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Group discount Available

Brolio Castle Chianti Bike Tour

Cycle through the vineyards of Chianti to the historic Brolio Castle, where the story of Chianti wine was born. This one day bike tour blends...
Duration 8 Hours
€190
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Next Departures October 12, 2026 (Available)October 13, 2026 (Available)October 14, 2026 (Available)
Most Popular
Group discount Available

Crete Senesi Area to Pienza Bike Tour

Ride through the iconic Crete Senesi countryside and into the Renaissance jewel of Pienza. This one day bike tour blends strade bianche gravel sections, rolling...
3 People
Duration 8 Hours
€190
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Next Departures October 12, 2026 (Available)October 13, 2026 (Available)October 14, 2026 (Available)
Most Popular

Crete Senesi to Montalcino Cooking & Bike Tour

This 7-day guided cooking and bike tour is a celebration of Tuscany’s greatest pleasures — rolling hills, medieval villages, Brunello wine, handmade pasta, and the...
1 Person
Duration 7 Days - 6 Nights
€3,350
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Next Departures November 1, 2026 (Available)November 2, 2026 (Available)November 3, 2026 (Available)
Most Popular

Eroica Roads Gravel Self Guided Bike Tour

Self-guided gravel bike tour to discover the most beautiful roads of the Eroica. You'll start in Siena on the famous dirt roads of the Strade...
1 Person
Duration 6 Days - 5 Nights
€1,590
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Next Departures October 17, 2026 (Available)October 18, 2026 (Available)October 19, 2026 (Available)
Group discount Available

Cortona to Montepulciano Bike Tour

A relaxed one day bike tour linking two of Tuscany’s most famous towns — Cortona, made legendary by Under the Tuscan Sun, and Montepulciano, home...
3 People
Duration 8 Hours
€190
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Next Departures October 12, 2026 (Available)October 13, 2026 (Available)October 14, 2026 (Available)

Gaiole in Chianti Eroica Self-Guided Bike Tour

For gravel riding enthusiasts, this is Tuscany at its finest. Base yourself in the Chianti hills and ride loops each day that combine world-famous cycling...
Duration 6 Days - 5 Nights
€1,050
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Next Departures October 17, 2026 (Available)October 18, 2026 (Available)October 19, 2026 (Available)
Most Popular

Italy Coast to Coast bike tour

Is there a better long weekend of riding than this? Starting from the beach in Cattolica on the Adriatic sea, we ride into the heart...
1 Person
Duration 5 Days - 4 Nights
€1,350
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Next Departures November 1, 2026 (Available)November 2, 2026 (Available)November 3, 2026 (Available)

Pienza to Castelnuovo Berardenga Chianti Bike Tour

This 7-day guided bike tour is a full-immersion ride through the rolling hills, vineyard-covered valleys, and cultural gems of southern Tuscany. Beginning in the Renaissance...
1 Person
Duration 7 Days - 6 Nights
€3,150
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Next Departures November 1, 2026 (Available)November 2, 2026 (Available)November 3, 2026 (Available)
Most Popular

Pienza to Montalcino Self-Guided Bike Tour

Golden hills, quiet strade bianche, and world-class wines—welcome to Tuscany’s cycling postcard. On this self-guided bike tour, you’ll spin between hilltop villages, pause for cellar...
1 Person
Duration 5 Days - 4 Nights
€1,200
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Next Departures October 17, 2026 (Available)October 18, 2026 (Available)October 19, 2026 (Available)
Group discount Available

Pienza to Montepulciano Wine Bike Tour

A day of cycling, wine, and Tuscan beauty — all in one unforgettable experience. This one day bike tour takes you through the rolling vineyards...
3 People
Duration 8 Hours
€190
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Next Departures October 12, 2026 (Available)October 13, 2026 (Available)October 14, 2026 (Available)
Most Popular

Pienza to San Gimignano Bike Tour

This 8-day guided bike tour is a deep dive into Tuscany’s most picturesque landscapes and timeless towns. Beginning in the Renaissance gem of Pienza and...
1 Person
Duration 8 Days - 7 Nights
€3,150
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Next Departures November 1, 2026 (Available)November 2, 2026 (Available)November 3, 2026 (Available)
Most Popular
Group discount Available

Radda in Chianti Loop Bike Tour

Discover the castles and vineyards of Chianti on this one day bike tour. Starting near Siena, the ride loops into the lush valleys and rolling...
3 People
Duration 8 Hours
€190
View Details
Next Departures October 12, 2026 (Available)October 13, 2026 (Available)October 14, 2026 (Available)
Most Popular
Group discount Available

Rapolano Terme to Montalcino Bike Tour

From the thermal waters of Rapolano Terme to the vineyards of Brunello, this one day bike tour combines two Tuscan icons: hot springs and wine....
1 Person
Duration 8 Hours
€190
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Next Departures October 12, 2026 (Available)October 13, 2026 (Available)October 14, 2026 (Available)

Rapolano Terme to Monte San Savino Gravel Bike Tour

Explore Tuscany’s white roads, UNESCO valleys, medieval wine towns, and the Chianti hills on this 7-night and 8 day gravel bike tour. Starting in Rapolano...
Duration 8 Days - 7 Nights
€3,150
View Details
Next Departures November 1, 2026 (Available)November 2, 2026 (Available)November 3, 2026 (Available)