The Heart of Tuscany
Dive into a Renaissance Landscape on this Quintessential Tuscany bicycle tour
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- A thorough daily itinerary
- Details for exact accommodations
- What to expect
- Travel planning tips
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There are few better ways to fully immerse yourself in this land of light, history, and vine than this quintessential Tuscany bike tour. Find yourself gliding down lanes gilded by the Tuscan sun for seven glorious days, as we bring you unforgettable cycling adventures in this most fabled of Italian regions.
From the quaint town of Radda in Chianti to the photogenic landscapes of San Quirico D’Orcia, our biking tour through the magnificent Tuscan countryside has, as its backbone, the famed Via Chiantigiana. Literally meaning “Chianti Street”, this most classic of Tuscany cycling routes reveals the heart of the Chianti wine region in all its splendor. Rich with color, all around are views worthy of a Renaissance painting—alive with bright wildflowers in the spring, darkened with crushed grapes in the fall.
Our Tuscany bike tour also features a visit to Siena, where a languid medieval air lingers amidst its twisting streets of warm ochre buildings. Strolling its narrow maze of cobblestone alleys you’ll make an amazing architectural journey. Explore delightful piazzas, intricate displays of masonry, and its superb marble cathedral, before climbing the Torre del Mangia, Siena’s most famous tower, to enjoy its breathtaking views.
Tour Essence
- Stay in Tuscany luxury hotels and countryside inns
- Learn more about Tuscan cuisine, its wines and its olive oils, with exclusive visits to the homes of local producers
- Memorable Tuscany cycling routes through the Chianti area
- Discover the UNESCO World Heritage Sites of Val d’Orcia and Siena
- Ride through the Crete Senesi on one of the most beautiful bike rides in Tuscany
- Immerse yourself in an authentic Tuscan lifestyle with a traditional cooking lessons
- Ride to Montalcino, home of the most famous Italian red wine: Brunello di Montalcino
What to Expect
Terrain
Rolling and hilly with breathtaking viewsStart Location
RaddaEnd Location
San Quirico D'OrciaMileage
Average Daily: 30 miles Total: 152 milesElevation
Average Daily: 3,464 ft Total: 20,784 ft
Once you have a trip confirmed, we will feed you a steady diet of additional pre-departure information that includes: How to train, prepare, pack and all the wonderful, inspirational and practical things you want and need to know before you go! Our Travel Advisors will be available to help plan your pre- and post-tour travel.
- Van support
- Guided walking tour of Siena
- Olive oil tasting
- Cooking lesson by a local chef
- 2 wine tastings
- Expert, bilingual guides
- Shuttles at the beginning and end of the tour
What’s Included
- Use of a carbon road bike, fully-equipped with a Garmin Edge Touring GPS
- Ciclismo Classico jersey
- Ciclismo Classico water bottle
- Two water bottle holders
- Map holder on handlebars and a Garmin Edge GPS
- Handlebar bag
- Tire pump
- Combination bike lock
- Gel-padded saddle
- Choice of pedals
- Card with your tour leaders’ mobile phone numbers
Pedal Options
- Flat pedals
- Half-toe pedals (without straps)
- Toe cage pedals
What’s Not Included
- Helmet
- Optional: clipless pedals with shoes
- Optional: your own saddle
- All accommodations
- All breakfasts
- 3 lunches + 1 picnic
- 5 dinners
Chianti is a wine practically synonymous with Italy itself, benefiting from an unparalleled terroir that nurtures the best in Italian reds—something you’ll quickly appreciate on our Tuscany cycling adventures. We’ll pedal first to Montalcino, hometown of the most famous Tuscan red, Brunello di Montalcino. We also track through Greve and Panzano, literally immersing ourselves in Chianti along the way!
Complemented by outstanding meals, you’ll also learn from the experts about the finer points of Tuscan cuisine, and its wonderful olive oils. Visiting the homes of renowned local producers (some of whom are your Ciclismo Classico guides), you’ll take part in cooking lessons in authentic Tuscan cuisine. We’ll also visit the UNESCO World Heritage Site of Val d’Orcia and ride the “Crete Senesi,” one of the most beautiful Tuscany bike routes.
2022
2023
Start Location
RaddaFly Into
FlorenceEnd Location
San Quirico D'OrciaFly Out Of
Florence or RomeRadda warm-up ride
Average Mileage
14/20 milesElevation Gain
1,144/1,888 ftRiding Terrain
Rolling with a few hillsAccommodations
Palazzo Leopoldo
Palazzo Leopoldo is a wonderful villa in 1800 style in the historical center of Radda in Chianti. The building dates back to 1300.
The Chianti
Meals Provided
Breakfast, DinnerAverage Mileage
30/44 milesElevation Gain
3,723/5,261 ftRiding Terrain
Rolling hills with one long climbMeals Provided
Breakfast, DinnerAccommodations
Palazzo Leopoldo
Palazzo Leopoldo is a wonderful villa in 1800 style in the historical center of Radda in Chianti. The building dates back to 1300.
Siena
Meals Provided
Breakfast, LunchAverage Mileage
33 milesElevation Gain
2,134/2,445 ftRiding Terrain
Rolling and a longer climb on the extra loopMeals Provided
Breakfast, LunchAccommodations
Hotel Palazzetto Rosso
Set in a redbrick building dating from the Middle Ages, this eclectic hotel is a 2-minute walk from the domed church of Santa Maria in Provenzano, a 6-minute stroll from the buzzy Piazza del Campo. Furnished in a contemporary style, the 9 rooms feature elements such as exposed ceiling beams, brick walls or terracotta floors. All come with air-conditioning, flat-screen TVs and free Wi-Fi. Suites add living areas (some with pull-out sofas) and/or fireplaces. Some quarters offer city views.
Siena & Monteriggioni Loop
Meals Provided
Breakfast, DinnerAverage Mileage
26.5 miles / optional rest dayElevation Gain
2,516 ftRiding Terrain
RollingMeals Provided
Breakfast, DinnerAccommodations
Hotel Palazzetto Rosso
Set in a redbrick building dating from the Middle Ages, this eclectic hotel is a 2-minute walk from the domed church of Santa Maria in Provenzano, a 6-minute stroll from the buzzy Piazza del Campo. Furnished in a contemporary style, the 9 rooms feature elements such as exposed ceiling beams, brick walls or terracotta floors. All come with air-conditioning, flat-screen TVs and free Wi-Fi. Suites add living areas (some with pull-out sofas) and/or fireplaces. Some quarters offer city views.
Siena to San Quirico D'Orcia
Meals Provided
Breakfast, Lunch, DinnerAverage Mileage
41/53 milesElevation Gain
3,498/4,447 ftRiding Terrain
Rolling with some climbsMeals Provided
Breakfast, Lunch, DinnerAccommodations
Palazzo del Capitano
The 4-star Palazzo del Capitano is a restored ancient mansion from the 15th century and combines tradition with modern comforts.
Loop to Montalcino
Meals Provided
Breakfast, Picnic, DinnerAverage Mileage
34/36 milesElevation Gain
3,952/4,227 ftRiding Terrain
Lots of ups and downs with some long climbs and a section of gravel on the extra loopMeals Provided
Breakfast, Picnic, DinnerAccommodations
Palazzo del Capitano
The 4-star Palazzo del Capitano is a restored ancient mansion from the 15th century and combines tradition with modern comforts.
