Australia (+61) 400 191 511

Italy (+39) 331 4253965


Cycling Tour

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. Stopping for a picnic lunch or lunch at a local trattoria will energise the body for your onward journey. This tour combines your cycling passion with an authentic experience of the Tuscany highlights.


  • Tuscan Villa Accommodation (one location)
  • Cycle through the countryside of Tuscany
  • Wine Tastings & Picnic lunches along the way
  • Cooking Experience in Chianti
  • Iconic locations & Medieval towns
  • Authentic regional Food & Wine daily
  • 5

    Tour Experience

  • 5


  • 4.5

    Quality of Amenities

  • 4.5

    Dining Experience

  • 4.5

    Quality of Accommodation & Grounds

  • 4.5

    Tour Locations

Important Information

  • Overview
  • Itinerary
  • Pricing / Date
  • Inclusions
  • Getting There
  • Accomodation

Our leisurely cycling in Tuscany tour allows you to experience the Tuscan countryside in a unqiue 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 7 day Taste of Tuscany tour connecting you with the locals and indulging in traditional food and wine daily.

  • Saturday
  • Sunday
  • Monday
  • Tuesday
  • Wednesday
  • Thursday
  • Friday
  • Saturday


We transfer you to your accommodation and allow you to settle in and familiarise yourself with your new surroundings which will be “home” for the next 7 days. Dinner in Cortona.

Cortona Hillside Cycling & Township

Today we will spend the morning cycling the Hillside of the 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 regional dishes.
After lunch you will have some free time to explore and get to know this beautiful township; Visit the many boutiques, art galleries, stroll to the “high point” and visit Chiesa di Santa Margherita, where the Saint’s remains are encased high on the altar. Return to the villa by bike or car mid to late afternoon for a little relaxation by the pool before dinner in Cortona.

Siena & San Gimignano

We travel to Siena, a visit to the spectacular Piazza del Campo, where the famous bareback horserace is held. Visit Il Duomo and The Mangia Tower or simply stroll the streets and enjoy the ambience and the various delights Siena has to offer, from the little food stores which offer lots of tempting treats to the beautiful stores offering hand painted ceramics and leatherware. From there we visit San Gimignano for the afternoon. This is a beautiful medieval township which really is 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 simply sit and enjoy a delicious gelato. Dinner in Cortona

Cycle Lake Trasimeno

Today we 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 catching a ferry across to Isola Maggiore where we will spend a few hours. There will be the option to then ride back to Cortona or to be picked up by car. Dinner in Cortona

Tour Free Day

Today you may choose to “stay in” enjoy the pool and relax. Alternatively you may choose to visit a local township where you can spend the day “exploring”. We will arrange transportation to and from our local train station. Dinner in Cortona.

Chianti & Cooking Experience

This morning we will head towards the Chianti area and spend the morning with Laura in a 15th century Italian Cottage where she will impart her knowledge and passion of cooking. During the course of this day we will interact with the winemakers of this family run establishment. Lunch will be enjoyed overlooking the spectacular undulating landscape of vineyards and olive groves.

Location for dinner will be decided on the day.

Cycle Montepulciano Countryside

Spend the day exploring the stunning countryside of Montepulciano. We will ride to a local Vineyard where we will meet the wine makers, and of course enjoy a wine tasting & lunch. Return to the villa mid afternoon. Dinner in Cortona


After a leisurely breakfast we transfer you to the local train station for your onward travels.


Tour Cost: USD $3,895 per person, twin share.

Single Occupancy : USD $300



Available for commencement every Saturday through to 8th September.
Minimum 2 participants required for departure.

Available for commencement every Saturday from 4th May through to 7th September.
Minimum 2 participants required for departure.

Chat to us more if you are looking for a tour outside these dates

Tour cost includes:

  • 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 and the Medieval township of Cortona on the hilltop. The apartments within the villa are fully self-contained and will be entirely for your use, either one, two or three bedrooms, spacious living area and fully equipped kitchen, bathroom and laundry facilities.
  • Bi-Lingual Hosts for the duration of your tour
  • 5 day tours to itinerary locations
  • All breakfasts (continental)
  • Welcome pack of local delicacies and seasonal fruit
  • Complimentary bottle of wine & beer
  • 5 Light lunches (eg.pizza/panini/ salad)
  • 7 dinners (a-la-carte) at a local trattoria or restaurant. Wine included with dinner
  • Bikes and helmets for cycling days
  • Drink Stops for cycling days
  • Cooking Experience in Chianti
  • All travel to and from tour locations as detailed on itinerary
  • Ferry tickets for travel to Isola Maggiore
  • Wine tasting at selected vineyards/ establishments
  • Maps for all itinerary locations
  • Transfers to local train station or Cortona on tour free days
  • Transfers to and from the local train station on your arrival and departure days
  • Free access to Wi-Fi at the villa

What is not included in tour cost:

  • All items not detailed in inclusions
  • Personal spending
  • Tickets for museums/monuments
  • All transfers other than to the local train station


We are located near Cortona; 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).


Please contact us for prices.


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:

  • Take the Leonardo Express Train from Rome Airport to Roma Termini Train Station
  • (This is a 30min journey and will cost approximately 15 Euro)
  • 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:

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

Located in the valley, near the historical centre of Cortona (approx. 10km), the accommodation, a Tuscan villa with old world rustic charm, is your home base for the duration of the tour. Unpack, settle in to your own private apartment and commence your Tuscan experience.

Set on wonderful grounds with a spectacular pool and all modern facilities, including laundry, it overlooks the Val di Chiana and the historical centre of Cortona. On your tour free days take advantage of the country setting, pick fruit from the trees, stroll through the lush Italian countryside or simply enjoy reading a book by the pool under the Tuscan sun.

Learn More About Accommodation >

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After travelling through Europe for four weeks and having some amazing experiences like witnessing the July 14th fireworks at the Eifel Tower, and standing on snow-capped Alps, we didn’t think our trip could get any better. But we were wrong! Spending a week in a beautiful Tuscan Villa, with magical views and two fantastic hosts, has definitely been a highlight. Ines & Monique took care of everything and nothing was too much trouble. Thank You Monique & Ines for an unforgettable week in beautiful Tuscany.

- Linda & Paul - Australia

We had a magic week with Ines & Monique. Everything was provided for and we enjoyed our travels in Tuscany. We would come back any day. Try it!

- Jenni & Lawrie - Australia

Get in touch with us

Australia (+61) 400 191 511

Italy (+39) 331 4253965


Alternatively, fill in the form to enquire about our tours