Tuscany Family Bike Tour
Fun & Adventure from Montepulciano to Chianti
Shared adventures shine under the Tuscan sun. Pedal cypress-lined lanes to storybook hill towns, chasing the next gelato stop. Beyond the bike, kids tackle ropes courses and parents sip bold reds. La dolce vita, family style.
We rate our trips based on a range of activity levels from 1-5.
See this trip's Activity Options & Terrain for more details.
From $5,599/person
Saved
Save
Snapshots from the Trip
Trip at a Glance
Highlights
- Explore medieval Montepulciano and ride the iconic Road of the Castles to Radda in Chianti
- Bike through colorful fields of sunflowers in Val di Chiana and the lunar landscapes of the Crete Senesi
- While parents pedal country miles, kids find fun with stand-up paddleboarding, ropes courses and art activities
- Gather around the table at authentic trattorias and classic country villas serving up classic Italian farm-fresh cuisine
- Our Tuscan countryside retreats are the perfect place to swim in the afternoon sun or lounge poolside
Sample itinerary. Trip details may vary by departure.
Start Arezzo Airport & Travel Details
- Bike through the countryside of the Val di Chiana past cypress trees, sunflower fields, grazing sheep and farmhouses
- Tuck into classic Italian dishes 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 vast, sparkling Lake Trasimeno
- Kids share an afternoon of water sports while 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
Luxury Hotel
Set in an 18th-century villa surrounded by gardens, olive groves and vineyards just minutes from Montepulciano, Villa Svetoni has been producing wine on the estate since 1865. Guest rooms pair rustic details such as exposed wood beams, hardwood floors and handwoven rugs with modern, stone-lined bathrooms featuring walk-in showers. (pool)
Hotels may vary on select departures. Click View Dates and choose a departure to see any variations.
- 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 sunset over the countryside from our hotel, an elegantly restored castle-hotel among vineyards and olive orchards.
Night 3
Luxury Hotel
Stunning views of the Tuscan countryside and exceptional hospitality await at this elegantly restored castle-hotel. Leading Hotels of the World property. (pool, spa)
Hotels may vary on select departures. Click View Dates and choose a departure to see any variations.
- Ride along the Strada dei Castelli (Road of the Castles) to Radda and Castellina, 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
- Stroll through the historic trade town of Gaiole, with time to browse the iconic Eroica shop during an evening on your own
- Shop for hand-painted souvenirs and admire Renaissance-style designs at Ceramiche Rampini
- Pause for artisanal gelato in charming historic towns
- Pedal through the heart of Chianti in pursuit of quintessential Tuscan views
- Celebrate a Tuscan family vacation with a memorable dinner at our exclusive hotel.
Nights 4-5
Luxury 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)
Hotels may vary on select departures. Click View Dates and choose a departure to see any variations.
End Florence Airport & Travel Details
This trip has an activity level range of 1-4
Biking routes follow quiet roads through forests, farmland, vineyards and villages. Terrain is hilly, with most days including some longer or steeper climbs to hilltop towns, especially on the long options. Most routes have little car traffic, but entering and exiting larger towns involves stretches with more traffic.
Kid-friendly routes are shorter but hilly, and alternate kids’ activities are available on days with longer rides. Some sections are on roads with traffic, so kids should be comfortable riding with cars and navigating hills.
All breakfasts, 4 dinners, 4 lunches
All accommodations on your Backroads trip
All gratuities at hotels and restaurants
Expertise and services of Backroads Trip Leaders
Kids' bikes, trailer bikes, carriers and kid-sized helmets
Bike fitting and equipment support throughout your trip
Backroads On Trip App with route maps, elevation profiles, daily snapshots and more
Additional local guides and experts, plus equipment for included activities as detailed in your itinerary
Exclusive activities, tours and cultural experiences, as detailed in your itinerary
All luggage transfers and porterage during your trip
Snacks and beverages between meals
Private cocktail and wine receptions on the first and last nights of your trip
Choice of Backroads cycling jersey, t-shirt or hat, plus water bottle and luggage tag
Detailed Travel Planner with destination tips and pre-trip information
