Whole Journeys: Toscana in Bicicletta
Itinerary SummaryPedaling Provence.
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!View Day-by-Day ItineraryHide Day-by-Day Itinerary
Day 1: Arrival in Florence, transfer to 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.
Activity: city walking, approximately 2 hoursLodging: Locanda San Martino
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). Distance: 63 km (39 mi) with 4,700 feet of climbingLodging: Locanda del Loggiato
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.
Distance: two options: 38 km (24 mi) with 3,300 feet of climbing or 51 km (31 mi) with 4,600 feet of climbingLodging: Locanda del Loggiato
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. Distance: 40 km (25 mi) with 3,250 feet of climbingLodging: Villa Borgo Casabianca
Day 5: Cycle to Cortona or rest day
Highlights: optional ride to Cortona or rest day
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.
Distance: optional: 37 km (23 mi) with 3,000 feet of climbingLodging: Villa Borgo Casabianca
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.
Distance: 67 km (42 mi) with 4,800 feet of climbingLodging: Fattoria La Valle
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.
Distance: 66 km (41 mi) with 6,200 feet of climbingLodging: Fattoria La Valle
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!
HighlightsTour Siena's open markets with a local guide, cycle to Tuscan hilltop towns, cooking lesson in Bagno Vignoni, wine, olive oil, and pecorino cheese tastings, vist Tuscan producers and farmersKeep in Mind: We work hard to maintain consistency across all of our tours, but some trips have unique differences. Here are some things to keep in mind about this tour.
IncludesUse of a high quality 27-30 speed bike, 8 days, 7 nights' accommodation; 6 dinners with wine, & 7 breakfasts; special visits listed in the itinerary; cue sheets with supplemental chalk-dust arrows in town
Begin/EndSiena / Florence
Arrive/DepartFlorence International Airport (FLR) / Florence
Total Distance311-324 km (194-201 miles)
Daily DistanceAverage 52 km (32 miles)
Rating301-401 301 riders may want to take advantage of the rest days on this tour.
TermsTerms & Conditions
Dates Price Single Supplement Notes
* We are happy to match solo travelers who would like to share a room with someone of the same gender. If no match exists, due to hotel pricing, we will charge 50% of the single supplement rate. This fee will be collected at the time of the final payment. If a roommate assignment is available this fee will be refunded at the conclusion of the tour.