Start your explorations at hilltop Piazza Grande (to avoid the climb, take the free elevator at the junction of Via Repubblica and Via Baldassini, which runs daily 7:45am–7pm). After marveling at the airy view over the valley below, turn around to admire the rambling Palazzo Ranghiasci behind you, on the north side. That the facade resembles an 18th-century neoclassical British country house is no accident: A nobleman of the time married an English lady and brought her back to Gubbio, where she languished in homesickness before fleeing. To lure his wife back, the heartbroken duke commissioned an architect to rebuild the front of his palace in the latest British fashion, but to no avail—his bride never returned. Note that one of the Greek-style columns has been clumsily replaced with bricks—it needed patching after the Allies lobbed a shell into the piazza to dislodge Nazi occupiers at the end of World War II. Next head for the Fountain of the Madmen in Largo Bargello, a short walk west of the piazza along Via Consoli, but approach with care—it’s said that if you circle the monument three times you are sure to go mad.
Steep, narrow lanes switchback up the hill to Gubbio’s sturdy Duomo and fortresslike Palazzo Ducale at the top of the town, where church and state could keep an eye on the citizens below. (In 1472 Duke Frederico da Montefeltro commissioned for his palace the Gubbio Studiolo, a glorious room decorated with wood inlay; to see this treasure nowadays, however, you’d have to go to the Metropolitan Museum of Art in New York City.) As you approach the ducal palace on Via Federico da Montefeltro, through a gate you’ll see the Botte dei Canonici (Canon’s Barrel), a humongous vessel capable of holding more than 5,000 gallons of wine. Monks in the monastery above, or so the story goes, could serve themselves by dipping a ladle through a trapdoor in the ceiling.
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