Italy 19:33 – 18 November 2019

The Day I Saw Siena

⭐️NEW for 2020 | Fully Guided 8 Day 7 Nights

Fully Guided Ride through Siena, Chianti & San Giminiano

Visit Tuscany for the art, architecture, food & history, but get the most from its people

The Chianti towns of Greve, Radda and Lecchi set amongst contoured valleys and vineyards, vie for your Tuscany memories challenged by the unmistakeable Crete Sinesi towns of Siena, San Giminiano, Monteriggioni and Volterra. What a tussle it promises to be!


☀️ Cycling to Enjoy, Not Endure ☀️

Prices from $2,477 per person View Prices


  • 8 Days | 7 Nights
  • Full Breakfasts | Fiorentina Steak Night
  • A More Mature, Full Time Bike Leader
  • Small Groups | Max 8 Guests
  • Outstanding Scenery | History | Art | Food | Wine
  • A More Mature, Full Time eBike Leader
  • Two Wine Tastings & Lots of Wine Opportunities
  • Visits | Tours | Anecdotes
  • Luggage Transfers
  • ☀️FULLY GUIDED INDULGENCE Itinerary | Guarantee of Quality Accommodation


  • ACTIVITY LEVEL: Easy/Moderate
  • CYCLING PER DAY: 1h to 2hrs
  • MAXIMUM DISTANCE: 93 miles
  • TOTAL SADDLE TIME: 10hrs max
  • LONGEST LEG: 23 miles
  • AVERAGE DAY: Less than 20 miles
  • CALORIES BURNED: 3286 approx

Day by day


The short transfer from Firenze soon has you in the bosom of Chianti. You can, on occasion and at the right time of year, detect just the hint and essence of Sangiovese hanging in the air!


⭐️Chianti views


Hotel Sangiovese | Panzano in Chianti ✩✩✩

"..arriving at the pool area was like entering paradise. So peaceful and that gorgeous view."

Find out more:
Travellers Tales article

Day 2: Monna Lisa & Greve

At the very heart of Chianti is Greve where the awkwardly shaped piazza plays host to the regions premier wine festival.

This valley is dotted with history and acre upon acre of Chianti Classico vines.

Enjoy a visit to Villa Vignamaggio, where history blends tales of Leonardo Davinci, Mona Lisa, John F Kennedy and Queen Elizabeth II!


⭐️Villa Vignamaggio ⭐️Chianti Classico Wine Tasting ⭐️Lunch in Greve in Chianti


18.33Km | 1h 3m Saddle Time | Difficulty: 🚴🏼‍♂


Hotel Sangiovese | Panzano in Chianti ✩✩✩

"The 600 years old house is a romance itself .. "

Find out more:
Travellers Tales article

Day 3: A Ride Through Chianti

An easy ride to Radda in Chianti and time for a coffee and a wander around this single street, hill-top town.

From its quiet, unassuming and curiously quaint centre we drop into the backroads of Chianti towards Lecchi in Chianti and a lunch to remember. A short ride to San Sano and your overnight accommodation.


⭐️ Radda in Chianti ⭐️ Lecchi in Chianti ⭐️ Lunch


26.61Km | 1h 23m Saddle Time | Difficulty: 🚴🏼‍♂


Hotel San San | San Sano ✩✩✩

"The hotel is in a very little village away from everything."

Find out more:
Travellers Tales article

Day 4: Today Day You See Siena

Cast your gaze across the fields of the famed Antanori vines from your breakfast table.

Today we conquer Siena and ride to its very heart, Piazza del Campo famed for the Palio.

Leaving behind the hustle and bustle of Siena, we glide back into the Tuscan countryside and towards the most extraordinary evening stopovers - Monteriggioni.


⭐️Siena ⭐️Piazza del Campo


37.69Km | 2h 4m Saddle Time | Difficulty: 🚴🏼‍♂🚴🏼‍♂


Hotel Monteriggioni | Monteriggioni ✩✩✩✩

"The town is stunning and the hotel is homely and quaint."

Find out more:
Travellers Tales article

Day 5: The Towers of San Giminiano

Slip away through the ancient gate of Monteriggioni into the berceuse fields and throw a look back at your overnight location. Truly extraordinary!

A steady ride to San Giminiano today. We cycle to the heart of this wonderful town.

Personally, I cannot remove the image of Maggie Smith and Judy Dench here in the film ‘Tea with Mussolini’.

You’ll see what I mean, as the day trippers melt away and the evening piazza is left to the atmosphere of a lesser tempo, ‘più lento’ as they say.


⭐️Wheat fields of Tuscany ⭐️San Giminiano


37.14Km | 2h 3m Saddle Time | Difficulty: 🚴🏼‍♂🚴🏼‍♂


Hotel la Cisterna | San Giminiano ✩✩✩

"..a classic, old hotel with really nice, upgraded rooms. The location is right in the middle of the medieval town of San Gimignano

Find out more:
Travellers Tales article

Day 6: The Longest Descent

The ride from San Giminiano to Volterra is a great favourite.

Vast expansive vistas, the enormous freewheeling descent and even the climb to Volterra.

We will probably stop to have lunch just before the climb to Volterra. And this quiet, unassuming town has plenty of surprises.


⭐️Views of San Giminiano ⭐️The Longest Freewheel Descent


30Km | 1h 51m Saddle Time | Difficulty: 🚴🏼‍♂🚴🏼‍♂


Hotel San Lino | Volterra ✩✩✩✩

"Great location, clean and comfortable and a bonus having a pool. The rooms are a bit anonymous. But as former nuns' cells, perhaps they should be!

Find out more:
Travellers Tales article

Day 7: Volterra

Take a time to enjoy rural Tuscany and the history of this extraordinary town.

Founded in the 8th Century BC (yes, its 2,800 years old) visit the ancient Roman theatre, the piazzas and a local lunch.

The hotel pool is very inviting too!

OPTIONAL: Short Ride available on request


⭐️ Views of Volterra


Rest Day | Optional Loop Ride


Hotel San Lino | Volterra ✩✩✩✩

Day 8: Departure

After that breakfast, say 'ciao and arrivederci to your bike leader and head off to you next location ... Pisa, Firenze or Rome!


Ciao, baci e abbracci!

Journey Map

FAQ's - The Day I Saw Siena

“Inspired Italy exceeded our expectations providing us with a lifetime of memories of beautiful cycling scenery, fairytale medieval towns, fabulous meals, fantastic wine tours and beautiful, intimate boutique hotels.”

  1. Am I fit enough? The Day I Saw Siena eBike adventure requires 2 to 3 hours 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 when descending from the Assisi. The first 3 or 4 miles (30 mins maximum) is busier.
  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 see 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 head gear. If you choose not to wear a helmet, that is entirely your own decision and choice.
  9. What is provided with the bike?
    1. Water Bottle & Holder - Each bike is equipped with a handle bar mounted water bottle holder and water bottle.
    2. A Rear View Mirror is fitted on the bike to help you keep the group together and improve safety.
    3. Pannier - each bike is fitted with a single safari pannier. There is sufficient room for wallet, cameras, sun cream etc.
    4. Wet Weather Cape - yes, it does rain, occasionally. We provide a high-quality bike cape for each rider.
    5. Battery Charger - each bike has a battery charger.
    6. Power Adapter - to make charging easier.
    7. Spare Inner Tube - we don't expect you to fix punctures. We provide a replacement inner tube.
    8. Pump - you have a small, portable pump for road side emergencies. Each hotel keeps a large air pump.
    9. Hi-Visibility Jacket - in case of road side maintenance, we provide you with a Hi-Vis jacket.
  10. The Bike Leader also carries...
    1. BOSCH Nyon GPS | Tool Kit | Basic First Aid Kit
  11. What should I carry with me?
    1. Passport
    2. Insurance Documentation
    3. Cash for the day
    4. Credit/Debit Cards
    5. 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


$2,477 per person

Your adventure includes:

Your adventure includes:

  • 8 Day | 7 Nights
  • Accommodation of Distinction
  • All Breakfasts
  • Bistecca alla Fiorentina Night
  • 5 Cycle Days
  • Family-Run Hotels & Country Houses
  • Private Tours, 2 Wine Tastings
  • Visits to Vignamaggio, Chianti, Siena, San Giminiano & Volterra
  • A More Mature, Full Time Bike Leader
  • Rest Day in Volterra
  • Customised Pedal Assist eBike
  • Small Group - Max 8 Guests
  • On Safari Luggage Transfers & Support Vehicle
  • ☀️FULLY GUIDED Indulgence Accommodation | Guaranteed Quality Accommodation

The Day We Saw Siena - First Test Ride

At Inspired ITALY, we try everything before we let our guests anywhere near the finish product. Here is a short video of our very first test ride [June 2019].

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The people of Tuscany were very pleased to receive us as guests and went above and beyond to make our stay memorable.

Colin Protheroe

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