Tuscany is a walker’s paradise. Once out in the countryside, you’ll find no fences except for very few to keep in sheep, and the rare private reserve. The rest—an amalgam of back roads, vineyard paths and cart trails (and some marked footpaths)—make for unlimited freedom to explore and enjoy every ruin, farmhouse, castle, and knoll.
Fascinating walks can be found south of Florence in the more developed Chianti region. But the most dramatic and varied, where every step yields a magnificent view or ancient edifice, is to be found south of Siena, in the UNESCO World Heritage site: The Valley of the Orcia River. I have lived in the western part of the park for over 25 years, yet every day I look around in awe and wonder, and thank whoever created it all, simple farmers and nobility, not to mention the original designer, for having done such a masterpiece. Words are futile here; just go and walk it.
The first 4 items I list—all less than 15 miles— are day hikes. The last one is a small company that organizes tours. You may still go on your own, but they give you the itinerary and have your luggage waiting for you at the next hotel. A word of warning: For the first three walks I laid out, the GPS is not always reliable, so get a compass and print out the maps from the site.
The Chalk Hills (sulle Crete)
From Torrenieri, take the old Cassia turning toward the medieval castle of Cosona. Do a side trip northwest to Lucignano d’Asso, a magical hamlet with a bar where you can eat, drink and be merry. Double back to the Cosona road and head to one of my favorites, the fourteenth-century monastery of Sant’Anna in Camprena. The location is superb, the buildings and gardens charming, and the frescoes by Sodoma worth seeing. Much of The English Patient was filmed here before the cloisters and grounds were restored.
The Brunello Trail
This trail is a good climb of about a thousand feet, through some of the most famous vineyards in the world and you’ll end at the walled town of Montalcino. From Torrenieri, take the road west toward the hill-town that you see a few miles away on the crest. You’ll pass numerous old farmhouses, some abandoned awaiting TLC, others, restored and thriving as wineries.
Gorgeous Castles, Towns and Gorges
Treat yourself and stay overnight at Castello Ripa D’Orcia (very reasonable with good food) and start an unforgettable hike from here. From Ripa D’Orcia, head toward San Quirico. Turn right down to the Orcia River and a travertine bridge that crumbled almost a hundred years ago. Don’t ford the river, turn east to Bagno Vignoni, a truly romantic Roman era hot spring. Indulge in a half hour soak at Hotel della Posta hot pools then have lunch at Leone. Go back to Podere Molino and head along the river to Podere Montelaccio. Swing north toward Ripa d’Orcia and home to the castle.
Isola del Giglio
This sparsely inhabited island, population 1,400, is a place of easy day hikes with breathtaking views, punctuated by good eating. Isola del Giglio (Iris Island) is 10 kilometers from the Tuscan mainland. It is literally zig-zagged by ancient trails—from which every step offers dramatic views—still used by the locals. You can stay in Giglio Castello at 1,000-foot elevation and do day loops: to the east, down to the sea, and the fairy-tale sized Roman port with exceptional seafood; to the west, to wonderful beaches; to the south tip of the island, which is rough and feels like the ends of the earth; or descend to any number of deserted coves along the way. And do try the local wine, Ansonica, grown on tiny, hand-worked terraces—my favorite white. Enjoy.
Walking About Tuscany
This small very personal company has been looking after hikers for 15 years. They can arrange single-day to eight-day tours—you can go either alone or with small groups—with stays in three and four-star hotels in Tuscany’s best regions: San Gimignano, Chianti, Siena, Pienza, Montalcino, etc. You decide on how long of a walk you want since they look after the rest: travel, accommodations, wine tasting, and even cooking classes. Highly recommended.