The Da Vinci Road
10 Night GPS Self Guided e-Bike Adventure in Tuscany

Ride through Da Vinci's Tuscany
and Take Your Time with the 10 Night & 11 Day Cycling Adventure
2019 marked 500 years since the death of Leonardo da Vinci and the legacy of the Tuscan engineer, artist and genius is still very visible today.
Prices from $2,205 per person – View Prices
Summary
- 11 Day | 10 Night
- 🍽 Bed & Breakfast
- An e Bike Experience in Italy
- 🍇 Classic Tuscan Scenery | Montepulciano Vineyards | Val d'Orcia | Crete Sinesi
- 🏰 Stay in a Tuscan Castle & Tuscan Villas
- 🍷 Super Tuscan Wines: Montepulciano | Montalcino | Chianti
- 🧭 Turn-by-Turn GPS Navigation
- 🧳 On Tour Luggage Transfer
- 😊 Smaller, Family-Run Hotels & Country Houses
- Start & Finish | Cortona, Tuscany
- 🚴♂️ Raleigh Motus Grand Tour Low Step Electric Bike with Bosch Active Line Plus & Battery Range 135 miles
Statistics
- ACTIVITY LEVEL: Easy/Moderate
- AVERAGE SADDLE TIME: 2h 39m
- MINIMUM DISTANCE: 151 miles
- MINIMUM CYCLE DAYS: 6
- TOTAL SADDLE TIME: 13h 14m
- POSSIBLE CYCLE DAYS: 9
- REST DAYS: 3 [optional]
- CALORIES BURNED 4000 approx
Day by day
Your journey touches significant moments from the life of Leonardo da Vinci. Many traditions, buildings and even the Tuscan way of life, remain much as they were in Da Vinci’s time.
With your luggage transferred to your next destination, you travel light, leaving you free to think only of the road before you.
- CLICK ON EACH DAY TO DISCOVER MORE -
Day 1: Arrival
It begins with the most wonderful cypress-lined driveway that you've ever disappeared into! Every bike tour in Tuscany should begin and end this way.
A piece of 'la dolce vita' or as we know it Villa di Piazzano.
Highlights
★Villa di Piazzano ★Under the Tuscan Sunset
Statistics
Swimming Pool - 1
Accommodation
Villa di Piazzano, Cortona, Italy
La dolce vita' or as we know it Villa di Piazzano.
Find out more:
Travellers Tales article
Day 2: From Cortona to Montefollonico
Cycling through the Val di Chiana is easy thanks in no small part to Leonardo da Vinci. Having mapped the area, his work enabled a network of drainage channels to be dug leaving the fertile terrain that you see today. Sunflowers stand alongside vines, wheat and olive trees.
Montepulciano and the vineyards producing the famous Vino Nobile are en route. In Montefollonico visit Cantine Innocenti and taste his Vino Nobile! Ask to visit the terrace and take a glass of something with you. The view back to Cortona is jaw-dropping. If you’d like to continue the wine theme over dinner, try Ristorante Osteria La Botte Piena in the centre of the village.
Highlights
★Valdichiana ★Montefollonico
Statistics
Miles: 23 | Saddle Time: 2h 5m | Difficulty: 🚲
Accommodation
La Chiusa Hotel & Restaurant, Montefollonico
La Chiusa is a few steps from the edge of this wonderful medieval town. Be sure to visit Cantine Innocenti
Find out more:
Travellers Tales article
Day 3: From Montefollonico to San Quirico d’Orcia
The Monastery of S. Anna in Camprena, was the setting for the film ‘The English Patient'.
Prior to which a spend a few minutes in the hill-top villages of Petroio and Castelmuzio.
Your arrival in San Quirico d’Orcia through the gate perfectly sets the expectation for this wonderful stop and a special hotel.
Highlights
★Visits to Petroio & Castelmuzio ★Monastery of Santa Anna in Camprena
Statistics
Miles: 18 | Saddle Time: 1h 38m | Difficulty: 🚲
Accommodation
Dimore del Capitano, San Quirico d’Orcia
Dimore del Capitano is at the very heart of San Quirico d'Orica is this wonderful little hideaway.
Find out more:
Travellers Tales article
Day 4: To Bagno Vignoni, Montalcino & San Quirico d'Orcia
Take a Rest Day or...
... enjoy the recommended adventure - a stunning 30-mile ride through the Val d'Orcia.
The views as you cycle from San Quirico, are just absolutely captivating.
Around these parts are where they filmed scenes from Gladiator. Stop at the spa village of Bagno Vignoni, for coffee. Then ride and roll through this classic Tuscan countryside towards Montalcino.
SHORT ITINERARY ALSO AVAILABLE
Highlights
★Bagno Vignoni ★Views of Val d'Orcia ★Montalcino
Statistics
Miles: 30 | Saddle Time: 2h 53m | Difficulty: 🚲🚲
Accommodation
Dimore del Capitano, San Quirico d'Orcia, Tuscany
The sweeping views across the Val d'Orica - classic Tuscan terrain
Find out more:
Travellers Tales article
Day 5: From San Quirico d’Orcia to Castello di Leonina
Ease into your day with a long, steady cycle ride down-hill.
A gentle days cycling through a gradually changing countryside. Leaving the rolling beauty of the Val d'Orcia for the dramatic Crete Senesi - the clays of Siena.
Stop in Asciano for lunch - a pizza from the wood fired oven, maybe!
Highlights
★Crete Senesi ★Asciano ★Castello di Leonina
Statistics
Miles: 28 | Saddle Time: 2h 29m | Difficulty: 🚲
Accommodation
Castello di Leonina, Asicano, Tuscany
Pull up a chair and watch the Tuscan sun sink behind Siena from one of the best vantage points in Tuscany
Find out more:
Travellers Tales article
Day 6: OPTION Ride to Siena
Take a Rest Day or...
Siena is just 12 Km from Castello di Leonina and so worth a visit whether by bike or taxi.
As the traffic in Siena can be busy, you need to exercise a little extra care.
Highlights
★Siena
Statistics
Miles: 28 | Saddle Time: 2h 9m | Difficulty: 🚲
Accommodation
Castello di Leonina, Asicano, Tuscany
Stunning views across the Crete Senesi from Castello di Leonina
Find out more:
Travellers Tales article
Day 7: From Castello di Leonina to Liverano, Radda in Chianti
Once again, the Tuscany countryside changes dramatically from the Crete Sinesi to the oak woods and vineyards of Chianti. The often breathtaking scenery will have your camera clicking like a wood pecker!
Simone will serve you a the most memorable lunch at Ristorante Malborghetto believed to be one the top ten restaurants in Tuscany, I kid you not.
Highlights
★Ristorante Malborghetto ★Chianti Vines
Statistics
Miles: 23 | Saddle Time: 2h 3m | Difficulty: 🚲🚲
Accommodation
CDH Hotel Radda in Chianti, Tuscany
I challenge you not to fall completely head over heels with Radda in Chianti!
Find out more:
Travellers Tales article
Day 8: Rest Day or ride to Villa Vignamggio via Greve in Chianti
Take a Rest Day or...
Villa Vignamaggio is a spectacular villa.
Said to be the summer home of Mona Lisa and visited often by Leonardo da Vinci. Greve in Chianti is one of those places not to be missed. It is the centre of the Chianti wine world. Stroll around the piazza, choose somewhere for lunch and just drink in the atmosphere.
Highlights
★Villa Vignamaggio ★Greve in Chianti ★Chianti Classico
Statistics
Miles: 23 | Saddle Time: 2h 3m | Difficulty: 🚲🚲
Accommodation
CDH Hotel Radda in Chianti, Tuscany
Taste the wines of Radda. Whether you take a rest day here or take a ride it is one of those places you always speak of!
Find out more:
Travellers Tales article
Day 9: From Radda in Chianti to Lucignano
There is nothing quite so enjoyable as a long downhill, freewheel on a bike.
Plenty of that today!
A few climbs admittedly but the net is a height loss. Enjoy the saddle time. Stop for a coffee in Castelnuovo Berardenga and you could drop by the Fèlsina vineyard. Very nice wines!
Highlights
★Long Downhill ★Castelnuovo Berardenga
Statistics
Miles: 37 | Saddle Time: 3h 13m | Difficulty: 🚲
Accommodation
Le Caselle Ristorante Il Baraccotto, Lucignano
Simplicity and beautifully presented.
Find out more:
Travellers Tales article
Day 10: From Lucignano to Cortona
Leonardo da Vinci arrived in Foiano in 1502 and began to draw up plans for the draining of the Valdichiana and in the process creating the famous map of Valdichiana.
Imagine him standing atop the campanile in the centre of town sketching all that he surveyed.
Highlights
★Freewheeling ★Views of Cortona ★Valdichiana
Statistics
Miles: 21 | Saddle Time: 1h 46m | Difficulty: 🚲
Accommodation
Villa di Piazzano, Cortona, Italy
Slip off the padded shorts and into your Speedos, for the pool awaits! Maybe spend the evening in Cortona?
Find out more:
Travellers Tales article
Day 11: Departure Day
Your final morning. Take breakfast by the pool and maybe take a cappuccino in Cortona before departing!
Highlights
★ Breakfast on the terrace
Journey Map
Best Bits
- Stay on a Vineyard
- Wine Regions & History
- Wonderful accommodation - Castles, Villas & Vineyards
- Quiet Country Roads
- Val d'Orcia | Crete Sinesi | Chianti
- Truly Outstanding Scenery
- electric Bike Tour in Tuscany
The Da Vinci Road FAQ's
“Cycling to be Enjoyed, Not Endured”
Here, we try to cover some of the more often asked questions ...
- Am I fit enough? The Da Vinci Road bike tour requires just over 2hrs cycling per day. eBikes do not give you a free ride. You need to pedal. While the eBike makes things much easier, you still require a reasonable level of fitness. The fitter you are, the greater your enjoyment. The oldest person that we have had is Geoffrey who at 84 years of age. The youngest was 12 years.
- How busy are the roads? Italian roads tend to be much quieter than people are used to. The vast majority of your itinerary is along quiet country roads. There is one exception - on day 3 [optional ride] the final 4Km or so is on a wide, fast road with a wide hard shoulder.
- I haven't ridden a bike for a while, but I'd like to come on an eBike trip. That's fine. We strongly recommend that you put in a little time on a bike before you come. The fitter and more comfortable you are on a bike, the more you will get from your vacation. In fact, comfort is the main thing - get used to sitting on a bike!
- My Luggage - whats happens to it? Each transfer day sees your luggage moved by our support vehicle from one hotel to the next. We provide you with luggage labels.
- What should I wear? Our eBikes have a very comfortable Gel Saddle and a suspension seat post. Despite this, you might choose to wear padded cycling shorts/skirts for extra comfort. Our eBike Leaders wear padded underwear, which we think is more flexible than the padded short. You can then choose to wear this with your favourite shorts. And yes, there are ladies versions too! You do not need a whole wardrobe of special cycling clothes! A few well-chosen items will help keep you cool/warm and comfortable on your eBike trip. Sun cream and a neckerchief or scarf are a very good idea.
- Footwear - You need a pair of shoes that are resistant to weather and have a good grip. They should also be comfortable for walking. Our eBikes do not use the cleat system.
- Do you provide Helmets? Yes, we provide helmets. Its included in the price.
- Do I have to wear a helmet? No, you don't. It is not a legal requirement to wear protective headgear. If you choose not to wear a helmet, that is entirely your own decision and choice.
- What is provided with the bike?
- - Water Bottle & Holder - Each bike is equipped with a handlebar-mounted water bottle holder and water bottle.
- - A Rear View Mirror is fitted on the bike to help you keep the group together and improve safety.
- - Pannier - each bike is fitted with a single safari pannier. There is sufficient room for a wallet, cameras, sun cream etc.
- - Wet Weather Cape - yes, it does rain, occasionally. We provide a high-quality bike cape for each rider.
- - Battery Charger - each bike has a battery charger.
- - Power Adapter - to make charging easier.
- - Spare Inner Tube - we don't expect you to fix punctures. We provide a replacement inner tube.
- - Pump - you have a small, portable pump for roadside emergencies. Each hotel keeps a large air pump.
- - Hi-Visibility Jacket - in case of roadside maintenance, we provide you with a Hi-Vis jacket.
- - Security Cable - to lock your bike.
- Your Guide also carries...
- - BOSCH Nyon GPS
- - Tool Kit
- - Basic First Aid Kit
- What should I carry with me?
- - Passport
- - Insurance Documentation
- - Cash for the day
- - Credit/Debit Cards
- - Change of clothing to anticipate changes in weather
- What is the best time of year to take an eBike Safari? Great question. We have written a whole piece on this - CLICK HERE




Price
$2,205 per person
Your adventure includes:
Your adventure includes:
- 11 Days | 10 Nights
- Bed & Breakfast | Half Board Option
- Quality Accommodation | See itinerary for full details
- Welcome Drinks, Briefing, Bike Set-Up
- BOSCH Nyon GPS | Simple, Easy-to-Use Turn-by-Turn Guidance
- Start & Finish - Cortona, Tuscany
- On-Tour Luggage Transfer
- Custom Inspired Raleigh Electric Trekking Bike
- 24/7 WhatsApp Guide & Emergency Vehicle Support
More Cycling Adventures in Tuscany & Umbria
“Thanks to being able to saunter up the hills – and the ebikes really do allow this – day trips of 40 or 50 miles are not onerous.”