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 Bagno Vignoni, we cycle through the Tuscan countryside along Via Chiantigiana (literally, Chianti Street). This classic and rustic route passes through the heart of the Chianti wine region. The landscape resembles a Renaissance painting alive with wildflowers in the spring and crushed grapes in the fall. Our Italian bike trip also features a visit to Siena, where a medieval air lingers amidst the twisting streets of warm, brown brick. Strolling Siena’s narrow maze of cobblestone walkways is a fantastic architectural journey – with its incredible masonry, delightful piazzas, a marble cathedral, Torre del Mangia, and breathtaking views from Siena’s famous tower!
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 luxury hotels and countryside inns
- Learn more about Tuscan cuisine, wines, and olive oil in exclusive visits to the home of local producers
- Enjoy memorable rides in the Chianti area
- Ride through the Crete Senesi on one of the most beautiful bike rides in Tuscany
- Discover the UNESCO World Heritage Sites of Val d’Orcia and Siena
- Immerse yourself in Tuscan lifestyle with a cooking class
- Ride to Montalcino, home of the most famous Tuscan red wine: the Brunello di Montalcino
- Experience an event that you will never forget: the Palio di Siena. See the detailed itinerary!
What to Expect
Terrain
Rolling and hilly with breathtaking viewsStart Location
RaddaEnd Location
Bagno VignoniMileage
Average Daily: 25/35 miles Total: 180/220 milesElevation
Average Daily: 2,700/3,400 ft Total: 16,200/20,200 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
- Service of local, professional guides throughout the program
- Ciclismo jersey and water bottle
- Cycling clinics
- Cooking class by a local chef
- Olive oil tasting
- 2 wine tastings
- Guided walking tour of Siena
- Shuttle at the beginning and end of the tour
What’s Included
- Use of our exclusive carbon road bike, La Classica Ribelle (or Equivalent Carbon Road Bike)
- Garmin Edge Explore GPS loaded with the GPX tracks of your rides
- Two water bottles
- Saddle bag with repair kit
- Optional: Map holder on handlebar
Pedal Options
- Flat pedals
- Half-toe pedals (without straps)
What’s Not Included
- Helmet
- Optional: clipless/SPD pedals with shoes
- Optional: your own saddle
- All breakfasts, 3 lunches, 1 picnic, 4 dinners
- All accommodations:
- Day 1 & 2: Relais Vignale
- Day 3 & 4: Palazzetto Rosso
- Day 5 & 6: L’Orto delle Terme
Chianti is a wine practically synonymous with Italy, benefiting from an unparalleled terroir that nurtures the best in Italian reds—something you quickly appreciate on our Tuscany cycling adventures. We pedal first to Montalcino, the hometown of the most famous Tuscan red, the Brunello di Montalcino. We also track through Greve and Panzano, immersing ourselves in Chianti along the way!
Complemented by outstanding meals, you also learn from the experts about the finer points of Tuscan cuisine and its excellent olive oils. Visiting the homes of renowned local producers (some of whom are your Ciclismo Classico guides), you take part in cooking class in authentic Tuscan cuisine. We also visit the UNESCO World Heritage Site of Val d’Orcia and ride the “Crete Senesi,” one of the most beautiful Tuscany bike routes.
2026
Start Location
RaddaFly Into
Florence or RomeEnd Location
Bagno VignoniFly Out Of
Florence or RomeRadda warm-up ride
Meals Provided
Lunch, DinnerAverage Mileage
15 / 20 milesElevation Gain
1,100 / 1,900 ftRiding Terrain
Rolling with a few hillsMeals Provided
Lunch, DinnerAccommodations
Relais Vignale
Relais Vignale & Spa is a charming 4-star hotel set in an 18th-century villa in the heart of Radda in Chianti. It offers traditionally styled rooms, a heated outdoor pool with countryside views, a relaxing spa, and a restaurant serving classic Tuscan cuisine—an ideal setting for a refined and peaceful Chianti getaway.
The Chianti
Meals Provided
Breakfast, DinnerAverage Mileage
30 / 45 milesElevation Gain
3,700 / 5,300 ftRiding Terrain
Rolling hills with one long climbMeals Provided
Breakfast, DinnerAccommodations
Relais Vignale
Relais Vignale & Spa is a charming 4-star hotel set in an 18th-century villa in the heart of Radda in Chianti. It offers traditionally styled rooms, a heated outdoor pool with countryside views, a relaxing spa, and a restaurant serving classic Tuscan cuisine—an ideal setting for a refined and peaceful Chianti getaway.
Siena
Meals Provided
Breakfast, Lunch, DinnerAverage Mileage
30 / 30 milesElevation Gain
2,100 / 2,500 ftRiding Terrain
Hilly, and a longer climb on the extra loopMeals Provided
Breakfast, Lunch, DinnerAccommodations
Palazzetto Rosso
Palazzetto Rosso Boutique Hotel sits in the heart of Siena’s medieval center, its red brick walls welcoming travelers since the Middle Ages, when merchants from across the world passed through Tuscany. Though much has changed over the centuries, the hotel’s historic façade endures, adorned with traditional wrought-iron signs and architectural details that preserve its timeless charm.
Siena & Monteriggioni Loop
Meals Provided
BreakfastAverage Mileage
Rest day / optional 24-mile rideElevation Gain
1,800 ftRiding Terrain
RollingMeals Provided
BreakfastAccommodations
Palazzetto Rosso
Palazzetto Rosso Boutique Hotel sits in the heart of Siena’s medieval center, its red brick walls welcoming travelers since the Middle Ages, when merchants from across the world passed through Tuscany. Though much has changed over the centuries, the hotel’s historic façade endures, adorned with traditional wrought-iron signs and architectural details that preserve its timeless charm.
Siena to Bagno Vignoni
Meals Provided
Breakfast, Lunch, DinnerAverage Mileage
45 / 55 milesElevation Gain
3,500 / 4,500 ftRiding Terrain
Undulating with some climbsMeals Provided
Breakfast, Lunch, DinnerAccommodations
Albergo L’Orto delle Terme
L’Orto delle Terme offers a warm and authentic countryside stay in the peaceful Tuscan fields surrounding Bagno Vignoni. The rooms feature modern comforts such as air-conditioning, LCD TVs, WiFi, and thermal bath amenities, all set within a tranquil garden environment with easy access to the region’s renowned thermal spa facilities.
Loop to Montalcino
Meals Provided
Breakfast, Picnic, DinnerAverage Mileage
35 / 45 milesElevation Gain
4,000 / 4,300 ftRiding Terrain
Lots of ups and downs with some long climbsMeals Provided
Breakfast, Picnic, DinnerAccommodations
Albergo L’Orto delle Terme
L’Orto delle Terme offers a warm and authentic countryside stay in the peaceful Tuscan fields surrounding Bagno Vignoni. The rooms feature modern comforts such as air-conditioning, LCD TVs, WiFi, and thermal bath amenities, all set within a tranquil garden environment with easy access to the region’s renowned thermal spa facilities.
