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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Discover the joys of the Tuscan table as you learn the secrets of Italian cooking from our charming local friends. Celebrate fresh seasonal ingredients prepared with passion, yet minimal manipulation. Slow down and let food be the focal point of the day. And savor this journey that nurtures both body and spirit.
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.
Meander through vineyards, woodland and Renaissance hill towns | Get a taste of the region’s undulating terrain as you walk from Castellina to Vèscine | Homer once called olive oil “liquid gold”—you’ll call it “delicious” during our exclusive degustazione (tasting) | Explore Panzano, home to numerous fine Chianti wineries | High ridges and peaceful forests lead the way to our lunch spot in the home of a local friend—a one-of-a-kind experience! | Join pizzaiolo and Backroads’ friend Mario to learn how to let the pizza dough fly.
A 13th-century hamlet handsomely restored as a welcoming hotel with unsurpassed views of the Tuscan countryside. (pool)
From the tiny hamlet of Vertine, hike from one unbelievable vista to the next, stopping for lunch at a local home for an alfresco feast among the grapevines | In Radda, enjoy a private wine talk and pour—and balsamic vinegar tasting—with our friend Fabrizio | Prepare a home-style Italian meal alongside locals in the cucina of their cooking school.
Located in the heart of the Chianti region, this elegant 14th-century manor house features spacious guest rooms with original frescoes. (pool, spa)
Follow the strade bianche (white roads) of southern Tuscany’s Val d’Orcia | Head south to the crete senesi (chalk hills) to hunt for truffles | Wander in Renaissance-style Pienza, Pope Pius II’s utopian village | Lunch takes place at an agriturismo (working farm) and dinner is a hands-on affair as we prepare piatti tipici, typical Tuscan dishes | Say arrivederci to Tuscany with a leisurely hike in the countryside surrounding Bagno Vignoni.
This enchanting family-owned hotel overlooks the town's central piazza, whose ancient pool is fed by underground thermal springs. (pool, spa)
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.
Note: The terrain on this trip includes a mix of rolling vineyard paths, gravel roads and wooded trails.