JUNE 21 2025
JUNE 28 2025
8 DAYS | 7 NIGHTS | ITALY
Bike Tuscany
Bike Tuscany
Join us for an unforgettable small group adventure in the picturesque region of Tuscany from June 21st to June 28th, 2025. Immerse yourself in the breathtaking landscapes and rich culture of Tuscany with the guidance of an excellent and dedicated private guide, exclusively available to your group.
You will be directed to our partner site for booking your plan
You will be directed to our partner site for booking your plan
8 days 7 nights
Cycling to Siena
San Gimignano
Tuscan Countryside
Ride to Chianti
Town of Murlo
TRIP
Itinerary
SCROLL FOR MORE
DAY 1: S.Q.O
San
Quirico d"Orcia
Welcome to Tuscany.
Kick off your adventure in the stunning Orcia Valley, nestled in the heart of Tuscany. Stay in the delightful hilltop towns of San Quirico d'Orcia or Pienza. Upon arrival, participate in a welcome briefing at the hotel, where our group will convene to outline the exciting itinerary and prepare for the days ahead. Meet and greet your super guide.
DAY 02: S.Q.O
Tuscan
Countryside Ride
Breakfast.
After breakfast, set off on a circular ride through the breathtaking Orcia Valley. Begin your journey from Pienza and San Quirico d'Orcia, and cycle to the picturesque wine town of Montepulciano, renowned for its Vino Nobile. Continue your ride to the medieval village of Monticchiello and visit the famous thermal spa of Bagno Vignoni before returning to your hotel.
Distance Covered: 35mi (56km)
Ascent: 2,969ft (905m)
Descent: 2,969ft (905m)
DAY 03: SIENA
Cycling
Vineyards to Siena
Breakfast.
Experience a scenic cycling adventure through picturesque Tuscany. Start in San Quirico and ride along back roads to the renowned wine town of Montalcino. Descend to Buonconvento, then ascend to the charming walled town of Murlo, passing through Bibbiano. From Murlo, tackle the short but steep Rospatoio Pass and enjoy a beautiful ride via Ville di Corsano. Conclude your journey in the splendid Gothic city of Siena, making this an unforgettable cycling day.
DAY 04: SIENA
Free day
in Siena
Breakfast.
Free day in Siena to immerse yourself in one of Italy's best-preserved medieval towns. Home to the grand Piazza del Campo, Siena offers a wealth of sights best explored on foot, despite its hilly terrain. Visit the stunning Duomo (cathedral) and numerous museums and historic buildings. Alternatively, opt for an unguided ride through the scenic surroundings. Whether you choose to explore or relax, Siena promises a memorable experience.
DAY 05: C. CHIANT
Gaiole
to Castellina
Breakfast.
From Siena, cycle directly into the heart of Chianti, exploring picturesque villages and stunning landscapes. The route takes you through beautiful hamlets and past spectacular vineyards and castles, including Castello di Brolio, where you can taste some of the finest regional wines. Continue to Gaiole for lunch and enjoy a gelato stop in Radda before completing the final section to Castellina in Chianti, where you'll stay for two nights.
Distance Covered: 32mi (51km)
Ascent: 3,307ft (1,008m)
Descent: 2,405ft (733m)
DAY 06: C.CHIANTI
San Gimignano
to Monteriggioni
Breakfast.
Start your journey from Castellina and cycle through the rolling Chianti countryside, enjoying a scenic descent into the lower valley. From Poggibonsi, head towards the iconic towers of San Gimignano, a UNESCO-recognized town famed for its medieval architecture, Vernaccia wine, and saffron. Spend a few hours soaking in the atmosphere, strolling along the ancient walls, and admiring the impressive towers. The return journey features a long but picturesque climb back to Castellina, where you can reward yourself with a well-deserved gelato.
Distance Covered: 47mi (75km)
Ascent: 3,957ft (1,206m)
Descent: 3,957ft (1,206m)
DAY 07: FLORENCE
Cycle
to Florence
Breakfast.
Cycle to Florence via Panzano and Greve in Chianti Experience the final leg of your journey through the stunning Tuscan countryside, cycling from Panzano to the vibrant market town of Greve in Chianti. This route, considered one of the most scenic roads in Tuscany, links Florence to Siena via the picturesque Chianti hills. Upon arriving in Greve in Chianti, take time to admire the triangular piazza that hosts the famous Chianti wine festival. Continue your ride towards Strada and Impruneta, known for their terracotta production, and stop for lunch in Impruneta. Finish your ride by taking a panoramic road towards Florence, cycling all the way to Piazzale Michelangelo. Arrive in Florence in the early afternoon, allowing you to start exploring this magnificent Renaissance city. Visit the cathedral, the Baptistery of Saint John, and the iconic Ponte Vecchio, a medieval stone bridge lined with jewelers.
Distance Covered: 32mi (51km)
Ascent: 2,356ft (718m)
Descent: 4,012ft (1,223m)
DAY 08: FLORENCE
Trip Conclusion
in Florence
Breakfast.
Your cycling adventure concludes in Florence after breakfast. If you’d like to extend your stay and explore more of this magnificent city, please let us know. We can assist with additional accommodations and activities to make the most of your time in Florence.
TRIP
Itinerary
SCROLL FOR MORE
DAY 1: S.Q.O
San
Quirico d"Orcia
Welcome to Tuscany.
Kick off your adventure in the stunning Orcia Valley, nestled in the heart of Tuscany. Stay in the delightful hilltop towns of San Quirico d'Orcia or Pienza. Upon arrival, participate in a welcome briefing at the hotel, where our group will convene to outline the exciting itinerary and prepare for the days ahead. Meet and greet your super guide.
DAY 02: S.Q.O
Tuscan
Countryside Ride
Breakfast.
After breakfast, set off on a circular ride through the breathtaking Orcia Valley. Begin your journey from Pienza and San Quirico d'Orcia, and cycle to the picturesque wine town of Montepulciano, renowned for its Vino Nobile. Continue your ride to the medieval village of Monticchiello and visit the famous thermal spa of Bagno Vignoni before returning to your hotel.
Distance Covered: 35mi (56km)
Ascent: 2,969ft (905m)
Descent: 2,969ft (905m)
DAY 03: SIENA
Cycling
Vineyards to Siena
Breakfast.
Experience a scenic cycling adventure through picturesque Tuscany. Start in San Quirico and ride along back roads to the renowned wine town of Montalcino. Descend to Buonconvento, then ascend to the charming walled town of Murlo, passing through Bibbiano. From Murlo, tackle the short but steep Rospatoio Pass and enjoy a beautiful ride via Ville di Corsano. Conclude your journey in the splendid Gothic city of Siena, making this an unforgettable cycling day.
DAY 04: SIENA
Free day
in Siena
Breakfast.
Free day in Siena to immerse yourself in one of Italy's best-preserved medieval towns. Home to the grand Piazza del Campo, Siena offers a wealth of sights best explored on foot, despite its hilly terrain. Visit the stunning Duomo (cathedral) and numerous museums and historic buildings. Alternatively, opt for an unguided ride through the scenic surroundings. Whether you choose to explore or relax, Siena promises a memorable experience.
DAY 05: C. CHIANT
Gaiole
to Castellina
Breakfast.
From Siena, cycle directly into the heart of Chianti, exploring picturesque villages and stunning landscapes. The route takes you through beautiful hamlets and past spectacular vineyards and castles, including Castello di Brolio, where you can taste some of the finest regional wines. Continue to Gaiole for lunch and enjoy a gelato stop in Radda before completing the final section to Castellina in Chianti, where you'll stay for two nights.
Distance Covered: 32mi (51km)
Ascent: 3,307ft (1,008m)
Descent: 2,405ft (733m)
DAY 06: C.CHIANTI
San Gimignano
to Monteriggioni
Breakfast.
Start your journey from Castellina and cycle through the rolling Chianti countryside, enjoying a scenic descent into the lower valley. From Poggibonsi, head towards the iconic towers of San Gimignano, a UNESCO-recognized town famed for its medieval architecture, Vernaccia wine, and saffron. Spend a few hours soaking in the atmosphere, strolling along the ancient walls, and admiring the impressive towers. The return journey features a long but picturesque climb back to Castellina, where you can reward yourself with a well-deserved gelato.
Distance Covered: 47mi (75km)
Ascent: 3,957ft (1,206m)
Descent: 3,957ft (1,206m)
DAY 07: FLORENCE
Cycle
to Florence
Breakfast.
Cycle to Florence via Panzano and Greve in Chianti Experience the final leg of your journey through the stunning Tuscan countryside, cycling from Panzano to the vibrant market town of Greve in Chianti. This route, considered one of the most scenic roads in Tuscany, links Florence to Siena via the picturesque Chianti hills. Upon arriving in Greve in Chianti, take time to admire the triangular piazza that hosts the famous Chianti wine festival. Continue your ride towards Strada and Impruneta, known for their terracotta production, and stop for lunch in Impruneta. Finish your ride by taking a panoramic road towards Florence, cycling all the way to Piazzale Michelangelo. Arrive in Florence in the early afternoon, allowing you to start exploring this magnificent Renaissance city. Visit the cathedral, the Baptistery of Saint John, and the iconic Ponte Vecchio, a medieval stone bridge lined with jewelers.
Distance Covered: 32mi (51km)
Ascent: 2,356ft (718m)
Descent: 4,012ft (1,223m)
DAY 08: FLORENCE
Trip Conclusion
in Florence
Breakfast.
Your cycling adventure concludes in Florence after breakfast. If you’d like to extend your stay and explore more of this magnificent city, please let us know. We can assist with additional accommodations and activities to make the most of your time in Florence.
Pricing
Starts at
USD $2990
/ person
Learn more by clicking 'Book now' to know about more upcoming deals, offers
You will be directed to our partner site for booking your plan
What's
Included
Private Guide
Double room with breakfast
Luggage Transfer
Program as per description in air-conditioned vehicle
Van support
City taxes when applicable
What's not
Included
Air fares & City taxes
Personal expenses & Insurances
Tips for local guides and driver
Drinks and meals unless mentioned in the program
