The Day I Saw Siena

8 Days | 7 Nights | Fully Guided

The Day I Saw Siena

Fully Guided Ride through Siena, Chianti & San Gimignano

Tuscan Art, Architecture, Food, Wine & History

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


☀️ This is Tuscan Cycling to be Enjoyed, Not Endured ☀️


Prices from $3,296 per person View Prices


  • 8 Days | 7 Nights
  • All Breakfasts
  • 🥩 Famous Fiorentina Steak Night
  • 💁🏼 A More Mature, Full Time Bike Leader
  • 🍷 Chianti Wine Tastings & Lots of Wine Opportunities
  • 🥂 Welcome Drinks | Sun Downers in San Gimignano
  • 🐛 Siena Caterpillar Contrada Private Visit & Tour
  • 🏰 Stay in 2 Tuscan Castles
  • Small Groups | Max 8 Guests
  • Outstanding Scenery | History | Art | Food | Wine
  • Visits | Tours | Anecdotes
  • Luggage Transfers
  • ☀️ FULLY GUIDED INDULGENCE Itinerary | Guarantee of Quality Accommodation


  • ACTIVITY LEVEL: EASY with short 'Moderate' sections
  • CYCLING PER DAY: 1h to 2hrs
  • 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 (Florence) soon has you in the bosom of Chianti. You can, on occasion and at the right time of year, detect just the hint 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: Mona Lisa & Chianti

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 and the taste of Chianti Classico wine!!

In the evening, we join Dario Cecchini for his famous Bistecca alla Fiorentina dinner.


⭐️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 in 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.

The short downhill ride to Castello di Tornano where we are welcomed for a single night stopover and a wine tasting in the dungeon!


⭐️ Radda in Chianti ⭐️ Lecchi in Chianti ⭐️ Lunch


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: The Day You See Siena

Today we conquer Siena! We ride to its very heart to meet Dario Castagno in the sacred centre of Siena's Caterpillar Contrada, which last won the Palio in 2003, for an extraordinary tour and history lesson.

We visit the Piazza del Campo famed venue of the Palio.

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

An evening pre-dinner walk along the walls of Monteriggioni is a must.


⭐️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 Gimignano

After breakfast, we slip away through the ancient gate of Monteriggioni into the country roads and throw a look back at your overnight location. Truly extraordinary!

A steady ride to San Gimignano 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.

I hope that we can tempt you away from your panorama bedroom for a Sundowner Spritz!


⭐️Wheat fields of Tuscany ⭐️San Gimignano


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


Hotel la Cisterna | San Gimignano ✩✩✩

"..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 Gimignano to Volterra is a great favourite.

Vast expansive vistas, the enormous freewheeling descent and even the climb to Volterra are such stimulating experiences.

We stop to have lunch just before the climb to Volterra. This quiet unassuming town has plenty of 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

Take 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 enjoy a local lunch and wine tasting!

The hotel pool is very inviting too!

We will find time for a relaxed wine tasting today.

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 your next location ... Pisa, Firenze or Rome!


Ciao, baci e abbracci!

Journey Map

FAQ's - The Day I Saw Siena

“... 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 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. Our oldest guest is Geoffrey who was 84 years of age at the time of his Safari. The youngest was 12 years.
  2. How busy are the roads? Italian roads tend to be much quieter than people are used to and the Italian drivers are much more considerate to cyclists than most other nations. The vast majority of your itinerary is along quiet country roads. The exception is cycling through Siena.
  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 a 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


$3,296 per person

Your adventure includes:

Your adventure includes:

  • 8 Day | 7 Nights
  • 💁🏼 Fully Guided 24/7 with A More Mature Bike Leader
  • 🍽 MEALS: All Breakfasts
  • 🥩 Bistecca alla Fiorentina Dinner with Dario Cecchini
  • 🥂 Welcome Drinks | Sundowner Spritz in San Gimignano
  • 🍷 WINE TASTINGS: Vignamaggio Wine Tasting | Castello di Tornano | Volterra
  • 🏰 Evening Walk on the Walls of Monteriggioni | Rest Day in Volterra
  • 🏰 Stay in Two Tuscan Castles
  • 🐛 Visit Siena Contrada of the Caterpillar Tour & History with 'Too Much Tuscan Sun' author Dario Castagno
  • Visits to Villa Vignamaggio, Chianti, Siena, San Gimignano & Volterra
  • 5 Cycle Days
  • Customised Raleigh Motus Grand Tour electric Bike with Bosch Pedal Assist
  • Small Group - Max 8 Guests
  • On Safari Luggage Transfers & Support Vehicle
  • ☀️FULLY GUIDED Indulgence Accommodation | Guaranteed Quality Accommodation
  • EXCLUDES: Flights & Transfers - we provide full pre & post trip support & advice on airports & transfers

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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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