Tuscany Family Bike Tour
6 days
5 nights
Activity Levels 1-4
Premiere Hotels
Tuscany Family Bike Tour
6 days
5 nights
Activity Levels 1-4
Premiere Hotels
2026: Jun-Aug
Fun & Adventure from Montepulciano to Chianti
Bike past vineyards and valleys to gelato shops in ancient hill towns. Wine tasting for the adults. A high-ropes course and art for kids. Tuscan fun for everyone.
Highlights
- Explore medieval Montepulciano and ride the Road of the Castles to Radda in Chianti
- Bike through colorful fields of sunflowers, corn, wheat and tomatoes
- Visit hilltop Castiglione del Lago then descend to Umbria's Lake Trasimeno
- Dine at authentic trattorias and classic country villas serving up farm-fresh cuisine
- Swim or lounge poolside at historic Tuscan retreats
Start Arezzo
End Florence
* Start/End locations may vary. Do not book flights until your trip details are confirmed.
Itinerary
Days 1-2
Bike through the picturesque countryside of the Val di Chiana past cypress trees, sunflower fields, grazing sheep and farmhouses • Savor farm-fresh products over a family lunch prepared just for us • Follow cycling routes to the town of Castiglione del Lago, with views of the iconic Umbrian landscape and Lake Trasimeno • Kids have fun with water sports while the grown-ups bike rolling terrain back to Tuscany • Step back in time as you stroll the historic streets of Montepulciano • Lounge poolside at our hotel, a former medieval village and the ideal place for rest and play.
Nights 1-2
This 18th-century boutique retreat sits on a stunning plot with gardens, an olive grove and vineyard—where wine is produced onsite. (pool)
Day 3
Leave Val di Chiana behind as you cycle into the Crete Senesi, an area known for its lunar landscape • Reach the sleepy hill town of Asciano and stop by an agriturismo (working farm) for a taste of farm-fresh Tuscan food • Legendary wine villages like Castelnuovo Berardenga line your route as you bike with your family toward the heart of Chianti • Watch the sun set over the countryside from our hotel, an elegantly restored castle-hotel among vineyards and olive orchards.
Night 3
Stunning views of the Tuscan countryside and exceptional hospitality await at this elegantly restored castle-hotel. Leading Hotels of the World property. (pool, spa)
Days 4-6
Ride along the Strada dei Castelli (Road of the Castles) to Radda in Chianti and Castellina in Chianti, known today as two major centers for Chianti Classico wine production • Young artists try their hands at painting their own ceramic souvenirs in a fun art class • Bike scenic routes through Chianti's inviting hills • Shop for hand-painted souvenirs and admire Renaissance-style designs at Ceramiche Rampini • Kids visit a local artisanal shop and get creative in another painting activity • Pause to enjoy delicious gelato in ancient towns • Wonderful vistas abound during a ride through the heart of Chianti • Celebrate a Tuscan family vacation with a memorable dinner at our exclusive hotel.
Nights 4-5
In the heart of the Chianti, this impressively restored feudal settlement dates back over 1,000 years and is surrounded by vineyards and woods. Unwind in the infinity pool overlooking Tuscan vineyards. (pool)
What's Included
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Dates & Prices
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