You'd better suppress the urge to flap your wings and leap from high places—because some of the castles and towers I’m about to name are where only eagles dare to fly. But all are worth every gasp and white knuckle.
Many a Tuscan hilltop offers nearly pristine medieval-landscape views. The region’s silent back roads (most of them ancient mule tracks), wind and dip, ending on rises where I often can’t help but stop, take a deep breath, and just gaze. The lovingly worked fields, vineyards, and olive groves stretched out below—their shapes, curves, textures, and colors—captivate me as much as museum-bound works of art. And where in a museum can you sit before your favorite painting and pull out a loaf of Tuscan bread, some prosciutto, pecorino, and a bottle of wine, and re-live a meal of a thousand years ago?
And then there are the peaks and crags, and sea cliffs. Among my favorites are:
Perched on a rocky outcropping, this early medieval fortress has views of the whole Val d’Orcia (a UNESCO site), plus a winding gorge, castles, hill-towns, and a steaming hot spring used since Etruscan times. At its feet, a charming, ancient town clings to the steep hillside. For the prettiest light, come here in morning.
Sant'Angelo in Colle
In the heart of Brunello country sits this town with its panoramic view. To the north are wild Tuscan woods; to the east, rolling vineyards; to the south, a broad valley with a looming volcanic peak; and to the west, castles, farmhouses, and a glimpse of the blue Tyrrhenian Sea.
This winding medieval hill town is one of the most dramatic seen from any direction—yet the best view is from the very top. Its lovely Piazza Grande is located here; the 360-degree view from atop its municipal tower is the next best thing to seeing Tuscany from a hot-air balloon.
I love this dramatic rocky point that juts into the Tyrrhenian Sea; it’s unique on this coast of long sandy beaches and pine forests. Adjoining the wild Parco D’Uccelina, a vast nature preserve, the town’s fortress offers dramatic views over the azure sea, the coast, and the islands. It’s also got two lovely seafood restaurants.
A wild, romantic place to watch a Tuscan sunset. This tiny town atop limestone cliffs overlooks the spectacular Abbey of Monte Oliveto, and layers of misty hills. The best view is from a blanket in the field below the cemetery. Take a bottle of good wine for an evening you won’t forget.