Sunset in Asciano Tuscany - Italy

Tuscany - Italy

Classic Tuscany: Italy Essence Cycling Tour

Self-Guided 8 days

Immerse yourself in the purest beauty. This memorable bike holiday takes you to the heart of Tuscany, among superfine red wines, olive groves, and hills designed by cypresses. Simply breathtaking.

Road cycling
5488 m
302 km

Tour overview


Immerse yourself in the purest beauty of Italy. This memorable road bike holiday takes you to the heart of Tuscany, among superfine red wines, olive groves, and hills designed by cypresses, wonderful historic centres, and cheerful locals.

You will ride from the Crete Senesi to the lands of the Vino Nobile di Montepulciano and Brunello di Montalcino, passing the “ideal city” of Pienza. Then the medieval atmosphere of Siena and San Gimignano will welcome you. And finally, the Chianti Classico and the romantic routes of the Eroica will close your wonderful journey.

This self-guided tour includes GPS tracks and detailed maps on all the routes for you to follow the itinerary at your own pace. All your luggage is transported from hotel to hotel by our support van. If you run into any issues, the helpful team will be there to assist.

Start point
End point
See program for full itinerary
Flying in
Flying out

Flights not included. Direct flights available at

Highlights of your cycling trip

Rider on Tuscan road - Italy

Rolling Landscapes

Tuscany's landscape is dreamy and alluring for every road cyclist. These rolling roads beg to be ridden, surrounded by some of Italy's best countryside. Trust us when we say you will definitely fall in love with Italy here.

Charming Accommodation

Each hotel is carefully selected in dreamy locations. You'll feel well rested after each day in the saddle throughout your trip. Every hotel is of a high standard with fantastic facilities to make the trip even more memorable.

cyclist in the Tuscan countryside - Italy

Self Guided

Pedal at your pace following the maps and tracks provided during the pre-tour briefing at your arrival. We'll advise you where to stop for lunch and sightseeing along the way. Technical assistance will be available throughout if needed.

Tour destination


Dusty roads and rolling countryside – Tuscany is a dream to ride. Road cyclists should be adding this Italian gem to their hit list. After all, if it's good enough for the pro's then it's good enough for us! Pedal the same routes that are used in the Strade Bianche and discover why we're mad about Tuscany.

Discover More
  • Weather

    Boasting warm and mild weather all year round, Tuscany really is a dreamy destination. The height of summer can get too hot for some in the midday sun. So if you prefer slightly cooler temperatures, perhaps book for spring or autumn dates for a more comfortable ride.

  • Terrain

    Dusty, hilly, and rolling. The roads run beautifully through Italy's interior with tough climbs and fun descents to tackle. Hot summer days really do kick up the dust. Don't forget your glasses and a face covering if you are normally at the back of the peloton!

  • Culture

    Warm and welcoming. Italian hospitality is famous across the globe. Be prepared to be blown away by hearty food and rich flavours, incredible wines, and the all important family feeling that runs throughout the region. Tuscany will leave an imprint on you after your visit.

Accommodation during your tour

Luxury Il Molinello Agriturismo

4* Hotel, Asciano
Localita Molinello 148, 53041, Asciano Italy

Il Molinello is a cosy accommodation in the rolling hills east of Siena, better known as the Crete Senesi. Alessandro and Elisa produce high-quality extra virgin olive oil. If you want a super local experience, this is definitely the place!

This family-run farm is the perfect place to start your Classic Tuscany tour.

Luxury Hotel Corsignano

4* Hotel, Pienza
Via della Madonnina 11, 53026, Pienza Italy

Beautiful, functional and, above all, ecological. This is our comfortable 4-star hotel, set in the frame of Tuscany’s most beautiful and unspoilt area, reaching from Pienza to the Orcia-Valley, passing along the colourful roads you have always dreamed of.

Another beautiful stop along the journey of this Classic Tuscany tour.

Tour itinerary

Your guide to a perfect cycling tour

Asciano to Pienza
  • Distance
    50 km
  • Climb
    1098 m

Across the beautiful villages of Montepulciano and Pienza

Today we ride through the Val d’Orcia, a quintessential Tuscan landscape, made out of rolling hills dotted with cypress trees; its landscape is listed as a UNESCO World Heritage Site. After the marvellous Montepulciano, we end in the pretty Pienza, a real model of Renaissance city.

Overnight: Pienza
Included: Breakfast

Getting there

Information to help you book your flights and get around.

Any questions about flights and transfers? The Epico team is here for you. Ping us via the chatbot in the corner of your page or send an email to [email protected]

Flying in

Fly in airport options: Florence

When best to arrive: in the morning the day the tour starts

Where the tour starts: we meet in the afternoon in Asciano

Transfers: included from Florence

Flying out

Fly out airport options: Florence

When best to depart: in the evening of the day the tour ends after 17:00

Where the tour ends: in the afternoon in the town of Asciano

Transfers: included to Florence

Tour essentials

What’s included in your cycling trip.

  • Luxury Accommodation

    7 nights in 4* hotels in a shared room with en-suite facilities. Single rooms are available as an additional extra.

  • GPS Routes

    Access to tracks of the route through the RIDE WITH GPS mobile application

  • Support vehicle
    Airport Transfers

    Transfer to and from Florence Airport is included

  • Daily Luggage Transfers

    Support vehicles will transport your luggage on to the next hotel, so you only have to carry your essentials

Cycling bottle

What’s not included in your cycling trip.

  • Flight

    Flights are not included in the tour package. Please follow our advice about which flights will be best suited for this tour. Reach out to us if you have any questions about flights.

  • Travel Insurance

    Travel insurance is essential and we always recommend you carry out your own insurance search for your specific needs.

Bike rental
Only €220 for the entire trip

It’s not always easy travelling with a bike but fear not, road bikes are available for rental for the duration of the tour. To make sure you get the maximum from your bike for your trip, we’ve partnered with some of the best brands in cycling to give you the latest choice of equipment.

With a variety of sizes available, we can ensure your bike fits you perfectly.  All rental bikes are mechanically checked and adjusted before each and every hire so you can have peace of mind that your bike will be running smoothly from start to finish!

You can select this option when you proceed to checkout. 

Brands and models may vary

Fitted to you and ready to ride!

More things to maximise your cycling trip

    Single accommodation
    €252 per person for entire trip

    If you’d like a whole room to yourself, that’s no problem. For an extra €252 for the trip duration, you can enjoy the comfort of your own room. Just select this option when you proceed to book your tour.

Booking options

Choose when you want to travel

Don't see the travel dates you want or have a special request, such as adding a non-rider, please contact us.

  • This tour has flexible dates. We can make it start and finish the day you need. Contact us to request alternative tour dates!
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Booking options