Tirano is where the Alps run out of snow and start thinking about wine. The town of about eight thousand sits in the Valtellina, the long east-west valley of the Adda, in Lombardy, at the foot of the Bernina Pass, and its mood is distinctly Italian: arcaded streets, warm stone, an espresso at every corner. It is the southern terminus of the Bernina Express, the railway that climbs over the pass from Switzerland, and the station square has red Swiss trains next to Italian ones, a peculiar and pleasing sight.
The town's great monument is the Basilica of the Madonna di Tirano, a Renaissance pilgrimage church built in the early sixteenth century on the spot where the Virgin is said to have appeared in 1504. It is a handsome, spacious building with a great façade, standing at the edge of the town, with a tall bell tower and a square that is almost always full of people. The Valtellina is also a wine country, with steep terraces of Nebbiolo vines, here called Chiavennasca, walled with dry stone and facing south, and the reds that come from them are some of the best in Lombardy. Order a glass with bresaola, the air-dried beef the valley is known for, and a plate of local cheese.
The Bernina Pass road climbs from Tirano on the Italian side in a series of hairpins through the border village of Campocologno, then past the Brusio spiral viaduct, where the railway makes a full circle, and over the pass at about 2,330 metres. The road is wide, smooth and well engineered, with fine views of the Palü glacier and the Bernina range. Switzerland's border posts are manned, so carry your passport or ID.
Fuel, supermarkets and repair shops are all easy in Tirano, and fuel is usually cheaper here than in Switzerland, so use it. Summer can be hot and humid in the valley, while the top of the pass is cold and sometimes foggy. The pass is generally open through the year, though snow can interrupt it in winter. As a place to end a day, Tirano is warm, generous and easy, and a long table outside a trattoria is the right finish.