Heart of Tuscany
Dive into a Renaissance Landscape on this Quintessential Tuscany bicycle tour
Download a Detailed Itinerary
Our comprehensive itineraries are a one-stop-shop for all the delightful details of our carefully crafted tours, including:
- A thorough daily itinerary
- Details for exact accommodations
- What to expect
- Travel planning tips
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This Ciclismo Tuscan exclusive is super popular with private groups. Are you and your friends dreaming of Cycling in Tuscany? Consider making this Classico tour private! Contact: [email protected]
This Ciclismo Tuscan exclusive is super popular with private groups. Are you and your friends dreaming of Cycling in Tuscany? Consider making this Classico tour private! Contact: [email protected]
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
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
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 is a welcoming 3-star retreat located just steps from the historic thermal village of Bagno Vignoni. Surrounded by the peaceful Val d’Orcia countryside, the property offers comfortable, rustic-chic rooms.
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 is a welcoming 3-star retreat located just steps from the historic thermal village of Bagno Vignoni. Surrounded by the peaceful Val d’Orcia countryside, the property offers comfortable, rustic-chic rooms.
Arrivederci!
Meals Provided
BreakfastMeals Provided
BreakfastAccommodations
2027
Once your trip is confirmed, we’ll provide everything you need to prepare for your adventure—from training and packing tips to practical travel information and inspiration to get you excited for the journey ahead. Our Travel Advisors are also available to help you plan your pre- and post-tour travel.
- Services of expert local bilingual guides throughout the program
- Full van support throughout the tour
- Ciclismo Classico Super Snacks with local specialties and fresh seasonal products
- Cycling clinics and personalized coaching
- Group shuttles at the beginning and end of the tour
- Cultural visits and entrance fees as per itinerary
What’s Included
- Use of our exclusive carbon road bike, La Classica Ribelle (or equivalent)
- Garmin Edge Explore GPS preloaded with daily routes and GPX tracks
- Ride with GPS navigation and route access for mobile devices
- Ciclismo jersey and water bottle
- Saddle bag with repair kit
- Optional map holder on handlebars
Pedal Options
- Flat pedals
- Half-toe pedals (without straps)
What’s Not Included
- Cycling helmet
- Optional clipless/SPD pedals and cycling shoes
- Optional personal 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
- Guided walking tour of Siena
- Cooking class with traditional regional specialties
- Olive oil tasting with extra virgin olive oil
- 2 wine tastings, including local Sangiovese and other regional varieties
