This active foodie experience highlights the best food and wine Tuscany has to offer, with riding routes to challenge even the most active traveler. 

The regions south of Florence and Siena produce some of the most renowned red wines in the world. We start in Siena and ride south to Bagno Vignoni – set among the impressive background of the low, sweeping hills of the Val D’Orcia. Medieval and Renaissance history seep through the stones of small hilltop towns as the aromas of the winelands permeate the air. Wine tastings, wine cellar visits and a cooking class bring local specialties alive. The last few days we’ll cycle through the Chianti Classico region, characterized by short and steep hills dotted with vineyards and forest. This is the perfect tour for those who enjoy pedaling, and indulging in Tuscan delicacies!

DAY 1: Arrival in Florence, transfer to Siena

Highlights: Siena

            Often described as Italy's best-preserved medieval city, Siena rivaled Florence for dominance in Tuscany during the 1300s. We'll have an early afternoon tour of this historical city that captures hearts and imaginations the world over, and learn about the famous Palio – the horse race that takes place twice a year in the main square – and about the culinary specialties of Siena.

            Our hotel for the night is located in Palazzo Zaicchetti in the heart of Siena, and has

maintained its original structure. It’s the ideal place to experience the alluring charm and the atmosphere of this city that has maintained its medieval identity over the centuries.

            This evening, we’ll meet over wine for introductions before our first dinner together where we begin our deeper exploration of the region’s specialties. Simple recipes highlighting local fresh ingredients are the hallmarks of this area’s traditional cuisine. Their food culture features specialties such as sweet ricciarelli (a traditional biscuit with origin in Siena dating to the 14th century) and panforte (a traditional dessert containing fruits and nuts, and resembles fruitcake or Lebkuchen, dating back to 13th century Siena), paired with good wines.

Overnight in Siena

Activity: City walking, approx. 2 hours

DAY 2: Cycle to Bagno Vignoni

Highlights: A Roman and medieval spa town; vineyards, hilltop villas and views

            We head south from Siena today and ride along the clay hills of Le Crete Senesi, where bold clay hills create a surreal landscape, and the rolling hills are broken only by the cypress trees lining each road. On the way to our hotel, we recommend a stop at the Abbazia Monte Oliveto Maggiore, a Benedictine abbey built in the 13th century and famous for its frescoed cloister and stunning setting.

            We’ll continue south into the Orcia Valley, famous for its undulating hills and sweeping vistas to Bagno Vignoni, a Roman and medieval spa town. Our accommodation for the next two nights is a re-structured antique building from the 12th century, nestled in the town’s small square.

            Be sure to try typical specialties such as pecorino di fossa sheep’s cheese with marmalade and honey, and fantastic local meat such as the very tender meat known as chianina, from the local breed of cattle. Look out for spiedini di cinta senese (a particular pig which is black with a white belt around its neck or hips).

Overnight in Bagno Vignoni

Activity & Distance: Cycling approx. 63km (39 mi), with 4,700 feet of climbing

DAY 3: Loop Ride to Montalcino

Highlights: Orcia Valley, Abbey of Sant’Antimo, wine town of Montalcino, visit to an olive oil press, cooking class and wine tasting

            Our loop ride today takes us to San Quirico d’Orcia where we can stop and visit an olive oil press, one of the few in the center of a medieval town. Our midway point on our ride today is the famous wine town of Montalcino. This fortified town was used as a shelter by Sienese nobles during the 16th century, but is more famous today for producing one of Italy’s premier red wines, Brunello di Montalcino. We suggest you grab lunch here before heading off towards the eighth century Saint’Antimo Abbey. From here, anyone wanting to shorten the ride will be shuttled back to our hotel, while those looking for more miles can continue on.

            There may be a cooking class this afternoon near Bagno Vignoni, and a wine tasting this evening, before we disperse for dinner.

Overnight in Bagno Vignoni 

Activity & Distance: Two cycling options: 38km (24 miles) with 3,300 feet of climbing or 51km (31 miles) with 4,600 feet of climbing

DAY 4: Cycle to Pienza and Trequanda

Highlights: Pienza; Pecorino di Pienza tasting

            We leave the Orcia Valley behind and pedal north today. The first stop on our route is Pienza, home of Pope Pius II who, with the help of a number of renowned architects, turned this tiny

village into a showpiece of Renaissance architecture and urban planning in the 16th century. Here, we’ll have a chance to see and taste the famous Pecorino di Pienza; sheep’s milk cheese.

Our 4-star hotel for the next two nights is a restored medieval estate and villa. The 18th century manor house has three rooms and six suites, some of which still have original frescoes.

Overnight in Asciano 

Activity & Distance: Cycling 40km (25 miles) with 3,250 feet of climbing

DAY 5: Cycle to Cortona or rest day

Highlights: Optional ride to Cortona or day of rest

            We have an optional ride planned for today; if you do decide to cycle, we suggest you visit the beautiful town of Cortona – the main cultural and artistic center of the Val di Chiana – for lunch, before looping back to our hotel to relax by the pool, (or take a shuttle).

            For those who would like to stay put, this would be a perfect day to rest and relax by the pool and enjoy our surrounds. The restaurant serves local Tuscan specialties of the Chiana Valley – of Siena and of Tuscany – reflecting their knowledge of the Mediterranean diet, accompanied by an excellent wine list.

Overnight in Asciano 

Activity & Distance: Optional cycling, 37km (23 miles), with 3,000 feet of climbing

DAY 6: Cycle to Panzano in Chianti

Highlights: Ride through famous wine regions; medieval village

            The views change from the soft hills of southern Tuscany to striking short and steep hills as we pedal north in the Chianti region, one of the most famous wine regions of Italy. Small towns dot our route on our way to the medieval village of Panzano in Chianti and our country hotel for the next two nights. Overlooking the most famous vineyards of the prestigious Conca d'Oro in Chianti, Fattoria la valle is located only three kilometers from Panzano.

Overnight in Panzano in Chianti

Activity & Distance: Cycling approx. 67km (42 miles), with 4,800 feet of climbing

DAY 7: Loop Ride in Chianti

Highlights: Ride through beautiful valleys and iconic vineyards; possible wine tasting

            Today we take in the beauty of the valleys of the Chianti area. Our ride takes us through Radda and Gaiole, and some of the most iconic vineyards in Italy. We promise that by the end of today, you’ll understand why Tuscany’s allure is so strong. We may also enjoy a wine tasting en route.

Overnight in Panzano in Chianti 

Activity & Distance: Cycling approx. 66km (41 miles), with 6,200 feet of climbing

DAY 8: Transfer to Florence

After breakfast in the hotel, we’ll shuttle to Florence, where you’ll hopefully plan some time to explore this stunning city; visiting Michelangelo’s David at the Accademia, Botticelli’s Birth of Venus and the other masterpieces of the Uffizi Gallery, and whatever else catches your eye. Have a great trip!

Drop-off:  Florence, Italy

Transfer Times: 1.5 hours to Florence

TOUR DETAILS