From

US $1,678 per person

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

8 days

•

From Cortona to Siena

5.0 (2 reviews)

View all
We loved everything about our self-guided tour. The itinerary kept us on less-traveled roads as much as possible.
kathysteinberger•traveled in January5.0
View all

From

US $1,678 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:

Operator: BikesPlus Travel
Bicycle: Pedal through scenic landscapes on two wheels
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

Itinerary

Day 1
Cortona
Cortona
Meals
Breakfast
Included Activities
- Bike fitting and briefing in English by professional staff
- Explore Cortona's Medieval streets
Optional Activities
- Visit Etruscan Museum
- Visit Diocesan Museum with Fra Angelico paintings
Landmarks
Cortona
Etruscan Museum (MAEC)
Diocesan Museum of Cortona
Day 2
Lake Trasimeno
Lake Trasimeno
Meals
Breakfast
Included Activities
- Cycle ride to Lake Trasimeno with route options
Optional Activities
- Boat ride on Lake Trasimeno to Isola Maggiore
Landmarks
Lake Trasimeno
Isola Maggiore
Day 3
Pienza
Pienza
Meals
Breakfast
Included Activities
- Cycle ride through Montepulciano medieval streets
- Cycle ride to Pienza Renaissance town
Optional Activities
- Visit typical wine cellars in Montepulciano
Landmarks
Montepulciano
Pienza
Day 4
Val d'Orcia
Val d'Orcia
Meals
Breakfast
Included Activities
- Loop ride through Val d'Orcia landscape
- Cycle through Monticchiello Medieval village
Optional Activities
- Sample local wines and cheeses in Pienza
Landmarks
Val d'Orcia
Monticchiello
Day 5
Montalcino
Montalcino
Meals
Breakfast
Included Activities
- Cycle ride from Pienza to Montalcino
- Stop in Trequanda village
Landmarks
Trequanda
Montalcino
Day 6
Montalcino
Montalcino
Meals
Breakfast
Included Activities
- Cycle visit to Abbey of Sant Antimo
Optional Activities
- Visit Bagno Vignoni thermal spa village
- Explore San Quirico d'Orcia
Landmarks
Abbey of Sant Antimo
Castiglione d'Orcia
Bagno Vignoni
San Quirico d'Orcia
Day 7
Siena
Siena
Meals
Breakfast
Included Activities
- Cycle ride to Siena
- Pass by Monte Oliveto Maggiore monastery
- Ride through Crete Senesi chalk hills
Landmarks
Monte Oliveto Maggiore
Crete Senesi
Siena
Day 8
Siena
Siena
Meals
Breakfast
Optional Activities
- Explore Siena for additional days
- Optional guided visit of Siena
Landmarks
Siena

Landmarks
Cortona
Etruscan Museum (MAEC)
Diocesan Museum of Cortona

Landmarks
Lake Trasimeno
Isola Maggiore

Landmarks
Montepulciano
Pienza

Landmarks
Val d'Orcia
Monticchiello

Landmarks
Trequanda
Montalcino

Landmarks
Abbey of Sant Antimo
Castiglione d'Orcia
Bagno Vignoni
San Quirico d'Orcia

Landmarks
Monte Oliveto Maggiore
Crete Senesi
Siena

Landmarks
Siena

What's Included

Expand All

Accommodation
Meals
Additional Services
Optional Extras

What's Not Included

Flights
Insurance
Additional Services

Operated by

BikesPlus Travel

Rating: 4.7 (47 reviews)
Response time: within 2 days
Response rate: 60%
Cancellation policy

Traveler Reviews

5.0

Overall rating based on 2 Reviews

Itinerary
5.0
Transport
5.0
Guide
5.0
Accommodation
5.0
Food
5.0
Tour Operator
4.7

Michael5.0•July 2019
From beginning to end, Cycle Europe was fantastic. The pre-planning and communication was incredible. The bikes...
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.Show more
Traveled in July 2019
kathysteinberger5.0•January 2019
Although the route was very hilly, we loved everything about our self-guided tour. The itinerary kept us on...
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!Show more
Traveled in July 2018

Dates & Availability

Select departure month and travellers

Select Date

1 Adult2 Adults, 1 Child2 Children

Upcoming departures

Hurry, deals only available for a limited time!

Ends on 29 Jul, 2026

From Monday
3 Aug, 2026
To Monday
10 Aug, 2026
English
Check the availability with the operator
Departure on request
From:
US $1,678 per person
Multiple Room Types
Sign up and save
From Monday
10 Aug, 2026
To Monday
17 Aug, 2026
English
Check the availability with the operator
Departure on request
From:
US $1,678 per person
Multiple Room Types
Sign up and save
From Monday
17 Aug, 2026
To Monday
24 Aug, 2026
English
Check the availability with the operator
Departure on request
From:
US $1,678 per person
Multiple Room Types
Sign up and save
From Monday
24 Aug, 2026
To Monday
31 Aug, 2026
English
Check the availability with the operator
Departure on request
From:
US $1,678 per person
Multiple Room Types
Sign up and save
From Monday
31 Aug, 2026
To Monday
7 Sep, 2026
English
Check the availability with the operator
Departure on request
From:
US $1,678 per person
Multiple Room Types
Sign up and save
From Monday
7 Sep, 2026
To Monday
14 Sep, 2026
English
Check the availability with the operator
Departure on request
From:
US $1,792 per person
Multiple Room Types
Sign up and save
From Monday
14 Sep, 2026
To Monday
21 Sep, 2026
English
Check the availability with the operator
Departure on request
From:
US $1,792 per person
Multiple Room Types
Sign up and save
From Monday
21 Sep, 2026
To Monday
28 Sep, 2026
English
Check the availability with the operator
Departure on request
From:
US $1,792 per person
Multiple Room Types
Sign up and save
From Monday
28 Sep, 2026
To Monday
5 Oct, 2026
English
Check the availability with the operator
Departure on request
From:
US $1,792 per person
Multiple Room Types
Sign up and save
From Monday
5 Oct, 2026
To Monday
12 Oct, 2026
English
Check the availability with the operator
Departure on request
From:
US $1,792 per person
Multiple Room Types
Sign up and save

Why book with TourRadar?

Trusted and vetted operators
Rated excellent on
Best price guarantee

24/7 customer support
Earn $50 in travel credits

To protect your payment and ensure your booking will be processed in United States, 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

US $1,678 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 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 October 24th, 2026 a full payment is necessary. For tours departing after October 24th, 2026, a minimum payment of $450 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.
People also viewed
African Safari
Egypt & Jordan
Countryside of the Emerald Isle (Dublin to E…
Angola Highlights
Mediterranean Sailing Tours
Baltic Bike Tour: Tallinn to Vilnius (self-gu…
6-Day Best of Grand Alaska Highlights over 50…

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

Itinerary

Cortona

Included Activities

Optional Activities

Lake Trasimeno

Included Activities

Optional Activities

Pienza

Included Activities

Optional Activities

Val d'Orcia

Included Activities

Optional Activities

Montalcino

Included Activities

Montalcino

Included Activities

Optional Activities

Siena

Included Activities

Siena

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?

Good to Know

Keep Exploring Italy

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

Itinerary

Included Activities

Optional Activities

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?

Earn while you share

Good to Know

Keep Exploring Italy

Like this Moment?