The Italy Detour

Bologna, under the porticoes

Bologna doesn't try very hard to be photogenic in the way Florence does, and that's part of its charm. It's a working university city, home to the oldest university in the Western world, with over sixty kilometers of covered arcades, the porticoes, running through the historic center. You can walk most of the old town in the rain and barely get wet.

It's also, by wide agreement among Italians themselves, one of the best food cities in the country, the birthplace of the ragu that gets flattened into 'bolognese' abroad, along with tortellini, mortadella and a produce market culture that's kept much of its old character.

Give it at least a day and a half, more if you want to actually eat your way through it properly.

San Marino, a country on a mountain

From Bologna, head toward the Adriatic coast and up into San Marino, one of the world's oldest surviving republics and, oddly, one of the smallest countries anywhere. The old town sits on the slopes and summit of Monte Titano, with three medieval towers strung along the ridge, and on a clear day the view stretches out over the Adriatic in one direction and the hills of Emilia-Romagna and Marche in the other.

It's touristy in the center, full of shops selling duty-free goods and souvenir crossbows, but climb up past the main square to the towers themselves and the crowds thin out fast, and the views alone justify the detour.

• Reachable by bus from Rimini, which itself connects by train from Bologna
• No passport stamp or border formality, San Marino has open borders with Italy
• Wear real shoes, the paths between towers involve genuine climbing
• A half day is enough unless you want a long lunch with the view

Urbino, a Renaissance court on a hilltop

Urbino is smaller and steeper than most Italian hill towns, built around the Palazzo Ducale, the palace of Duke Federico da Montefeltro, whose court was one of the great centers of Renaissance humanism in the 15th century. The palace itself, with its studiolo covered in intricate inlaid wood panels, is one of the most quietly extraordinary rooms in Italy, and it rarely has the queues of anything comparable in Florence.

The town is also still a working university city, which keeps it from feeling like a museum piece, students fill the bars and steep stairways well into the evening.

Perugia and Orvieto, Umbria's twin hill towns

Moving south into Umbria, Perugia is bigger and livelier, a university town with a striking main square and, each summer, one of Europe's best known jazz festivals. Orvieto is smaller and quieter, built on a plateau of volcanic rock, with a cathedral facade so ornate it's genuinely startling the first time you see it up close, and an underground network of caves and tunnels carved beneath the town over more than two thousand years.

Both connect reasonably well by regional train to the rest of the route, and either makes a good final stop before heading on to Rome or Florence if that's the next leg of a longer trip.

How to sequence it

The honest logistics: Bologna to Rimini is an easy train, Rimini to San Marino is a short bus, but San Marino to Urbino and onward into Umbria works better with a rented car or patience with regional buses, since train coverage thins out considerably in this part of central Italy. If driving isn't an option, it's still doable, just build in extra time for connections and don't expect the frequency you get on the main north-south lines.