Rider on Tuscan road - Italy

Tuscany - Italy

Epic Tuscany: Self Guided Cycling Tour

Self-Guided 7 days

Prepare your legs and your heart for an unforgettable journey! From the vineyards of Brunello d Montalcino to the farmhouses surrounded by olive groves. Grab your bike and discover the Best of Tuscany by bike.

Road cycling
7490 m
412 km

Tour overview


Set out on a bike ride through pure Italian beauty! This unforgettable bike tour takes you through the heart of Tuscany, past superfine red wines, olive groves, and hills shaped by cypresses, as well as wonderful historic centres and cheerful locals.

On the bike, you’ll have a lot of fun. From the winding ups and downs of rolling hills to the enthralling passages beneath mediaeval town walls. Pedal through Brunello d Montalcino and Nobile di Montepulciano vineyards and past farmhouses surrounded by olive groves. Explore the museum cities of Florence and Siena, as well as the legendary Eroica. Prepare your legs and heart for an unforgettable adventure!

This self-guided tour includes GPS tracks and detailed maps of all routes so you can travel at your own pace. Our support van transports all of your luggage from hotel to hotel. If you have any problems, the helpful team will be there to help.

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

Flights not included. Direct flights available at lastminute.com

Highlights of your cycling trip

Rolling Landscapes

The landscape of Tuscany is dreamy and enticing for any road cyclist. These winding roads beg to be ridden, surrounded by some of Italy's most beautiful scenery. Believe us when we say you will fall in love with Italy here.

Dei Capitani Hotel - Tuscany, Italy

Charming Accomodation

Each hotel has been carefully chosen for its idyllic setting. Throughout your journey, you'll feel well rested after each day in the saddle. Every hotel is of high quality, with fantastic facilities that will make your trip even more memorable.

cyclist in the Tuscan countryside - Italy

Self Guided

Pedal at your own pace, following the maps and tracks provided during the pre-tour briefing. We'll recommend places to stop for lunch and sightseeing along the way. If technical assistance is required, it will be provided throughout the event.

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

Il Molinello Agriturismo

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

Throughout the week you’ll be staying in beautiful four-star hotels. Each one has been specifically selected to make sure you are able to rest and relax after a full day of exploring. They also have all the facilities you will need as travelling cyclists.

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 fancy local experience, this is definitely the place!

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

Dei Capitani Hotel

4* Hotel, Montalcino
Via Lapini 6, 53024 Montalcino, Italy

In this ancient building, you can breathe the typical atmosphere of a traditional Tuscan village. The property offers a large garden with a beautiful infinity swimming pool overlooking the valley of the vineyards where the fine Brunello is produced.

You can enjoy a relaxing afternoon on the sun terrace, with large sun chairs and tables overlooking the magnificent Tuscan valley panorama after a long day in the saddle.

Tour itinerary

Your guide to a perfect cycling tour

Asciano to Montalcino
  • Distance
    90 km
  • Climb
    1800 m

In the land of Nobile di Montepulciano and Brunello di Montalcino wines. Today we ride through the Val d’Orcia, a traditional Tuscan landscape of rolling hills dotted with cypress trees that is a UNESCO World Heritage Site. After marvelling at Montepulciano and Pienza, a true Renaissance city, we’ll arrive in Montalcino, the kingdom of the fine Brunello di Montalcino wine.

Overnight stay: Montalcino

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.

  • Breakfast and Accommodation

    As standard, you will be allocated a double room with one other person with ensuite facilities. Breakfast is included in the tour.

  • GPS Tracks Access

    Access to the daily routes through the RIDE WITH GPS mobile application.

  • Transfers

    Transfers in and out from Florence Airport are included.

  • Daily Luggage Transfer

    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.

  • Guarantee a spot during busy periods
  • Only 30% down payment to secure your place
  • Fair & Transparent Cancellation Policy
Booking options