Cycle the rolling hills surrounding Cortona for an unforgettable week long holiday in Tuscany. From your gorgeous villa, you will explore each day the nearby medieval villages, and make stops along your journey at delicious trattorias for sneaky little lunches. Indulge in a local cooking experience, and visit beautiful Lake Trasimeno. For the wine lovers, you'll be pleased to know that your cycle path takes you through Chianti and Montepulciano, complete with vineyard visits and tastings.
SAT / 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 7 days. Dinner in Cortona.
SUN / CYCLE CORTONA & COUNTRYSIDE
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.
MON / SAN GIMIGNANO & SIENA
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.
TUE / CYCLE TO LAKE TRASIMENO & COOKING EXPERIENCE
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.
WED / TOUR FREE DAY
You may choose to ‘stay in’ enjoy the pool and relax, visit Cortona or another local township, alternatively, you may choose from one of our additional activities that we have on offer, these vary from and are not limited to; Vespa tours, cycling tours, cooking classes, gelato making classes, painting classes, hot air ballooning. Dinner in Cortona.
THU / 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.
FRI / CYCLE MONTEPULCIANO COUNTRYSIDE
Spend the day exploring the stunning countryside of Montepulciano in the Val d’Orcia. We will drive to a commencement point and from there ride the countryside of the Val D’Orcia. We will enjoy a wine tasting and lunch. You will have some free time to explore this beautiful town. Return to the villa mid-afternoon. Dinner in Cortona.
SAT / DEPARTURE
After a leisurely breakfast, we transfer you to the local train
station for your departure.
Seven nights in a Tuscan villa
Bilingual Hosts for the duration of the tour
Day tours to itinerary locations
All dinners (a-la-carte) at a local trattoria or restaurant with wines
Complimentary bottle of wine and beer
Bikes, helmets & guides for cycling days. Approx 40km per day
Ferry tickets for travel to Isola Maggiore
Wine tasting at selected vineyards/establishments
All travel to and from tour locations as detailed on itinerary
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
Our various accommodations are nearby the historical centre of Cortona and set on wonderful grounds which include a swimming pool. The apartments within the villa comprise one/two/three bedrooms, living area, kitchen, bathroom and laundry facilities, comprising air-conditioning and WI-FI. Our accommodation options provide everything the traveller requires for a truly memorable Tuscan escape. Located in the valley approximately 10km from the historical centre of Cortona, the accommodations, which are restored Tuscan farmhouses with old world rustic charm, become home base for the duration of the tour, allowing the traveller to settle into their own private apartment and commence their Tuscan experience.