9 Mar, 2026
English
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Departure on request
From:
NZ $2,969 per person
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From Monday
9 Mar, 2026
To Monday
16 Mar, 2026
English
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From:
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From Monday
16 Mar, 2026
To Monday
23 Mar, 2026
English
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From Monday
23 Mar, 2026
To Monday
30 Mar, 2026
English
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From:
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From Monday
30 Mar, 2026
To Monday
6 Apr, 2026
English
Check the availability with the operator
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From:
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From Monday
6 Apr, 2026
To Monday
13 Apr, 2026
English
Check the availability with the operator
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From Monday
13 Apr, 2026
To Monday
20 Apr, 2026
English
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From:
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From Monday
20 Apr, 2026
To Monday
27 Apr, 2026
English
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From:
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From Monday
27 Apr, 2026
To Monday
4 May, 2026
English
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From:
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From Monday
4 May, 2026
To Monday
11 May, 2026
English
Check the availability with the operator
Departure on request
From:
NZ $3,170 per person
Multiple Room Types

Why book with TourRadar?

Trusted and vetted operators
Rated excellent on
Best price guarantee

24/7 customer support
Earn $50 in travel credits
Free eSim with every purchase

To protect your payment and ensure your booking will be processed in Australia, never transfer or communicate outside of the TourRadar website or app.

More benefits

Can’t find the answer to your question?

Reach out to the experts at BikesPlus Travel with your enquiry, they usually respond within 2 days.

From

NZ $2,969 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: 109997

Currency
€
Euro
Italy
Plugs & Adapters
As a traveler from New Zealand 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 January 29th, 2026 a full payment is necessary. For tours departing after January 29th, 2026, a minimum payment of $700 is required to confirm your booking with BikesPlus Travel. 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 90 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 BikesPlus Travel will contact you with any discrepancies before your booking is confirmed.
- The following cards are accepted for "BikesPlus Travel" 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 BikesPlus Travel. Please familiarize yourself with the BikesPlus Travel 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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