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Experience the Cortona to Siena Cycling Tour, a breathtaking self-guided bike tour through the heart of Tuscany. Ride past rolling vineyards, medieval villages, and stunning landscapes, including the UNESCO-listed Val d'Orcia. This cycling holiday offers the perfect balance of exploration and relaxation, with multiple two-night stays to immerse yourself in Italy’s rich history, culture, and cuisine.
Pedal through charming hilltop towns like Cortona, Montepulciano, Pienza, and Montalcino, discovering their Renaissance architecture, local wineries, and artisan shops. Savor Brunello di Montalcino, Vino Nobile, and traditional Tuscan dishes as you cycle through iconic landscapes. From the shores of Lake Trasimeno to the medieval streets of Siena, each day offers scenic rides, historical landmarks, and unforgettable experiences. Whether you're cycling past cypress-lined roads, historic abbeys, or picturesque farmhouses, this Tuscany bike tour is an unforgettable way to explore one of Italy’s most spectacular regions.
Cortona to Siena Cycling Tour
Experience the Cortona to Siena Cycling Tour, a breathtaking self-guided bike tour through the heart of Tuscany. Ride past rolling vineyards, medieval villages, and stunning landscapes, including the UNESCO-listed Val d'Orcia. This cycling holiday offers the perfect balance of exploration and relaxation, with multiple two-night stays to immerse yourself in Italy’s rich history, culture, and cuisine.
Pedal through charming hilltop towns like Cortona, Montepulciano, Pienza, and Montalcino, discovering their Renaissance architecture, local wineries, and artisan shops. Savor Brunello di Montalcino, Vino Nobile, and traditional Tuscan dishes as you cycle through iconic landscapes. From the shores of Lake Trasimeno to the medieval streets of Siena, each day offers scenic rides, historical landmarks, and unforgettable experiences. Whether you're cycling past cypress-lined roads, historic abbeys, or picturesque farmhouses, this Tuscany bike tour is an unforgettable way to explore one of Italy’s most spectacular regions.
Ride through Tuscany’s stunning landscapes, medieval villages, and rolling hills, with stops for wine and local delicacies.
Taste world-famous Brunello di Montalcino, Vino Nobile, Pecorino cheese, and traditional Tuscan cuisine along your journey.
Explore charming towns like Cortona, Montepulciano, Pienza, and Siena, each rich in history, culture, and breathtaking views.
Pedal scenic roads past vineyards, olive groves, and cypress-lined paths, with flexible route options for all levels.
Trip map
Barbara C.
Amalfi Coast Bicycle Tour
We went through 10Adventures not familiar with them at all, and it was the best decision we ever made!
Allyson K.
Everest Base Camp
Just an amazing experience. Absolutely lifechanging!
Amy D.
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It was a fantastic trip and Nadine was extremely responsive to all of our questions.
Andrea S.
Full Via Rhona
We loved that we could easily customize the trip and add a couple of extra days in Geneva, in Lyon, and finally in Orange.
Andrea M.
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Our trip was great, we had an amazing time, and I highly recommend 10Adventures.
Andrea M.
Ladakh - Markha Valley Trek
Very kind, very helpful, attentive, and they took care of everything for us!
Andrew C.
Portuguese Camino Cycling Tour
Thank you 10Adventures, especially Nadine Gravis for all your help and support.
Becky M.
Camino Portugues
It was a fantastic experience from beginning to end!
Beth K.
Munich to Venice Cycling Tour
We were well supported and route directions were easy to follow!
Beverly M.
Munich to Venice Cycling Tour
We were well supported and route directions were easy to follow!
Bill B.
Torres del Paine O and W Circuit
10Adventures arranged everything for us, and what a trip it was!
Bipin J.
Tour du Mont Blanc
We stayed in the best hotels, enjoyed delectable food, and hiked over 100km. Thanks to 10Adventures for making a memorable trip!
Bryn T.
Camino de Santiago (from St Jean de Pied a Port)
It's been superbly organized by 10Adventures all the way.
Carol L.
Portuguese Camino in Deluxe Hotels
This trip had been on both of our bucketlists for a long time; however, we had no idea how to start it and what to do, until we found 10Adventures.
Carol V.
Camino Portuguese
Thank you 10Adventures, it was indeed a buen camino!
Catharine T.
Loire Valley: The Land of Castles Cycling Tour
We had an incredibly magical time that will stay with us for a lifetime.
Charmain C.
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A bucketlist experience, it was out of this world!
Chris N.
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10Adventures sorted out all of my accommodations and itinerary, and everything went as smooth as silk.
Christie O.
Camino de Santiago (English Way)
It was perfect! I liked the fact knowing that I had somebody to call if I needed any assistance.
Colleen N.
9-Day Self-Guided Rhône River by Bike Tour
This was a fantastic trip due to the flexibility offered to us by Nadine, our booking agent.
Craig and Ali C.
Cinque Terre 7 day Pilgrimage to Portovenere
Thank you so much 10Adventures! It was amazing and we're really looking forward to booking our next adventure with you.
Denise O.
Camino Francés 100km
The trip itself was mindblowing and better than we could have ever expected
Dorian H.
3 Day Aurora Borealis
I had a great trip with 10Adventures!
Doug H.
Dingle Peninsula Cycling Tour and Alpe Adria Cycle Path Tour
We chose 10Adventures because they are a very simply run, but reasonably priced and very well-organized organization.
Drew S.
9-Day Self-Guided Rhône River by Bike
10Adventures was awesome!
Eloise R.
Loire Valley: The Land of Castles Cycling Tour
Our entire trip was very well organized, and we had very detailed instructions we could always resort to.
Euan D.
Cycling Dolomites to Lake Garda
Cycling Dolomites to Lake Garda
Gisèle S.
Porto to Lisbon Cycle Tour
We couldn't have done this trip without Nadine's help! We had a couple of challenges and she helped us out.
Guri-Lise H.
Cycling from Porto to Lisbon Tour
Wonderful picnics!
Holly A.
Piedmont Val Maira Walking Tour
I cannot recommend the tour and 10Adventures enough!
Jeanne G.
7 Day camino De Santiago (in luxury 😊)
Nadine was my travel guide and expert, and she was wonderful!
Jennifer W.
9 day multisport adventure in Greece
10Adventures took care of everything!
Jillian R.
12 Night Hiking and Camping Through Canadian Rockies
Truly the trip of a lifetime!
Jinny M.
Self-Guided Alpilles of Provence Cycling Tour
We loved getting our luggage carried and we loved that it was all organized for us!
Aisling G.
Picos de Europa
Really good value for the money, and having booked it I won't be doing any organizing myself any more.
Alexander R.
Camino de Santiago, English route
We had a great time. The tour was very well organized, we stayed in nice places, and made some friends along the way.
John D.
Venice to Croatia Bike Tour
Great hotels, good breakfast every day, and good maps that always got us where we needed to go.
John O.
Camino Frances Saint-Jean-Pied-de-Port to Logrono
The price was far better than all of the other companies we had looked at.
Julieanne M.
The Complete TMB
All we had to do was show up, read the wonderful packet, and use the app that they provided. Such a weight off my shoulders!
Karen J.
Tour du Mont Blanc
We're ready for our next adventure!
Katarina P.
Walking in Val d’Orcia: Montepulciano to Siena
The trip was absolutely beautiful. I can't wait to go back!
Kate D.
Cotswolds Self Guided Bike Tour
It was a dream. I can't think of a better way to see the world!
Kellie C.
Laugavegur Trail
This was a dream trip for us and Nadine at 10Adventures planned it out to perfection.
Kelly D.
Custom Greece Tour
From the very beginning, the folks at 10Adventures - Richard and his team - took care of every single detail.
Kelly R.
Canal Du Midi Bike Tour
10Adventures did a fabulous job of planning!
Kevin N.
Rhone River Cycling Customized Trip
Great trip; we all throroughly enjoed it!
Kimberley D.
Camino Frances in Luxury
I didn't have to worry about a thing! Nadine and the team are amazing, I highly recommend them!
Kirsten S.
Il Primitivo
The whole process was great! Nadine helped us figure out where we wanted to go and how to block out the trip.
Lavern G.
Aurora Borealis Tour
The experience was just so wonderful!
Lee B.
Discover Quebec Self-Drive Tour
It was an awesome adventure!
Leslie L.
Cycle Venice, Italy to Porec, Croatia
From the initial inquiry right through to completion of the trip, the friendly staff was super efficient and the tour went very smoothly.
Lisa R.
Alpine Crossing 2: Garmish to Merano Tour
10Adventures was able to have everything laid out for me and planned perfectly so that I could literally go from one guesthouse location to the next.
Marilyn W.
Portuguese Camino from Porto
It's an awesome adventure. Don't wait, take yours!
Martha M.
Tour du Mont Blanc
It was a lot easier going through 10Adventures, I honestly don't think we could have booked our trip without that support.
Maureen W.
Minho and Porto Cycling Adventure
Nadine was a great help in assisting us with some minor tweaks to the itinerary, and while we were there we found the organization, the planning, and support were brilliant.
Max W.
Piedmont Val Maira Self Guided Hiking Tour
Everything was super well-organized by 10Adventures, they were very accommodating and communicative
Michael S.
El Camino Primitivo
This was absolutely the trip of a lifetime!
Mei Ling H.
Camino Frances (Sep 23)
I would like to express my appreciation to 10Adventures for the incredible experience on my first Camino Frances
Michelle H.
Tour du Mont Blanc
Thanks 10Adventures!
Kellie C.
Tour du Mont Blanc
10Adventures was our obvious choice when we decided to hike the Tour du Mont Blanc.
Mike C.
Tour du Mont Blanc
This wasn't my first time travelling with 10Adventures, and it certainly won't be my last!
Nancy E.
Portugal Sintra-Cascais
Thank you 10Adventures for some unforgettable experiences!
Nicole G.
Porto - Lisbon cycling
It was absolutely beautiful! We loved the service from 10Adventures.
Rachel D.
Venice to Croatia Cycling Tour
Can't say enough good things about 10Adventures. Communication with Nadine as we planned was spectacular!
Reid C.
Kitzbuhel to Drei Zinnen
I had the pleasure of doing a 10Adventures trip this summer and it was honestly one of the most amazing experiences of my life.
Renee H.
Venice to Croatia
We're just really appreciative of the experience and all of the help that the team gave, it was super smooth.
Renee S.
Tour du Mont Blanc
The accommodations that they booked for us were amazing, better than we would have picked on our own!
Rich G.
Patagonia O Circuit
Nadine and 10Adventures were just fantastic in setting up the trip and all of the logistics
Robert P.
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Highly recommend the 6-Day Moselle tour with 10Adventures.
Roberta F.
Camino de Santiago
10Adventures have been amazing communicators!
Rodney P.
Full Via Rhona
We had a fantastic time! The bikes were excellent
Sarah C.
X-Country Skiing in the Dolomites
We had a wonderful time, in no small part due to the wonderful support that 10Adventures gave us.
Sawyer P.
Full Via Rhona
Very amazing and very scenic!
Lesley C.
Discover Quebec Self-Drive Tour
Thank you Nadine for coordinating our discover Quebec trip!
Shahryar T.
8 Day Hike the Alpe Adria Trail Tour
Nadine and Richard have been outstanding in the way they have met our specific requirements and the flexibility they have shown.
Shelley S.
Ecuador Volcano Trek
Wonderful guides, the trip was well-organized, the food was delicious
Skye L.
Walking the Camino
Every step I took was really magical, and it was a lifechanging adventure.
Stacey C.
Dolomites to Lake Garda
Having retired from professional sport a couple of years ago, it was just exactly the challenging adventure that I needed.
Sue W.
Dana to Petra Jordan
I can't even describe it, it was so wonderful!
Svetlana L.
Alta Via Dolomites
The experience of planning the trip was outstanding!
Sylvia F.
Porto to Lisbon Bike Tour
It was all a fantastic experience, and a lot of it was due to the support and good service that was offered from Nadine from 10Adventures.
Teresa B.
West Highland Way 7 Day Hike in Scotland
10Adventures answered all of my email questions fast and promptly, and even checked in with us when we were on our hike to see how we were doing.
Timothy K.
Vanoise Loop
I couldn't be happier with how things turned out, specifically Nadine helped me before, after, and during the hike.
Tony W.
Slower Pace Camino de Santiago
Just like my first camino, all I have to worry about are my feet. Thanks 10Adventures!
Uwe P.
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The contact with 10Adventures, especially with Nadine, was excellent and very personal
Vanessa V.
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10Adventures took care of every detail!
Wai Lee Y.
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It was an exhiliarating and awesome experience that exceeded all my expectations!
Why book with 10 Adventures?
We know adventure
Founded by experienced travellers, active and adventure vacations are all we do.
Experience the trip of a lifetime organized by a team of travel specialists who combine knowledge and passion for adventure travel.
Self-guided specialists
With over 600 tours across 30+ countries, we specialize in self-guided tours.
Combine the freedom of travelling on your own with the confidence that all of your logistics are taken care of.
Packed with value
Get everything you need for your next vacation with one easy booking.
We take care of accommodations, luggage transfers, gear rentals, and more - so you can focus on making memories.
World Class support
Get unbeatable support at every step of your journey.
Whether you are planning or travelling, no matter what your question, a real human is always a call or click away.
Hassle free bookings
Have peace of mind for when travel plans change.
Explore our flexible booking, payment, and cancellation options, as well as our Lifetime Deposits program.
2+ Travellers
Solo Travellers
| Dates | 2+ Travellers | Solo Travellers |
|---|---|---|
| Low Season | ||
| Mar 1, 2025 to Apr 30, 2025 | $1,650USD | Inquire |
| Jun 16, 2025 to Aug 31, 2025 | $1,650USD | Inquire |
| Oct 16, 2025 to Oct 31, 2025 | $1,650USD | Inquire |
| High Season | ||
| May 1, 2025 to Jun 15, 2025 | $1,775USD | Inquire |
| Sep 1, 2025 to Oct 15, 2025 | $1,775USD | Inquire |
| Optional Extras | ||
| Single Supplement$350USD | ||
Meals
7 breakfasts are included.
Accommodations
Accommodations for 7 nights are included. Additional nights before and after the tour are not included but can be added as a supplement.
Transportation during the Tour
Luggage transfers are included throughout the tour.
Also included
- Route Information that can be accessed through digital mobile app
- Excursions mentioned in the itinerary
- Bike fitting and briefing in English by our professional staff at tour start
Not included
- Flights
- Meals, drinks, or snacks not previously mentioned
- Gratuities for tour guides or other staff if desired
- Entrance to museums or other activities not indicated as included
- City hotel tax
- Insurance
- Bicycle rental
Optional Extras
- Additional nights before or after the tour
- Single occupancy upgrades
- Optional activities or excursions
-
- Wine Tasting in Montalcino
- Guided visit of Siena
- Cooking Class
- Bike Rental
-
- Aluminum hybrid: €170
- Premium Titanium road or hybrid: €215
- Touring E-bike (hybrid with straight handlebar): €295
Accommodation for Cortona to Siena Cycling Tour
This tour is based in Hotels. Hotels on this trip are 3 and 4-star and offer modern conveniences that can make this trip more pleasant. Rooms may include amenities such as a minibar, concierge service, and a city view.
Single Rooms and Solo Travellers
Rooms are based on double occupancy. A single supplement is available for a private room when possible. Solo travelers may need to pay an additional fee.
How hard is the Cortona to Siena Cycling Tour?
We rate this tour a 3/5 difficulty. With multiple-night stays, you’ll have the flexibility to choose between longer or shorter rides, with each day featuring some hills, allowing you to decide the distance and number of climbs based on your preference.
Do I need a visa to travel to Italy?
Check with your local country about visa requirements. You could also try this website, though you should verify with your government.
Are meals included on the Cortona to Siena Cycling Tour?
7 breakfasts are included.
Do I need insurance?
Yes, it is mandatory to have health and medical insurance to join this trip, and your insurance should cover cycling. Get your travel insurance.
How do I get to Cortona to start this tour?
To get to Cortona from Florence Airport, take a 30-minute trip to the main train station, Firenze S. Maria Novella, by either shuttle bus or taxi. If you choose a taxi, make sure to agree on the fare beforehand, plus any luggage fees. The ride typically takes around 15–20 minutes, depending on traffic. Alternatively, you can take one of the several trains running daily between Florence and Cortona, with the journey usually lasting about 1 hour and 30 minutes.
Is the Cortona to Siena Cycling Tour in English?
This is a self-guided tour without guide services, but all tour materials are provided in English.
Where does the Cortona to Siena Cycling Tour end?
Your tour concludes in Siena.
Do I need special vaccines to travel to Italy?
Check with your family doctor.
Are there any travel restrictions for Italy?
Please check with your local government about travel restrictions before you book your tour. This map from the US Department of State provides an overview of the current status in countries around the globe. The UK‘s Foreign Office and Government of Canada also provide advice on foreign travel. Note that the travel advice may change depending on your nationality.