Cycling in Tuscany

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7 nights
8 days
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Our leisurely cycling tour will meander through this beautiful land of vineyards, olive groves and stunning scenery with medieval villages in the distance shaping the landscape and mesmerising you to another time. This tour combines your cycling passion with an authentic experience of the Tuscany highlights.

Our leisurely cycling in Tuscany tour allows you to experience the Tuscan countryside in a unique way. Cycle through the hills and valley of Cortona, from Cortona to Lago Trasimeno and take the ferry across to Isola Maggiore, stopping for a picnic lunch in the olive groves or a wine tasting at a family run Cantina along the way. During this tour you will also experience the best of our ‘Taste of Tuscany’ tour connecting you with the locals and after a day of cycling, indulging in traditional food and wine!

As a personalised package, this can depart on any Saturday requested subject to availability, with a minimum of two guests.

Highlights & Inclusions

  • Accommodation for 7 nights’ in a Tuscan villa (one accommodation for the duration of the tour) with all modern facilities and a fantastic swimming pool with stunning views of the surrounding countryside.
  • Day tours to itinerary locations
  • Bi-Lingual Hosts for the duration of the tour
  • Bikes & Helmets for Cycling days
  • Ferry tickets for travel to Isola Maggiore
  • Cooking Experience
  • Complimentary bottle of wine and beer
  • Wine tasting at selected vineyards/establishments
  • All breakfasts. 5 lunchs & all dinners (a-la-carte) at a local trattoria or restaurant. Wine included
  • All travel to and from tour locations as detailed on itinerary
  • Transfers to and from the local train station on your arrival and departure days.


Day 1: Arrival

We transfer you from our local train station to your accommodation and allow you to settle in and familiarise yourself with your new surroundings which will be ‘home’ for the next 8 days. Dinner in Cortona.


Today we will spend the morning cycling the stunning countryside and hillside of Medieval Cortona, the setting for the movie and book “Under the Tuscan Sun”. We will stop for lunch at a trattoria in Cortona to indulge in some local dishes. After lunch you will have some free time to explore and get to know this beautiful township; Visit the many boutiques & art galleries. Return to the villa by bike or car mid to late afternoon for a little relaxation by the pool. Dinner in Cortona.


We visit San Gimignano for the morning. This is a beautiful medieval township; a step back in time. This township houses many stores which offer a very broad range of painted ceramics as well as leatherware and alabaster. Two wonderful piazzas where you can simply stroll, visit a museum or climb
a tower for a breathtaking view of the Val d’Elsa or enjoy a delicious gelato. After lunch at a local trattoria we will head back towards Siena.
You will have the afternoon to explore Siena; a visit to the spectacular Piazza del Campo, where the famous bareback horse race is held or Visit Il Duomo, The Mangia Tower or simply stroll the streets and enjoy the ambiance and the various delights Siena offers, from the little food stores with many tempting treats to the beautiful selection of stores/boutiques. Dinner in Cortona.


Spend the day exploring the beautiful Lake Trasimeno by bike. Departing from Cortona we will ride approx. 15 – 20km before arriving at our lunch spot. We will then explore the lake area before taking a ferry across to Isola Maggiore where we will spend a few hours. There will be the option to ride back to Cortona or to be transferred by car. Return to the villa late-afternoon for a short rest prior to travelling to
a nearby property dating back to the 1500’s for a hands-on cooking experience with a local chef, Donatella, who has over 20 years’ experience researching and rediscovering ancient recipes and Tuscan cooking traditions. Savour the dishes you have prepared with the chef including local wine.

Day 5: Wednesday - Cycle Montelpulciano

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.

Day 6: Thursday - CHIANTI

A leisurely day of taking in the most amazing views, whilst driving through this most famous wine growing area of Tuscany. During the morning, we will visit the village of Castellina; we will enjoy a Caffè together after which you will enjoy free time to explore this village which offers a wonderful selection of varied stores. We will then visit a vineyard a short distance away, interact with the winemakers and savour lunch and a wine tasting whilst enjoying spectacular views of the vineyards and olive groves. Return to villa late afternoon. Dinner in Cortona.

Day 7: Friday - Tour free day

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.

Day 8: Saturday - DEPARTURE

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.


Starts Ends Price Status Book
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Single supplement (if required)
City Tax: some City Councils may introduce a tourist tax that has to be paid directly at the hotel
Meals and beverages other than those specified
Everything which is not clearly specified under inclusions

* Please note, price is subject to fluctuation and availability is subject to change until booked and confirmed *