Cycling in Tuscany

Cycling in Tuscany

7 Days

If the idea of traversing the stunning terrain in and around Tuscany appeals to you – then our Cycling in Tuscany tour could be the perfect adventure. There won’t be any racing here; in fact, our leisurely tours have become a firm favourite amongst those looking for a unique way to see the sights and sounds of Lake Trasimeno, Cortona and all surrounding areas.

With options to hire an eBike, travel at your own pace and take in as much of the Tuscan lifestyle as possible; we’re sure that your trip will be as memorable as it is refreshing.

From the hills and valleys, right through to the town centres and the cycle paths – your dedicated tours will take you to the local landmarks and hotspots, while your leisure time could allow you to explore the region at a pace that suits you.

You could take the ferry across to the nearby Isola Maggiore, stop for a picnic in one of the huge, locally maintained fields, or stop in at a wine grove or family-owned cantina that has welcomed locals and visitors alike for years.

There are simply so many opportunities to enjoy that we couldn’t possibly hope to list them all here, but that’s where this tour can come in handy. You’ll see captivating sights, enjoy a cooking lesson in Chianti, partake of authentic food from local suppliers, and witness medieval towns first-hand.

To be eligible for this tour you’ll need to book with 2 people at the minimum; making this option one of our most popular for couples looking to share the romantic backdrop of Tuscany together, or small groups of cycling enthusiasts keen to tackle an entirely unique type of adventure.

Departure Days
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Tour Itinerary

7 Days - Cycling in Tuscany

Your Tuscan cycling adventure is about to begin. To ensure that you arrive at your villa safely, we’ll collect and transport you from the local station to our world-class villa. You’ll be given a full afternoon to explore your local environment; with options to tour our traditional farmhouse villa, the pool area and our immediate surroundings. Once you’re settled in and are ready to start your trip, we’ll take you into the local town of Cortona for dinner, where you’ll enjoy a Tuscan-style dinner.

We’ll collect you from your accommodation and then embark on the next stage of your journey – travelling into Cortona and the surrounding countryside. The first part of your cycling tour will commence, with an adventurous exploration of the local scenery, across cycle paths and in a way that will allow you to take in all of the veiws. We’re sure that you’ll have worked up an appetite and at 1pm, we’ll head back into town to enjoy a spot of lunch. You’ll then have the opportunity to enjoy a little free time, which you can use to shop, cycle around the area, or relax by one of the captivating landmarks in the region. With your bike and safety gear still available, you will enjoy a leisurely bike ride back to the villa. After a few hours of relaxation time in the pool, interacting with your fellow tour-guests, or taking a pleasant walk or bike ride locally; we’ll take you into Cortona for a lovely dinner
Cycle Countryside & Township

“San Gimignano is a town so iconic that you have to see it to truly believe it – and this is where we’ll be headed at 9am. Upon arrival we’ll have a brief coffee break and you will be given an overview of the town and its rich history. Shortly after your introduction, you’ll have free time to explore, ingratiate yourself with the locals and partake in activities at your own leisure. We’ll then travel to Siena, where you’ll meet your tour guide who will fill you with knowledge, expose you to the traditional lifestyle and allow you to get to grips with the town first-hand.
To allow you to take in as much as possible, you’ll have a little more free time before your evening meal.
For dinner, you’ll be taken to one of the local restaurants in Siena, where you’ll get to taste the mesmerising flavours that the region.”

Your tour of Lake Trasimeno will begin with you being picked up and transported ready for the adventure ahead. You’re more than welcome to purchase and prepare your own lunches and can eat at your leisure. The lake makes for a fantastic backdrop for cyclists as well. At 3pm, we’ll transport you to the next destination; a fully equipped kitchen where you’ll learn to prepare your own 4 course Italian meal. Guided by a world-class Italian chef, your Traditional Tuscan Cooking Lesson will take place and you’ll get to enjoy the fruits of your labour with the chef once you’re finished cooking Class.

A full day of exciting cycling activities are on the agenda today. We’ll begin by picking you up and transporting you to your destination. First of all, you’ll be able to take to two wheels with a full cycling tour of the stunning region of Montepulciano. This tour will be followed by lunch and you’ll get to partake of the locally sourced ingredients that go into the meal. After, you’ll have free time to explore the area. As there is simply so much iconic scenery and so many stunning views in Montepulciano, we’re sure that you’ll feel spoilt for choice. You will then have the option of cycling back to the villa for 3pm. If you’d prefer a ride, we can transport you instead. With a few hours to spend on leisure time, you’ll be able to look forward to a fine dining experience at a local restaurant in Cortona; which we will take you to and from.

This morning we have an exciting tour of Chianti on the cards. We’ll be stopping in Castellina for a coffee and the exhilirating opportunity to explore the town and all it has to offer. We then have an extended lunch and tasting session planed at an exquisite organic winery, where there will be the opportunity to meet the winemakers.

As your trip slowly comes to an end, we allocate this time for you to choose the types of activities that you’d like to partake in – from exploring the nearby area, to relaxing by the pool. Whatever you choose to do, we’ll ensure that you’re back in time for a traditional Italian Aperitivo, followed by a farewell dinner to mark your visit.

In the morning, we’ll take you back to the local station where you can commence your return journey with plenty of Tuscan memories to savour for a lifetime.

What is Included

7 Days - Cycling in Tuscany


  • A full 7 night villa stay in the heart of Tuscany
  • Our bilingual hosts & tour leaders will be on hand throughout the tour to assist you
  • Scheduled tours as mentioned in the itinerary
  • Full breakfasts supplied along with apartment provisions
  • 3 enjoyable lunches at local eateries or during tours
  • 6 restaurant or trattoria dinners including traditional Italian wine
  • Full bike tours with a guide and helmets – and options for eBike bookings
  • Walking tours across Cortona and Siena to immerse you in the Tuscan lifestyle
  • An enjoyable cooking lesson where you’ll get to eat your 4 course meal with the chef
  • A complementary bottle of wine and beer will be provided with all bookings
  • A world-class wine tasting experience at a local establishment
  • Your travel will be catered for, both to and from itinerary locations
  • All tour free days include transport to local stations if needed
  • Free transportation to and from stations when you arrive and depart from your tour
  • Optional transport into the town of Cortona on a tour free day


  • For up to date airfare prices, it’s a good idea to get in touch with a carrier near you – you’ll be responsible for these costs
  • Although not an obligation in Italy, traveller’s insurance is recommended. You might want to compare prices for this
  • Many museums and galleries in Tuscany and the local towns charge a fee for entry
  • Any meals outside of those mentioned within your itinerary will be your responsibility to cover
  • Personal expenditure such as shopping, outside-of-tour hire and other such expenses will need to be paid for by you

Il Mandorlo, Fratticciola

Il Mandorlo is a rural house dating back to the 17th Century which has been restored in keeping with its original shape and materials. It is located in the valley ‘Val di Chiana’ nearby the historical centre of Cortona.

The house is divided into five apartments with all modern facilities including air conditioning and WI-FI. The grounds are beautifully maintained and the infinity swimming pool provides a panoramic view of the historical centre of Cortona and surrounding valley.

Set in a quiet location but close enough to the main roads which connect to all the well-known historical cities and villages.

It is an image of rolling hills, vineyards, age-old trees, golden wheat in Spring, Sunflowers in Summer and the constantly changing shades of the earth.

Accommodation is subject to availability at time of booking.

Getting there

7 Days - Cycling in Tuscany

The tour begins near the historical centre of Cortona. Upon arrival we will meet you at our local train station Camucia-Cortona and will transfer you, via vehicle to the villa, which is a short drive into the countryside.

Cortona is located 2.5 hours by regional train from the main train station in Rome (Roma Termini) and 1.5 hours by regional train from the main train station in Florence (Santa Maria Novella).

Train Travel to the Villa

If you are already in Italy connection to either Roma Termini or Firenze Santa Maria Novella train stations is easily accessible via other train stations.

Either of these two major cities are a good option for your arrival into Italy and then travel to our location. We will meet you at our local train station Camucia-Cortona and will transfer you, via vehicle to the villa, which is a short drive into the countryside.

Arrival from Rome Airport:

  1. Take the Leonardo Express Train from Rome Airport to Roma Termini Train Station (This is a 30min journey and will cost approximately 15 Euro)
  2. From there take a regional train to Camucia-Cortona (This is a 2.5hr journey and will cost approximately 15 Euro)

Arrival from Florence Airport:

  1. Take the bus that goes to Firenze Santa Maria Novella Train Station (This takes approximately 30mins and will cost approximately 15 Euro)
  2. From there take a regional train to Camucia-Cortona (This is a 1.5hr journey and will cost approximately 13 Euro)


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7 Days – Cycling in Tuscany

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