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.
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Pedal 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.
THIS ITINERARY: 6 days, 5 nights
ACCOMMODATIONS: Casual Plus Hotels
Start Arezzo / End Florence
Start/End locations may vary. Do not book flights until your trip details are confirmed.
Discover some of the region's most celebrated towns, including World Heritage Pienza, famous for pecorino cheese, exquisite ceramics and Renaissance architecture | Savor a spread of Tuscan specialties, then bike cypress-lined roads into the Val d'Orcia through southern Tuscany's open rolling terrain | Take a stroll along winding streets and in hidden squares in Montepulciano.
This enchanting family-owned hotel overlooks the town's central piazza, whose ancient pool is fed by underground thermal springs. (pool, spa)
Bike through a sea of vineyards as you climb to the wine village of Montalcino | Sample wines in charming enoteche and take in remarkable views that—clouds willing—reach as far as Siena | Explore Abbazia di Monte Oliveto Maggiore, the region's most notable monastery, where you can still hear monks praying in Gregorian chant.
An agricultural estate standing on a high ridge between the Chiana Valley and the famed Crete Senesi. (pool)
Meet a renowned local author and engage in a fascinating Q&A session | Ride past the Crete Senesi, the dreamlike chalk hills often depicted in 14th- and 15th-century Florentine and Sienese paintings | Sunny sheep-dotted pastures and crumbling stone farmhouses lead to oak woodland and olive groves | Spend some time to exploring Siena on your own | Bike undulating hills alongside Chianti Classico and Sangiovese vineyards | Check out ridgetop Radda, the center of Chianti wine production | Ready for a few more miles? Pedal all the way to Castellina, a medieval village with an enchanting arcaded passageway | Pick up a souvenir at Ceramiche Rampini, a family-owned shop offering 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.
Every Backroads trip is designed to appeal to a wide variety of interests and fitness levels. We know your pace may vary from one day to the next—and your traveling companion's may differ somewhat from yours. So we present a range of mileage options, and each day you decide exactly what and how much you want to do. LEARN MORE.