Radda, Tuscan Village - Italy


Italian Classic: The best of Tuscany

Guided 7 days

This seven-day road bike tour through Tuscany will take you through some of the most magical landscapes in Europe, steeped in history and dotted with enchanting villages full of surprises. Discover the real Italy on two wheels.

Road cycling
350 km

Tour overview


The Italian region of Tuscany has perfected the art of hospitality. On this seven-day road bike leisure tour across this spectacular region, enjoy a combination of excellent accommodation and acclaimed restaurants, carefully and personally selected by those specialised in local cuisine.

Our aim for this cycling holiday, as well as for the other tours we organise, is not just to help you discover new and fascinating locations while riding your road bike, but also to ensure you enjoy the very best this area has to offer, including bike routes, scenery and local culture.

This Tuscan road bike tour will guide you through two regions of Italy in 6 days. Each day you’ll ride between 60 and 80 km, meaning the tour is suitable for intermediate cyclists with experience on a road bike. You will be accompanied by our guide riding alongside the group the whole time, as well as our minibus providing support should any unforeseen issues arise.

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

Flights not included. Direct flights available at lastminute.com

Highlights of your cycling trip

Tuscan cuisine - food

Incredible Cuisine

Sample some of the most delicious Italian cuisine, which, if it’s possible, will taste even better after a long day in the saddle. Many of our routes also take us through world-famous wine regions where we’ll get the chance to taste some of Italy’s best wines.

Tuscany hills sunrise - tuscany, Itlay

Magical Landscapes

Italy is home to some of the most beautiful landscapes in the world, from soaring mountain peaks to vast green vineyards that stretch as far as the eye can see, as well as stunning coastlines that invite you to sit back, relax and soak up the sunshine.

Daily Luggage Transfers

Each day, the team will transfer your luggage from hotel to hotel, meaning all you have to do is focus on cycling. We encourage you to bring your own personal essentials and favourites along with you on the bike, such as energy gels and bars, but the rest of your belongings will be in safe hands.

Tour destination

Tuscany - Italy

Tuscany is at the top of many road cyclists’ bucket list. It is a dream riding location given its long empty roads that sweep across undulating countryside, and some of the Strade Bianche routes come along these very roads. It is home to world famous cities such as Florence and Pisa, as well as countless romantic Renaissance villages, perched atop the hills and mountains overlooking the vast green countryside below. We’ve planned this tour in order to show you the best of the best of Tuscany, as we ride through some of the most beautiful and memorable landscapes in the country.

  • Weather

    Italy has a wonderfully pleasant climate with mild sunny winters and hot steamy summers. It is a fantastic year-round location for cycling, especially during the off season, when you can enjoy quieter roads and cycle all day long without having to avoid the midday heat.

  • Terrain

    From undulating green fields of vineyards to soaring mountains and glistening coastline, this area of central Italy really has it all. It is home to some tough climbs and beautiful descents, but also flatter landscapes and sweeping roads that make for a much calmer riding experience. Hot summer days can get quite dusty, so make sure to pack your glasses and a face covering in case you find yourself in the middle of the peloton!

  • Culture

    Italian culture and people are known around the world for being warm, welcoming and friendly. Not only will we get to see some incredible sites and meet some wonderfully kind people, we will also get to taste some of Italy’s best food and wines, grown and produced in the very regions we’ll be riding through. This tour really is an all-round Italian experience and adventure, certainly one that will leave you wanting to extend your stay!

Accommodation during your tour

Comfortable 2* and 3* Accommodation

You will sleep in a range of two- and three-star hotels along our route, all of which offer a very pleasant stay after a full day of riding. We chose the accommodation based on its location and proximity to the routes we have chosen to ride. Each location includes secure bike storage facilities and other amenities aimed at cyclists so you can focus on some well-deserved R&R.

Sangallo Park Hotel, 3*

Breathtaking views of Siena

The Sangallo Park Hotel awaits you on the panoramic hill of Vico Alto in the northern part of Siena. The hotel is less than 3 km from the historic centre and is close to the train station, Policlinico Le Scotte hospital and the University of Siena.

Hotel dei Capitani, 3*

Located in the heart of charming Montalcino

Situated in the historical centre of Montalcino, this 18th-century building is set in the magnificent Tuscan countryside, between the valleys of Arbia and Orcia. The hotel has a large garden with a swimming pool, built in a style consistent with its Mediaeval surroundings, and the rooms also retain the flavour of their ancient Tuscan setting.

Sant Apollinare Farmhouse

A family-run guest house nestled in the Tuscan hills

The charming Sant Apollinare Farmhouse is located in the Sienese, Val d’Orcia (UNESCO World Heritage Site). It has been passed down from one generation to the next for over 70 years. The main building is a renovated and tastefully decorated farmhouse, where peace, tranquillity and hospitality reign. The extensive grounds offer plenty of space to relax after a full day of riding,

Tour itinerary

Your guide to a perfect cycling tour

Siena and Chianti Loop
  • Distance
    70 km

To kick off our tour, we’ll be riding through the extraordinary Chianti Hills area, famous around the world for the excellent Chianti wine grown on the land. We’ll set out directly from the hotel in Siena and head to Gaiole in Chianti. We’ll ride across the rolling hills surrounded by vineyards, deep in the enchanting landscape. Our next stop will be Radda in Chianti, where we’ll stop for a coffee and ice cream in the magnificent old square. Just a few kilometres left before heading back to the hotel where we can relax in the swimming pool and get freshed up ready for our delicious dinner in Siena. We will spend the night once again at Sangallo Park Hotel.

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: Siena Airport

When best to arrive: Day 1 of the tour

Where the tour starts: Siena

Transfers: Transfers from Siena train station to the hotel are included in the price of this tour.

Flying out

Fly out airport options: Siena Airport

When best to depart: In the afternoon on Day 7 of the tour

Where the tour ends: Siena

Transfers: Transfers to Siena train station from the hotel are included in the price of this tour.

Tour essentials

What’s included in your cycling trip.

  • Sangallo Park Hotel - Tuscany / Italy
    Comfortable Accommodation

    6 nights in 2 & 3* hotels in a shared room with en-suite facilities. Single rooms are available as an additional extra.

  • Tuscan cuisine - food

    All breakfasts and dinners are included on this tour so you can be assured that you will be adequately fuelled for every day of riding.

  • Support vehicle
    Luggage Transfers

    Your luggage will be transferred from hotel to hotel throughout the trip so you only need to pack a day bag for your essentials.

  • Guide Photo
    Guide and Support

    Throughout the tour you will have experienced guides riding with you as well as have a mechanic on standby for any necessary work needed.

Cycling bottle

What’s not included in your cycling trip.

  • Flights

    Flights are not included in the tour package. We have suggested which flights and airports are best suited for this tour but should you have any doubts or questions, please do not hesitate to reach out to us.

  • Health & Travel Insurance

    We strongly recommend that you obtain a dedicated health insurance that covers your sports activities. Reach out to us if you have questions about the insurance.

Bike Rental
Make your travel arrangements just that little bit easier!

It’s not always easy travelling with a bike but fear not, quality carbon 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. 

Giant TCR Advanced 2
Giant TCR Advanced 2

Fitted to you and ready to ride!

E-Bike Rental
A little help to make your tour that much more enjoyable!

If you need a bit of a boost or would like to take on the tour at a bit more of a leisurely effort, then why not rent an e-bike for your tour?

Using an e-bike opens you up to new possibilities and can allow you to take on even more than you imagined. Also, if you are part of a group of varying abilities or you are coming back from a recent injury, an e-bike will allow you to enjoy the tour on the same level as everyone else. 

If you would like to rent an e-bike for your tour, please select this option at checkout.

endurace-on EBIKE
Brands and models may vary

Fitted to you and ready to ride!

More things to maximise your cycling trip

  • Additional Nights

    The tour starts in the morning and ends in the evening, plus airport transfers take time. We recommend that you fly in the day before and fly out the day after to maximise your trip and avoid unnecessary rushing. You can book these two additional nights when you proceed to the booking process. Please contact us to arrange this and inform us if there is anything specific you may require.

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
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Booking options