10 of the Most Beautiful Small Towns in Italy

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Positano

There’s only one thing better than staying in Positano and that’s staying in a hotel with an amazing view of Positano. For it’s only when you look at it from a distance that you get the full perspective of this gem of the Amalfi Coast. Pastel-coloured houses cling to the sides of cliffs tumbling down to a turquoise sea. Wisteria-covered pergolas and colourful blooms punctuate the steep narrow streets, which are lined with smart boutiques and cafés. Here, perhaps more than anywhere else in Italy, the traffic, the parking and the public transport are a nightmare, but even that can’t detract from the magic.

Cortona

It’s not hard to see how Frances Mayes fell in love with Cortona and wrote all about it in her best-selling book, Under The Tuscan Sun. Even on a bleak day, sunflowers add a cheerful note and it’s easy to fall in love with this hilltop town and the bucolic countryside around it. The movie was filmed in and around the town, and the subsequent influx of visitors has brought stylish cafés and galleries. If you get there early in the day, the ambience remains largely unchanged from the lovely old town that stole Mayes’ heart.

Bellagio

The beauty is in all directions from this tiny hamlet on Lake Como. Stretching as far as the eye can see, the lake is surrounded by majestic mountains, with impressive villas and magnificent gardens hugging the water’s edge. Rising up from the dock are narrow streets of stone steps lined with boutiques selling exquisite silk, cashmere and leather. Take a walk to Punta Spartivento, a peaceful spot offering panoramic views of the lake, and the location for many films.

Lucca

One of the gems of Tuscany, Lucca is an old walled city with a round, Roman-style central plaza. It is the birthplace of the composer Puccini and the house where he was born is now a fascinating museum with costumes and original score sheets from his operas. Following a visit to his house you can sit in the sun-drenched square outside the Madame Butterfly Café and enjoy a Campari Spritz. The town is surrounded by 4.2km of walls built during the Middle Ages and since converted into walking tracks and public parkland, providing the perfect setting for a gentle stroll or bike ride.

Ravello

High in the hills above Amalfi, surrounded by woodland with stupendous views of the Mediterranean, is this jewel of a town, celebrated for its exquisite terraced gardens and villas, and its quaint romantic streets. Its beauty has provided inspiration for artists, writers and musicians for centuries, and these days it plays host to a popular summer festival when the whole town is turned over to music – jazz, folk, rock and classical – performed indoors and out, in stunning concert halls and on the streets.

Assisi

Best known as the birthplace of St Francis, founder of the Franciscan Order in the 12th century and patron saint of animals, Assisi has winding streets lined with cute shops and houses built in the local pink limestone. Many are packed to the rafters with religious icons but there are also some great delicatessens and galleries, including Laboratorio Artistico, where the delightful Alice Scaglia paints flowers and landscapes on glass and plexiglass. We couldn’t resist buying some of her work. The basilica housing St Francis’s crypt is a must-visit. The uphill hike to the basilica isn’t over at the front door, as the complex is spread over numerous levels. As our guide, Marco, said: “The road to paradise is steep but the reward is great.”

Spello

Like Assisi, Spello is built from the local pink limestone, so it takes on a gorgeous rosy hue at sunset. Spello has hosted a flower festival since pagan times, and many of the residents take part in an annual competition for the best-decorated houses, so walking around the cobblestone streets is like stepping into a florist shop. The main square is dotted with linden trees that look glorious in autumn, and there are Roman ruins to appeal to the history buffs. We loved the delicatessens and the meal we had at Il Molino, in a 14th century building that was originally an olive oil mill.

Siena

Not far from its arch-rival, Florence, stylish Siena still has a foot firmly in the Middle Ages. The main square, Il Campo, looks much as it did in the 14th century. Not only is it the scene of a colourful horse race twice a year, but the square is still divided into nine quadrants representing different family groups in the town. “The square is the centre of the universe to us; something you don’t find in Florence,” says our guide Nicoletta, in a gentle dig at Siena’s big sibling. Don’t miss the deconsecrated cathedral that looks like a giant wedding cake. Nor can you go past the local specialty, ribollita, a hearty bean soup with crusty bread.

Orvieto

One of the most dramatic locations in Italy, Orvieto rises above almost-vertical cliff faces, offering commanding views of the Umbrian countryside. A labyrinth of caves and tunnels lie beneath the winding cobblestone streets. Dug deep into volcanic rock from Etruscan times right through to the present day, one of the caves houses the quirky Zeppelin restaurant where Lorenzo “The Tuscan Chef” Polegri runs a popular cooking school. The 13th century cathedral is stunning with stripes of black basalt and white travertine. Orvieto is home to Il Gelato di Pasqualetti, some of the best gelato we’ve had in Italy.

San Gimignano

Visit San Gimignano at sunset when the light paints a scene over the Tuscan countryside that you’ll never forget. This walled medieval hill town is impossibly beautiful with a dozen tower houses creating a magical skyline, so unique that UNESCO has declared it a World Heritage site. You could spend days wandering around the shops and piazzas, but we had to be content with half a day – just enough time to buy some of the amazing pastries from Armando e Marcella Pasticceria, and to sample the icecream from world champion gelato maker, Dondoli.

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We visited the beautiful towns of Umbria and Tuscany on Insight Vacations’ Country Roads tour and are grateful to Insight for partially sponsoring our visit. We highly recommend the tour to anyone who wants to experience an obscene amount of beauty in a short space of time, with someone else doing the driving.

Ravello, Positano and Bellagio were visited independently, though we were fortunate to be given a night’s accommodation at the beautiful Casa Angelina, one of the Small Luxury Hotels of the World, from where it is possible to gaze all day on Positano, a view you could never tire of.

Listen to Maurie talking on Travel Writers Radio about our trip to Umbria and Tuscany: