
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

Cuisine & Culture in the Heart of Italy
Tuscany is not only a destination, it's a sublime experience. Pause on the cypress-lined roads overlooking terraced vineyards and snap a family photo. It's a wonder anyone ever finishes the bike rides when each view surpasses the last. And this is only a preview of what you'll see. Imagine the wines, flavors and luxuries you'll discover.
Highlights
- Discover medieval Montepulciano and ride the Road of the Castles to Radda in Chianti
- Bike through colorful fields of sunflowers, corn, wheat and tomatoes
- Explore 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

StartArezzo
EndFlorence
* 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 • Enjoy 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 • Have fun with water sports and 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 • Our hotel's terrace provides an idyllic venue for enjoying the sunset over the vineyard-strewn valley.





Night 3
A tranquil 16th-century villa with wooded grounds, an Italian-style garden and a small church with frescoes by Arcangelo Salimbeni. (pool)

Days 4-6
Ride along the Strada dei Castelli (Road of the Castles) to Radda and Castellina in Chianti, known today as two major centers for Chianti Classico wine production • Bike scenic routes through Chianti's inviting hills • Shop for hand-painted souvenirs and admire Renaissance-style designs • 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
See moreHotels
World-Class Hotels
Our hand-selected Premiere hotels offer exceptional hospitality and experiences as special as the regions we explore.
Hotels may vary based on departure. Any variations will be displayed when selecting a departure under Dates & Prices.
Nights 1-2
Premiere Hotel
This 18th-century boutique retreat sits on a stunning plot with gardens, an olive grove and vineyard—where wine is produced onsite. (pool)
Night 3
*Deluxe Hotel
A tranquil 16th-century villa with wooded grounds, an Italian-style garden and a small church with frescoes by Arcangelo Salimbeni. (pool)
Nights 4-5
Premiere Hotel
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)
Gallery












#MyBackroadsTrip
Bikes
Choose Your Perfect Bike
Our bikes are designed and built with specific cyclists and riding styles in mind, so we can always offer you a perfect ride. Please note that bike requests are subject to availability and prioritized based on the date they're submitted.

Included in your trip price
- Ideal for avid cyclists
- Redesigned for 2024
- Next gen titanium frame with carbon wheels
- Responsive, efficient and comfortable
- Drop handlebars only

Included in your trip price
- One of the lightest e-bikes available
- Provides plenty of power and more than enough battery
- Lower top tubes for easier mounting and dismounting
- Upright handlebars only
- Limited availability on Unplugged Bike Tours; learn more
Min. age to ride e-bike: 16+

- $400 rental fee
- Hand-built frame features Co-Motion's custom-designed Cro-Moly steel tubeset, powerful Avid disc brakes, Shimano Ultegra drive train
- Custom upgraded wheelset
- Best for riders with some tandem experience.
Dates & Prices
Dates & Prices
Click on dates for pricing, itinerary variations (if any) and to book your trip. Price is per person, double occupancy in USD.
Please Select a Group Size
Group size is required to show per-person pricing. Your group size can be approximate and can change.