Tuscany for Wine Lovers: Terroir of Tuscany🍷🍇

The Very Best of Tuscany's Wine Regions

Brunello 🍷 Vino Nobile di Montepulciano 🍷 Chianti

⭐️ The Sunday Times, Best Cycling Breaks

When Marco Molesini proudly declares that, "in Italy, God makes the wine," he should add that God has paired Tuscany's wines with some truly remarkable 'cycling terroir'.

It is not only the Tuscan wines that have 'good legs'. The Bosch pedal-assist power of your eBike means you have 'good legs' too, while the gel saddle will soften your 'Palate'. The Tuscan cycling terroir is as spicy and lingering as the famous Brunello di Montalcino.

☀️ Cycling to be Enjoyed, not Endured ☀️


Prices from $3,596 per person View Prices


  • Tuscany's Best Cycling Terroir
  • 8 Day | 7 Nights
  • 🍷 5 Wine Tastings including Italian wine tasting & orientation by sommelier Marco Molesini, Cortona
  • 🍷 Wines: Vino Nobile di Montepulciano | Brunello di Montalcino | Chianti Classico
  • 🍇 Stay two nights on the Livernano Vineyard
  • The Legend of Mona Lisa & Vignamaggio
  • Visit scenes from ... the Gladiator, The English Patient, Much a Do About Nothing & Under the Tuscan Sun
  • Distinctive Accommodation & Memorable Meals
  • Luggage Transfers included
  • Small Groups | Max 8 per group
  • ✤ FULLY GUIDED itinerary & Guarantee of Quality Accommodation ✤
  • Customised Raleigh Motus Grand Tour electric Bike with Bosch Pedal Assist


  • ACTIVITY LEVEL: Moderate
  • TERRAIN: Tuscany is 92% Hills
  • CYCLING PER DAY: 3 to 4 hrs
  • DISTANCE: 160 miles
  • CYCLE DAYS: 4 (+2)
  • MAXIMUM TOTAL DISTANCE: 240 miles | 365 Km (6 cycle days)
  • TOTAL SADDLE TIME: 19 hours
  • AVERAGE DAY: 40 miles
  • CALORIES BURNED 7000 approx
  • Tripadvisor READ OUR REVIEWS

Day by day

With your luggage transferred to your next destination for you, you travel light, each and every day, leaving you free to think only of the matter in hand.



Day 1: Arrival

The cypress-lined driveway leading to Villa di Piazzano, Cortona seems to brush away the memories of whatever you were doing yesterday.

Then meet sommelier Marco Molesini. He will set your palate for the week ahead with his private wine lesson and orientation.


★Villa di Piazzano ★Under the Tuscan Sunset ★Streets of Cortona


Wine Tasting & Education


Villa di Piazzano, Cortona | ✧✧✧✧

Villa di Piazzano, Cortona | Al fresco dining at its very best

Find out more:
Travellers Tales article

Day 2: The Most Noble Wines

To San Quirico d'Orcia

Leaving the Balcony of Tuscany behind, venture across the Valdichiana, riding through by the vines of Montepulciano.

An extra-ordinary lunch in beautiful Montefollonico, setting the scene for our afternoon visit to Sant'Anna in Camprena, where scenes from The English Patient are set.

The ride to San Quirico d'Orcia through classical Tuscan scenery will stay with you as a life long memory.


★Montefollonico ★Sant'Anna in Camprena ★Amazing Tuscan Views


Miles: 34 | Average Speed: 12.4 mph | Saddle Time: 3hrs 25min | Wine Tastings: 🍷| Difficulty: 🚲


Villa del Capitano, San Quirico d'Orcia | ✧✧✧✧

This Hotel made my road trip so perfect. I was right in the centre. Super clean and well designed. A warm welcome and very good hospitality...

Find out more:
Travellers Tales article

Day 3: Brunello and your eBike

To Bagno Vignoni, Montalcino & San Quirico d'Orcia

The views as you leave San Quirico, are absolutely captivating.

Then, just as you can't imagine it getting any better, you ride right into the middle of scenes from the Hollywood blockbuster 'Gladiator'.

At the spa village of Bagno Vignoni, grab a coffee as you marvel at the natural waters.

Brunello & your eBike - A history of modern Italian bike racing, lunch and a taste of the Brunello Super Tuscan wine.


★The Ancient Spa ★The Wolves


Miles: 31 | Average Speed: 12.7mph | Saddle Time: 2hrs 29min | Wine Tastings: 🍷Vineyards: 🍇| Difficulty: 🚲🚲


Villa del Capitano, San Quirico d'Orcia | ✧✧✧✧

This hotel is in the magical heart of Val d'Orcia

Find out more:
Travellers Tales article

Day 4: Via Francigena | Meet the Pilgrims

To the outskirts of Siena

Meet smiling pilgrims as we ride along the Via Francigena - the famous pilgrimage route from Canterbury to Rome & Jerusalem.

Lunch in Asciano and an evening sunset over Siena in the heart of the Crete Sinese.


Miles 29 | Average Speed: 12 mph | Saddle Time: 2hrs 23min | Difficulty: 🚲


★Lunchtime Pizza from a wood fired oven ★Crete Sinese ★Views of Siena


Castello di Leonina, Siena/Asciano | ✧✧✧✧

Castello Leonina - watch the sunset over Siena

Find out more:
Travellers Tales article

Day 5: eBike into Chianti

To Radda in Chianti

The unmistakable Crete Sinese gives way to the oak woods of deepest Chianti.

Here, we gain our first taste of Chianti Classico.


★Vineyard views ★The Oak Forest


Miles: 31.6 | Average Speed: 11.4mph | Saddle Time: 2hrs 54min | Wine Tastings: 🍷 | Vineyards: 🍇🍇 | Difficulty: 🚲 🚲


Livernano, Radda in Chianti | ✧✧✧

Stay the night on the Livernano estate and vineyard

Find out more:
Travellers Tales article

Day 6: Mona Lisa & Chianti

To Greve in Chianti & back

A day to explore the depths of Chianti.

Visit the villa where Mona Lisa used to play in the gardens. Villa Vignamaggio was famously visited by the Kennedy's, Queen Elizabeth II and many more.

Oh and don't forget to taste the wines!


★Vignamaggio ★Greve-in-Chianti ★Radda-in-Chianti


Miles: 28.4 | Average Speed: 11mph | Saddle Time: 2hrs 47min | Wine Tastings: 🍷🍷 | Vineyards: 🍇🍇 | Difficulty: 🚲🚲


Livernano, Radda in Chianti | ✧✧✧

Surrounded by forests, vines and olive groves. In the heart of the Chianti Hills.

Find out more:
Travellers Tales article

Day 7: The Valdichiana

To Cortona

It's a long ride today, but mostly down-hill!

Whizzing through the vines, olive trees and a return to the wide open spaces of the Valdichiana and Cortona.


★Freewheeling for miles ★Trattoria Lunch ★Val di Chiana


Miles: 55.6 | Average Speed: 12.4mph | Saddle Time: 3hrs 43min | Difficulty: 🚲


Villa di Piazzano, Cortona | ✧✧✧✧

Built in the early 1500s by Cardinal Silvio Passerini, a protegè of the Medici’s, to serve as his hunting manor.

Find out more:
Travellers Tales article

Day 8: Cappuccino & Cortona

Before departure, take a coffee while drinking in the extra-ordinary gardens of Villa di Piazzano.


Villa di Piazzano Breakfast

Journey Map

“Ian and I loved your guided e bike holiday around Tuscany. It was beautifully organised with every little detail thought of, including the most perfect lunch stops and, of course amazing hotels!”

Sir Ian & Lady Collett

“I did endless research beforehand wondering whether it would work out as a holiday, was Italy the right spot and Inspired Italy the right company? All I can say all 8 of us loved it. There was a pretty wide range of fitness levels, but with the 4 speeds on the eBike it was not a problem.”

Nicola Odey on an Umbria eBike Safari

“Puts the joy back into cycling”

Graham Adamson, Canada - Guided Tuscany eBike Tour

Best Bits

  • Outstanding Vistas
  • Tales, Anecdotes & Shaggy-Dog Stories
  • Castles, Villas & Vineyards - Select Accommodation
  • Memorable Meals


“Cycling to Enjoyed ☀️”

Here, we try to cover some of the more often asked questions ...

  1. Am I fit enough? The Terroir of Tuscany eBike Safari requires 3 to 4 hours of 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.
  2. 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 - the final 4Km on day two.
  3. 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.
  4. 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.
  5. 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.
  6. 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.
  7. Do you provide Helmets? Yes, we provide helmets. Its included in the price.
  8. 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.
  9. 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 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.
  10. Your Guide also carries...
    •  - BOSCH Nyon GPS
    •  - Tool Kit
    •  - Basic First Aid Kit
  11. What should I carry with me?
    •  - Passport
    •  - Insurance Documentation
    •  - Cash for the day
    •  - Credit/Debit Cards
    •  - Change of clothing to anticipate changes in weather
  12.  What is the best time of year to take an eBike Safari? Great question. We have written a whole piece on this - CLICK HERE


$3,596 per person

Your adventure includes:

Your adventure includes:

  • 8 Days | 7 Nights
  • 🍽 MEALS: All Breakfasts, All Dinners & 2 Lunches including ...
  • A La Carte Dinners each and every night
  • Pizza Lunch from a Wood Fired Oven & Drinks 🍕
  • 🍇 Brunello & Chianti Vineyard Visits, Wine Tastings & Tours including...
  • 🍷 Brunello Wine Tasting, Tour & Light Lunch at Ciacci Piccolomini d'Aragona
  • 🍷 Chianti Wine Tasting at Livernano
  • 🍷 Wine Tasting & Orientation with sommelier Marco Molesini, Cortona
  • 🍷 Wines include Vino Nobile di Montepulciano; Chianti: Casalvento, Livernano & Vignamaggio; Brunello di Montalcino: Ciacci Piccolomini d'Aragona
  • Accommodation of Distinction & Memorable Meals
  • 🍇 Two Nights at Livernano Vineyard | Stay in a Tuscan Castle
  • 🚴‍♂️ Full Time Bike Leader
  • Start & Finish Villa di Piazzano, Cortona
  • On Safari Luggage Transfer
  • Customised Raleigh Motus Grand Tour electric Bike with Bosch Pedal Assist
  • Small Groups | Max. 8 Guests per Group + Leader
  • Wine Themed Gift & Keepsake
  • EXCLUDES: Flights & Transfers - we provide full planning pre & post trip support for airport transfers

More eBike 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.

Christian Wolmar

Once Upon a Time

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Umbria for Food & Wine Lovers: Our Umbria 🍷🍝

Niccone Valley | Montone | Gubbio | AssisiFULLY GUIDED
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  • • 🍷Tastings & 🍝 Cooking Lesson
  • • From $3,347 per person

Umbria for Wine Lovers🍷🍇

Explore & Delight in Umbria's Rural WineriesFULLY GUIDED
  • • ☀️ 6 Days | 7 Nights or 4 Days | 5 Nights
  • • 🍇 Umbria's Best Wine Tours & Tastings by Bike
  • • Easy Cycling
  • • From $3,296 per person

The Day I Saw Siena

Chianti | Siena | San Gimignano | VolterraFULLY GUIDED
  • • EASY CYCLING with some short moderate sections
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