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.
Couples, Friends & Solos
6 days 5 nights
Activity Level: 2-5
Casual & Casual Plus Hotels
From: $3,999 - $4,449 pp dbl occ
($700 for sgl occ)
Bike from one unbelievable view to the next. Marvel at extraordinary Renaissance art and architecture. And savor delicious pecorino cheese, homemade pasta, fruity olive oils and celebrated Chianti and Brunello di Montalcino wines. Few things in this world live up to the hype. We're happy to report that everything you've 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 the region's must-see highlights, including Pienza, a World Heritage site famous for pecorino cheese, exquisite ceramics and Renaissance architecture | After a nourishing spread of Tuscan specialties, ride cypress-lined roads through southern Tuscany's open undulating terrain into the Val d'Orcia | Montepulciano, with its winding streets and hidden squares, invites a stroll | Enjoy post-ride poolside lounging 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)
Climb by bike through a sea of vineyards to the wine village of Montalcino, where enoteche pour samples and remarkable views reach as far as Siena on a clear day | Leave Val d'Orcia behind as you climb up the ridgeline to enter Crete Senesi area, where we reach an agriturismo with farm fresh Tuscan food | Our hotel's terrace provides an idyllic venue for a sunset aperitivo.
An agricultural estate standing on a high ridge between the Chiana Valley and the famed Crete Senesi. (pool)
Engage in a fascinating Q&A session with a renowned local author | Bike past the exposed chalk hills of the Crete Senesi, often depicted in 14th- and 15th-century Florentine and Sienese paintings | Sun-drenched pastures dotted with sheep and crumbling stone farmhouses give way to oak woodland and olive groves | Take some time to explore Siena on your own | Ride rolling hills alongside Chianti Classico and Sangiovese vineyards | Get to know 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.