Italy 08:38 – 28 November 2020

Cycling through Siena

NEW for 2020 | GPS Self Guided 8 Day 7 Nights

Ride through the Tuscan Treasures of Chianti, Siena & San Gimignano

Vast Vistas & Long Weaving Descents through Tuscan Countryside

A GPS Self Guided eBike ride through true Tuscan treasures and countryside. The towns and villages of Chianti, the UNESCO World Heritage sites of San Gimignano and Siena with the surprise of Monteriggioni & Volterra combine to provide a sketch pad of life long memories. Page upon page of meals, vistas and long, weaving descents all set under the expanse of Tuscany skies.



☀️ Cycling to Enjoy, Not Endure ☀️

Prices from $1,763 per person View Prices


  • 8 Days | 7 Nights [ 5 night itinerary available ]
  • Bed & Breakfast with Half Board Option
  • Chianti | Siena | San Gimignano | Volterra
  • Stay in the Heart of the Chianti Wines Region
  • Visit the Piazza del Campo Siena
  • Stay in a Tuscan Castle
  • A Night in San Gimignano
  • Vast Vistas of Volterra
  • All Luggage Transfers Included
  • Turn-by-Turn GPS Navigation
  • Full Support & 24h WhatsApp Virtual Guide
  • ✤ 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


This is the bosom of Chianti.

Famed for its wonderful wine and a stones throw from where Monna Lisa once lived and, it is said, Leonardo Davinci visited.




Hotel Sangiovese | Panzano in Chianti ✩✩✩

"..a very quiet, charming little village. We stayed only 1 night but wish it had been a week.

Find out more:
Travellers Tales article

Day 2: Villa Vignamaggio and Greve in Chianti

Greve in Chianti is the principal town of the Chianti region and an easy, short ride from your hotel.

Every year in the unusual piazza hosts to the Chianti Classico Expo and wine festival, usually every September. CLICK HERE

The valley is dotted with history and acre upon acre of Chianti Classico vines including at the Villa Vignamaggio estate.


⭐️Greve in Chianti


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


Hotel Sangiovese | Panzano in Chianti ✩✩✩

"Very kind and helpful staff (especially guy called Fabio). Clean, nice, simple rooms.

Find out more:
Travellers Tales article

Day 3: Serendipitous Chianti

From Panzano to Radda in Chianti is an easy ride along quiet roads.

Arrive in time for lunch in one of the many restaurants.

After lunch, drop into the valley and the side roads of Chianti towards Lecchi in Chianti and the short ride to Castello di Tornano, a castle lost amongst vines, olives and oak forests of Chianti.

Truly a dream location and your overnight accommodation.


⭐️Radda in Chianti ⭐️Lecchi in Chianti ⭐️Chianti Views


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


Castello di Tornano | Gaiole in Chianti ✩✩✩

"a peaceful place to stay, where olive oil and wine are produced. The people here are wonderful! They go above and beyond to make this experience personal and excellent!"

Find out more:
Travellers Tales article

Day 4: Siena

Siena awaits and your arrival is surprising!

The GPS navigates you through lefts, rights and forks in the road, there it is, the Piazza del Campo, the most famous of Italian piazzas.

Leaving Siena behind and a return to the Tuscan countryside, this time it is the turn of Monteriggioni to take you unawares!

What is this extraordinary place?


⭐️Siena ⭐️Piazza del Campo ⭐️Monteriggioni


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


Hotel Il Piccolo Castello | Monteriggioni ✩✩✩✩

"Excellent place. So delighted with it!! Service is amazing, really kind and attentive staff. Restaurant quality is great. Everything is very well taken care of. We sat by the swimming pool, relaxing while sipping a cocktail ...

Find out more:
Travellers Tales article

Day 5: San Giminiano

After a few minutes in the saddle, throw a look back over your shoulder. Monteriggioni looks truly extraordinary!

The ride to San Gimignano through wheat fields is steady, quiet and easy.

Then cycle to the very centre of this wonderful UNESCO town and stay a night.


⭐️ Wheat fields of Tuscany ⭐️San Gimignano


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


Hotel la Cisterna | San Gimignano ✩✩✩

"Amazingly located in heart of San Gimignano... Cute & cozy little room with spectacular view. Special big plus point for yummy breakfast with view ....

Find out more:
Travellers Tales article

Day 6: Vast Vistas & Long Weaving Descents

From San Giminiano to Volterra provides such memorable views. Looking back at the San Gimignano skyline and onwards with the rolling terrain and staggering views just before Volterra.

The seemingly never-ending freewheel descent before Volterra feels like a cheat and so exhilarating.

Volterra is a quiet, unassuming town with many surprises.


⭐️Views of San Gimignano ⭐️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

The history of this extraordinary town rolls back over 28 centuries. Imagine!

The ancient Roman theatre which is incredibly intact was built around 900 years after the town was founded!

Take some time to saunter through the alleys ways, streets and undercrofts, maybe stop for a wine tasting and definitely take lunch here.

The hotel pool is very inviting too!

OPTIONAL: Take a Short Ride Loop Ride


⭐️Views of Volterra


Rest Day


Hotel San Lino | Volterra ✩✩✩✩

"Excellent this little treasure in the heart of Volterra that gives you elegance, relaxation and an excellent breakfast ... very comfortable beds !!

Find out more:
Travellers Tales article

Day 8: Departure

Head off to your next location ... Pisa, Firenze or Rome.


Ciao, baci e abbracci! 

Journey Map

FAQ's - Seven Tuscan Nights & 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 Cycling through Siena eBike adventure requires around 2 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 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 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?
    1. Water Bottle & Holder - Each bike is equipped with a handlebar 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 roadside emergencies. Each hotel keeps a large air pump.
    9. Hi-Visibility Jacket - in case of roadside 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


$1,763 per person

Your adventure includes:

Your adventure includes:

  • 8 Days | 7 Nights [ 5 night itinerary available ]
  • Bed & Breakfast | Half Board Option
  • 5 Cycle Days
  • START: Panzano in Chianti | FINISH: Volterra
  • Chianti | Siena | Monteriggioni | San Gimignano | Volterra
  • Smaller, Family-Run Hotels & Country Houses, providing an authentic experience
  • Rest Day in Volterra
  • Customised Pedal Assist eBike
  • On Tour Luggage Transfers & Support Vehicle
  • ✤ INDULGENCE Itinerary | Guarantee of Quality Accommodation | See Itinerary for full details | Villas - Castles ✤

Cycling through Siena - First Test Ride

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

More eBike Adventures

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

Colin Protheroe

Our Umbria e-Bike Safari

Niccone Valley | Montone | Gubbio | AssisiUMBRIA | Guided
  • • 7 or 5 Nights
  • • Indulgence Guided
  • • Average hours of activity: 2h 52m
  • • Prices from $2,287 per person

Terroir of Tuscany

Cortona | Val d'Orica | Montalcino | Crete Sienesi | Chianti TUSCANY | Guided
  • • 7 Nights
  • • Indulgence Guided
  • • ⭐️ Sunday Times Best Cycling Breaks
  • • Average hours of activity: 2h 41m
  • • Prices from $3,580 per person

Indulge in Umbria

Cycling to be Enjoyed, not enduredUMBRIA | GPS | Self Guided
  • • 7 or 5 Nights
  • • Indulgence Accommodation
  • • Easy Paced Umbria eBike Tour
  • • Average hours of activity: 2h 50m
  • • Prices from $1,863 per person

The Translation of Sunshine

GPS Self Guided Cycle Touring through TuscanyTUSCANY | GPS | Self Guided
  • • 7 or 5 Nights
  • • Classic Accommodation
  • • Tuscany family bike tours
  • • Average hours of activity: 1h 46m
  • • Prices from $1,299 per person