Travel Guides: Italy Travel Guide: Overview
In Southern Europe—right in the heart of the Mediterranean—lies a boot-shaped country stuffed to the brim with culture, history and fine cuisine.
One or more kids 17+ required (siblings 14+ ok) | Min age to ride e-bike 16+
Family — Older Teens & 20s
6 days 5 nights
Activity Level: 2-5
Casual & Casual Plus Hotels
From: $3,999 pp dbl occ
($700 for sgl occ)
Ride from one unbelievable view to the next. Marvel at extraordinary Renaissance art and architecture. Taste delicious pecorino cheese, homemade pasta, fruity olive oils and tiramisu. Few things in this world live up to the hype. We're happy to report that everything your family has heard about Tuscany is true.
Start Arezzo / End Florence
Start/End locations may vary. Do not book flights until your trip details are confirmed.
Experience some of Tuscany's must-see highlights, including Pienza, a World Heritage site famous for exquisite ceramics, pecorino cheese and Renaissance architecture | Regional specialties provide the perfect fuel for rides on cypress-lined roads | Bike through southern Tuscany's rolling terrain into the Val d'Orcia | Take a family stroll on the winding streets of Montepulciano, pausing for an aperitivo or gelato on one of its hidden squares | Idle poolside at our welcoming hotel.
This enchanting family-owned hotel overlooks the town's central piazza, whose ancient pool is fed by underground thermal springs. (pool, spa)
A sea of vineyards lines our bike route to Montalcino, a wine village where enoteche pour samples and—on a clear day—remarkable views reach as far as Siena | Leave Val d'Orcia behind as you climb up the ridgeline to enter the Crete Senesi area, where we reach an agriturismo with farm fresh Tuscan food | Read or relax and simply take in the scene from our hotel's lovely terrace.
An agricultural estate standing on a high ridge between the Chiana Valley and the famed Crete Senesi. (pool)
Join a renowned local author for a fascinating Q&A session | Ride past the sun-drenched chalk hills of the Crete Senesi, often depicted in 14th- and 15th-century Sienese and Florentine paintings | Sheep-dotted pastures and crumbling stone farmhouses lead to olive groves and oak woodland | Explore magnificent Siena with your family | Bike rolling hills alongside legendary Chianti Classico and Sangiovese vineyards | Discover ridgetop Radda, the center of Chianti wine production | Looking for a gift? Family-owned Ceramiche Rampini offers ceramics hand-painted in the Renaissance tradition.
A tranquil 16th-century villa with wooded grounds, an Italian-style garden and a small church with frescoes by Arcangelo Salimbeni. (pool)
The earlier you book, the more choice you'll have and the lower your price. And you can always change your mind — you won't be charged to transfer to a different trip before your final payment is due. View cancellation policy.
Click on dates for pricing, itinerary variations and to book your trip. Price is per person, double occupancy in USD.
Our Private Trips are best for groups of 6 or more. We suggest joining a scheduled trip.
Group size is required to show per-person pricing. Your group size can be approximate and can change.
Every Backroads trip is designed to appeal to a wide variety of interests and fitness levels. Several routes and a range of levels are offered each day so you can choose how much or how little activity you want to do. Learn more about how we determine activity levels.
The key to a stellar day's ride is a bike that's perfectly in tune with your cycling style… Backroads has you covered with the best bike fleet in the world! Please note that bike requests are subject to availability and prioritized based on the date they're submitted.
Click the arrow to see all bike options.