Country
Tuscany · Italy
Duration
6 days · 5 nights
Profile
Hilly
Supported Tour
Van support
Private Tour
Your group. Your dates.
The Experience: Tuscany’s Golden Hills & Renaissance Heritage
Embark on an extraordinary Tuscany cycling tour through the heart of Italy, discovering some of the world’s most iconic landscapes with Veymont Travel. This premium van-supported journey blends physical challenge, cultural exploration, and the legendary art of living, set against a backdrop of rolling cypress-lined ridges, historic villages, and world-renowned vineyards.
Starting in the Renaissance gem of Pienza, you’ll ride through the breathtaking Val d’Orcia, a UNESCO World Heritage Site celebrated for its harmonious blend of nature and culture. This idyllic region is the very image of Tuscany: gently undulating hills, medieval farmhouses, and fields that change with the seasons. It’s a land that has inspired artists and poets for centuries, and there is no better way to experience it than from the saddle.
Each day brings a new Tuscan treasure: the wine haven of Montalcino, the Gothic beauty of Siena, the famous hills of Chianti, and the medieval towers of San Gimignano. Designed for regular cyclists, this tour invites you to fully experience the Tuscan lifestyle, from scenic backroads to exceptional gastronomy. Let Tuscany unfold at the pace of your pedals—authentic, serene, and endlessly inspiring.
We will meet you at Pisa airport at a predetermined time before transferring you to your hotel in Pienza, a Renaissance jewel designed by Pope Pius II and home of our first night. In the afternoon, we will present the itinerary and adjust your bike setup before we enjoy our first moments of this Tuscany bike tour.
Meals: Dinner
Accomodation: Hotel Corsignano 4* – Pienza
Your first ride explores the heart of the Val d’Orcia, a UNESCO World Heritage site of unparalleled beauty before climbing towards Montalcino. This medieval stronghold, famous for its 14th-century fortress and world-renowned Brunello wine, offers panoramic views over endless vineyards and ancient olive groves.
Meals: Breakfast · Picnic / Lunch · Dinner
Route: 40 km / 800 m Elevation Gain
Accomodation: Hotel dei Capitani 3* – Montalcino
Today blends professional cycling legend with Gothic majesty as you head toward Siena. After passing the high-altitude vineyards of Corte Pavone, you will tackle the celebrated Strade Bianche, the historic white gravel roads that wind through the cypress-lined hills. The stage reaches a dramatic climax in the shell-shaped Piazza del Campo, the vibrant heart of Siena and home to the legendary Palio horse race.
Meals: Breakfast · Picnic / Lunch · Dinner
Route: 55 km / 1000 m Elevation Gain
Accomodation: Hotel Athena 4* – Siena
Pedal into the emerald hills of Chianti, a region synonymous with Italy’s finest ruby-red wines. You will visit the imposing Castello di Brolio, the 12th-century birthplace of Chianti Classico, and ride the legendary paths of L’Eroica. The day concludes in the fortified village of Radda in Chianti, where narrow cobblestone alleys and cozy enotecas invite you to embrace the authentic Tuscan art of living.
Meals: Breakfast · Picnic / Lunch · Dinner
Route: 50 km / 1000 m Elevation Gain
Accomodation: Relais Vignale Hotel & Spa 4*
The final stage connects two of Tuscany’s most striking fortifications. After passing the “crown-like” fortress of Monteriggioni, the skyline of San Gimignano appears on the horizon. Known as the Medieval Manhattan for its fourteen soaring stone towers, this town offers a spectacular finish. Celebrate the journey’s end with a glass of crisp Vernaccia di San Gimignano as the sun sets over the rolling Tuscan horizon.
Meals: Breakfast · Picnic / Lunch · Dinner
Route: 65 km / 900 m Elevation Gain
Accomodation: Hotel Casolare Terre Rosse 3* – San Gimignano
After a final breakfast in the charming Tuscan countryside, your journey concludes. Your guide will transfer you to Pisa Airport or Florence. This marks the end of your van-supported cycling tour in Tuscany, completing a deep exploration of Italy’s most iconic landscapes.
If you’ve been captivated by the rolling Tuscan hills, your next great challenge lies further North among the jagged peaks of the Dolomites — our ultimate high-altitude cycling journey in Italy.
Meals: Breakfast
IncluDED
Accomodation
- 2 night in 4* hotels in double occupancy
- 3 nights in 3* hotel or equivalent in double occupancy
Meals
- 5 breakfasts
- 4 picnics / lunches
- 5 dinners
- Sport nutrition for every day of cycling
Guiding
- 1 guide-driver with van who supports the group all along the tour
Activities
- 5 bike rides
Equipment
- Garmin GPS rental : 1 for 4 pers.
- 2 bottles
- 1 Veymont Travel cycling jersey
Support & Transfer
- Transfer of people
- Transfer of luggages
- Transfer of bikes
- Mechanical assistance
- Pick up and drop off at predeterminated places
Non Inclus Séjour Liberté
- Travel and repatriation insurance
- Plane/train tickets and transportation to/from predetermined pick up/drop off locations
- Accomodation before and after the stay
- Personnal effetcs purchased during the stay
- Activities not planned by Veymont Travel
- Meals not mentionned in the “meals” section
- Wine and dinks in bars, hotels and restaurants
- Bike rental
- Cycling guide
In option:
- Bike rental and equipment
- Room in Single occupation
- Cycling guide