Itinerary Photos

Clay hills with a gentle profile on the curvilinear sides, cultivated with olive groves and vineyards, and at the wooded tops, winding streets, in beaten earth or gravel, medieval villages enclosed within ancient walls. Pasty, chalky colors. A harmonious landscape, where everything has its place, enchantingly, as in a Renaissance painting. For those who love to travel by bicycle, Tuscany is undoubtedly a perfect destination, especially if you choose its southern portion, between the provinces of Arezzo and Siena, where we can find a concentration of some of the most splendid art cities in the whole region and some world-famous food and wine districts, such as Chianti and Val d’Orcia. Here you really will pedal into a dream.

Detailed Tour Program

Travel Tuscany Cortona
1° day: Rome - Cortona

Arrive at Rome airport, meet with the driver and get settled for a private transfer to Cortona.
After arriving and checking-in at the “Relais il Falconiere”, take the opportunity to rest in the beautiful swimming pool of the hotel, admiring the Tuscan hills and beautiful views of Cortona. At the end of the afternoon we suggest a beautiful walk through lovely Cortona and a dinner at the restaurant “Bottega Baracchi”.
Cortona, which was founded by the Etruscans, is one of the oldest and most beautiful cities in the region; within its various attractions, its medieval buildings are what stand out in particular: the “Palazzo Comunale”, located at Piazza Della Repubblica, the Museum “Dell’Academia Etrusca”, where the city’s history is told through the ancient Etruscan, Roman and Egyptian pieces exhibited there and the Diocesan Museum and Church of San Francesco, built in 1245.

viaggio In Italia Umbria Lago Trasimeno
2° day: Cortona / Val di Chiana / Lake Trasimeno (35 km with e-bike)

After breakfast, meet with the e-bike tour leader at the hotel, who will assign your bikes and brief you on the day ahead.  After leaving the hotel, pedal through the Val di Chiana region and discover famous wineries before reaching the shores of Lake Trasimeno in the small town of Castiglione del Lago, where you will be able to admire its fortress with a beautiful view of the lake. At the end of the tour, stop at the “Baldetti Winery”, producer of fragrant extra virgin olive oil and famed wine “Terre di Arezzo”; have lunch with stunning views of the lake and Cortona. Return to the hotel and relax before dinner; we suggest the 1* Michelin restaurant at the Relais il Falconiere.

Travel Italy Siena Chianti UNESCO
3° day: Cortona - Val di Chiana - Val D'Orcia - Montepulciano (43 km with e-bike)

After breakfast at the hotel, get ready to meet your e-bike tour leader and depart for a beautiful tour that begins in the Val di Chiana region, famous for producing Syrah wine, and continue on to the beautiful Val d’Orcia region. Val d’Orcia is a splendid mosaic of artful nature that has always fascinated artists, writers and poets. In the Renaissance era, the greatest painters immortalized the natural landscapes of Val d’Orcia, which became the symbol of prosperity and purity. Here you can find villages, abbeys, forts, spas and gardens, but also many charming panoramas and walks. Along the route you can also reach the village of Montepulciano located on top of a hill, famous for its medieval features. Characterized by stone constructions, buildings from the Renaissance era, the famous “Montepulciano Nobile” wine, considered one of the best in Italy, and the “Rosso de Montepulciano” wine. Stop for lunch at the “Podere il Casale” winery, renowned for its cheese production. Return to Relais il Falconiere, relax and if you feel like it, take a beautiful walk to admire the city of Cortona and have dinner at the restaurant “Il Preludio”.

4° day: Cortona - Siena - Castelnuovo Berardenga

Today after breakfast travel by minivan to Siena, and get ready to enjoy a 3-hour guided city tour after arrival. Siena is the homeland of Tuscany’s most celebrated festival, the “Palio di Siena”, a horse race held twice a year, a historical secular tradition strictly connected with the origin of the “Contradas” of Siena (districts into which the town is divided) and is run to celebrate the miraculous apparition of the Virgin Mary near the old houses that belonged to Provenzano Salvani. Visit the Church of San Domenico, where the relics of Santa Catarina da Siena are laid to rest. Admire the medieval buildings decorated by the standards of the winners of the last Palio through the alleys of the city and stare in wonder at the most beautiful square in the city: “Piazza del Campo”. Here you can find the “Palazzo Comunale”, the city hall built in the XIV century, the Bell Tower and the “Fonte Gaia”. At “Piazza del Duomo” you will find an impressive work of art: the Cathedral, with its main façade in the Romanesque- Gothic style, influenced by the Pisa school. Enjoy the rest of the day at leisure. Lunch is free, so take the opportunity to indulge in one of the great restaurants in “Piazza del Campo” and enjoy a little more of the city’s beauty.  For art lovers, there’s nothing better than to visit the Pinacoteca Nazionale.  In the late afternoon you will be driven to “Castel Monastero” to check-in and relax.

5° day: Castelnuovo Berardenga - Chianti - Villa Sesta - Castello di Brolio (30 km by e-bike)

Meet with the e-bike tour leader after breakfast and start discovering the wonderful Chianti areaSpend the day pedalling along a beautiful trail where famed wineries “Villa a Sesta” and “Castello Bossi” can be found, and indulge in a sumptuous lunch at the beautiful “Castello di Brolio” while sampling their wonderful wines; alternatively you could enjoy a complete picnic surrounded by nature. Return back to the hotel, relax, recharge and get ready for a new day.

Travel Tuscany San Gimignano
6° day: Castelnuovo Berardenga - San Gimignano - Castelnuovo Berardenga

Today is dedicated to the discovery of the surroundings of Castelnuovo Berardenga and San Gimignano in the comfort of a car with a private driver, who you will meet after breakfast. The small town of San Gimignano is located in the charming region of Tuscany, about 40 kilometers from Siena and 60 kilometers from Florence, and is perfect for a day visit. With only seven thousand inhabitants, the medieval village dates back from the X century; a good part of its original architecture is well preserved there, like buildings, monuments and, mainly, towers. The Italian gelatos’ fame is undeniable, and the “Gelateria Dondoli” of San Gimignano has received the world title for best gelato for three consecutive years thanks to its numerous flavors, including some specials such as gorgonzola with nuts, herb cream and black olives. Today lunch is scheduled at a winery that produces “Vernaccia” white wine, one of the oldest in the world. You will then get taken back to the hotel to relax and prepare for the evening.

Travel Tuscany Crete Senesi Bike Tour
7° day: Castelnuovo Berardenga - Crete Senesi - Castelnuovo Berardenga (38 km with e-bike)

Today after breakfast and the meeting with the e-bike tour leader, get ready to discover the famous “Crete Senesi”. The region called “Crete Senesi” is close to the southeast of Siena, (15 min), between the cities of Asciano, Buonconvento Monteroni D’Arbia, Rapolano Terme and San Giovanni D’Asso, which you will pass through with your e-bike. The landscape of the “Crete Senesi” varies a lot with the seasons, and it has a predominant color in each one, sometimes gray due to the clay, yellow due the sulfate, green due to the germinated fields; in early summer they turn yellow along with the flowers, and after August, when the grain and sunflowers are harvested, they turn brown again. Enjoy lunch at a typical “agriturismo” where you can eat the famous pork dish called “Cinta Senese”: these Sienese pigs live in the wild or semi-wild and are a medium sized breed, with a dark coat and the characteristic white band surrounding their chest and paws.

Florence Skyline Night UNESCO Travel Italy
8° day: Castelnuovo Berardenga - Florence or Rome

Enjoy breakfast at the hotel before your private transfer to the airport.



Your tour package includes: