Tuscany Wine Country Bike Tour
Cuisine, Culture & Chianti in the Heart of Italy
Tuscany is more than a drop-in destination, it’s a place to take the long way round. Ride along cypress-lined roads with vineyard views around every bend, then unwind with world-class wine, memorable meals and stays in welcoming countryside estates.
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 $6,599 - $7,099/person
Saved
Save
Snapshots from the Trip
Trip at a Glance
Highlights
- Bike our favorite Tuscan roads as we wind our way from the cypress-lined ridges of Chianti to the stark, sculpted hills of the Crete Senesi and beyond
- Wander hilltop towns like San Gimignano and Siena, where medieval skylines and lively piazzas set the scene
- Taste acclaimed regional wines like Chianti Classico and Vernaccia in the very wineries where they’re produced
- Soak up Italy’s old-world Renaissance beauty in the historic villages of Radda and Gaiole in Chianti
- Unwind at handpicked hotels that capture the best of Tuscany, from an elegantly restored 12th-century castle to a serene hilltop estate
Sample itinerary. Trip details may vary by departure.
Start Arezzo Airport & Travel Details
- Embark on a quintessential Tuscan adventure, riding scenic routes in the Chianti Classico wine region
- Spin through the rolling countryside and take in the sweeping vistas—you’ll soon realize why this is one of the most famous regions in the world
- Sample local specialties at an organic agriturismo before biking past olive orchards and vineyards
- Take time to relax at our hotel, a countryside manor home with an outdoor pool and extensive wellness facilities
- Ride into the heart of Chianti, passing through legendary wine villages like Gaiole and Castelnuovo Berardenga
- Cycle through the Crete Senesi, an area known for its lunar landscape
- Explore Siena’s medieval back streets and grand Piazza del Campo, home to Italy’s most important horse race, Il Palio
- Learn the nuances of Tuscany’s renowned red wines at an exclusive sommelier-led tasting.
Nights 1-3
Luxury Hotel
Set on a hilltop in the Chianti countryside near Castelnuovo Berardenga, Hotel Le Fontanelle is a restored estate surrounded by vineyards and rolling Tuscan hills. Elegant rooms and common spaces reflect classic Tuscan style, while landscaped gardens, an outdoor pool and a spa offer inviting places to relax. (pool, spa)
Hotels may vary on select departures. Click View Dates and choose a departure to see any variations.
- Ride the ridge to ancient hilltop Radda, former capital of the Antica Lega del Chianti (Old Chianti League)
- Visit the picturesque neighboring village of Castellina
- Settle into our hotel, a restored 12th-century castle surrounded by vineyards and olive groves, making the most of its thermal pools and spa
- Celebrate in Tuscan style over dinner
- Bike to Colli Fiorentini, northern Tuscany’s slice of Chianti wine production
- Follow cycling routes in the verdant Elsa River Valley to the spectacular World Heritage town of San Gimignano, crowned by 13 towers
- Toast la dolce vita with a glass of refreshing Vernaccia, Tuscany’s most famous white wine, before heading to Florence.
Nights 4-5
Luxury Hotel
Set on a hilltop in the Colli Fiorentini countryside near Tavarnelle Val di Pesa, COMO Castello Del Nero occupies a restored 12th-century castle surrounded by vineyards and olive groves. Historic frescoes and vaulted interiors reflect the estate's long history, while contemporary design brings a refined modern touch. Expansive gardens, a pool and a full-service spa create a serene atmosphere. One Michelin Key; Condé Nast Traveler Readers' Choice Award (pool, spa)
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 2-4
All breakfasts, 4 lunches, 4 dinners
All accommodations on your Backroads trip
All gratuities at hotels and restaurants
Expertise and services of Backroads Trip Leaders
Fully equipped Backroads titanium bike, Wahoo GPS device, helmet and accessories
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
