Italy’s Most Charming Small Towns

 Most tourists in Italy flock to the country’s major attractions and cities, paying homage to the wonders of Rome, Florence and Venice. They are, of course, must-see destinations. But once the major cities have been explored, travelers should take the less traveled path to discover Italy’s tiny towns, dotting mountainsides and valleys. Here, we’ve picked our 5 favorite charming small towns in Italy.

1. Ravenna

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Visitors to Ravenna will be hard-pressed to decide which of the town’s extraordinary sights to explore — the 8 UNESCO World Heritage sites or the museums? Dante’s tomb or the 4th- century churches? Despite the number of attractions, you’ll want to spend your time first and foremost appreciating the mosaics. Ravenna’s claim to cultural fame may well lie in the glimmering Christian and Byzantine mosaics found throughout the city, which are considered the finest outside of Istanbul.

To experience some of the oldest and finest examples of Ravenna’s mosaics, explore the Mausoleo di Galla Placidia, admire the domes of Battistero degli Ortodossi and Battistero degli Ariani, and marvel at the Chapel of Sant’Andrea’s mosaics depicting flowers, figures of Christ and at least 99 bird species. To experience as many of Ravenna’s mosaics as possible, purchase a combined ticket to the town’s sites, admission to 6 monuments. Be sure to pay a visit to Dante’s tomb; the Italian literary giant called Ravenna home for 20 years, and wrote his epic, Divine Comedy while here.

2. Urbino

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One of Italy’s most romantic hill towns, Urbino lies tucked in Italy’s Le Marche region, an off-the-beaten path nook filled with stunning views of the Apennine Mountains along with rich Renaissance culture. Urbino, the Marche region’s capital, might well be the most charming of its towns, though most tourists merely know it as the town ruled by the Duke of Urbino, whose famed profile portrait by Piero della Francesca hangs regally in the Uffizi. In the 15th century, the duke served as a great patron and helped foster one of Italy’s most vibrant arts scenes, as well as a still-revered university.

Urbino’s Ducal Palace houses one of the nation’s most illustrious Renaissance art collections, and the entire town has been named a UNESCO World Heritage Site. Spend time mingling with the students who relentlessly converge in the Urbino’s Piazza della Repubblica and grab an espresso at Caffè Basili, before exploring the 17th-century Duomo and the Renaissance painter Raphael’s house (now a museum). Next, trek to Albornoz Fortress at the top of Urbino to capture photos of the postcard-perfect town sprawling below.

3. Lecce

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“The Florence of the South,” as it’s sometimes called, Lecce steals the hearts of travelers who, upon arriving, find themselves immersed in the town’s flowery barocco leccese, an ornate style of architecture. Many of Lecce’s buildings and monuments date back to the city’s heyday, between the 16th and 18th centuries, and were constructed using this region of southern Italy’s soft sandstone, which could be carved into swirling columns and even gremlins. Spend your time meandering through the tiny town’s ancient quarter, sipping an aperitivo at a bar overlooking the 12th-century square, followed by window-shopping along the Via Vittorio Emanuele.

Explore the ruins of the town’s Roman Amphitheater; built in the 2nd century, it could once accommodate some 25,000 people. Then pop into the church of Santa Chiara to admire its ceiling’s papier-mache decorations. You won’t suffer a shortage of delicious restaurants in Lecce, but do stop by Casareccia. Located a bit beyond the center of town, the restaurant offers mind-bogglingly tasty, traditional, local cuisine including — brace yourself — horse.

4. Ravello

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As you ascend the Amalfi Coast’s precipitous cliffs while riding in a bus taking hairpin curves (without braking!), you might find yourself wondering why, exactly, you decided to make the trip up to the tiny town of Ravello. Then, as you arrive in town, breathe in the crisp sea air, and gaze down at the extraordinary coastline twisting below, you will know: Ravello is the Amalfi Coast’s hidden gem.

Plan to tour the town’s 2 major villas, Villa Rufolo and Villa Cimbrone, if for no other reason than to catch a glimpse at how the international jet set used to live while furiously snapping panoramic views from their many terraces and gardens. It’s even possible — if pricey — to spend a night in Villa Cimbrone, and dine at its tiny restaurant. While the villas are undoubtedly the major attractions here, follow them with a visit to the Duomo; an 11th-century cathedral noted for its bronze door. Check out the relic here of St. Pantaleon; his blood sits in a vial, which, on the anniversary of his death (July 27), is said to mysteriously liquify.

5. Gubbio

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Plan ahead and save plenty of suitcase room for souvenirs before you visit Gubbio, the town in Italy’s Le Marche region that is widely considered the ceramics capital of Italy: Visitors can scoop up all the hand-painted pitchers, vases and plates that their hearts desire. It’s hard to over-romanticize Gubbio; the town stretches up a mountain, with winding medieval streets, arching buttresses overhead supporting centuries-old buildings and flower boxes dangling from most windows and dripping with geraniums (in season, of course).

Take the chairlift to the 16th-century Basilica of St. Ubaldo (named in honor of the town’s patron saint), where you can actually see his desiccated body preserved above the altar in a glass casket. Visit the minimalist Piazza Grande, admiring the views of the valley beyond, then head into the Palazzo dei Consoli and museum on the piazza’s edge, and take a peek at the 7 bronze Eugubine Tables, a set of tablets inscribed with the most complete version of the Umbrian language. Other notable sites include the Teatro Romano, the remains of a Roman amphitheater, and the 13th-century Sant’Agostino church, which contains the fresco “The Life of St. Augustine.”

Gabicce Mare, Italy: Secret Seaside

Italy’s Adriatic coast is, on the whole, a very local place: a summer playground for Italian families. Ranks of colour-coded umbrellas mark the progression from one beach “concession” to another along interminable stretches of flat white sand; nondescript developments of high-rise hotels occupy the flat shoreline, overlooked by more ancient towns in the hillier hinterland.

Gabicce Mare is a delightful exception to this rule. To the west, it melds into the northern Adriatic beach resorts, separated only by the canal that marks the border between the Marche region, and neighbouring Emilia Romagna. But rocky heights descending to the coast to the east link Gabicce to the wilder, more rugged area of Gabicce Monte and the Monte San Bartolo nature reserve (www.parcosanbartolo.it). Intrepid visitors wanting more remote sands away from the beach umbrellas, can trek to secluded coves below the nearby hamlets of Fiorenzuola di Focara and Casteldimezzo: it’s an abrupt switch from order to wilderness.

At Gabicce Mare itself, the sweep of white sand widens from east to west — from woodland to canal. Breakwaters keep any rough sea off the strand where stabilimenti (essentially, beach cafés) and hotels arrange umbrellas and deckchairs in neat, brightly coloured rows. It’s the way Italians do the beach: a daily or weekly rate will get you some shade, somewhere to lounge and the right to use the establishment’s bathroom and shower facilities; if you’re staying in a beach-side hotel, this will probably be included in the package. On the sand between seats and briny, children desport themselves, teenagers preen over beach volley moves and parents stroll and chat.

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At lunchtime, the mouthwatering smell of fritto misto (fried mixed seafood) and spaghetti ai frutti di mare (spaghetti with shellfish) wafts from the cafés lining the shore, over the sand and out towards a (very un-Italian) pier which these days is looking rather forlorn, waiting for redevelopment.

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The scene here in high season is for those who like their beach peopled and pulsing. North-westwards along the coast, the pulse quickens still further in Riccione and Rimini, which are club-culture meccas. Committed party-ers can take a train at Cattolica-Gabicce station for the short hop to Riccione; if you don’t dance the night through until the first train back at around 6am, you can always walk the six-odd kilometres.

It’s a very different scene in the opposite direction, where wooded hills climb swiftly towards the Monte San Bartolo nature reserve. (A shuttle service between Gabicce Mare and Monte spares you a hot hike.) Here out-of-time walled villages — fortified against pirate attacks — retain a distinctly Medieval air, and sandstone cliffs plunge seawards from a high coastal plain where farmers work their fields between thick woods of poplar and downy oak punctuated by splashes of orange-flowered pomegrate and sweetly perfumed gorse. The occasional path (the one from Fiorenzuola is perhaps the best) wends its way down towards narrow, pebbly coves: in low season, you may find you have these to yourselves, give or take a lone wanderer or two, picking through driftwood or examining the sea-sculpted stones known as cogoli in the local dialect; in season, you’ll have to share, though only with people hardy enough to brave the 20-minute slog (bring water) — or those with boats who pull into the bays.

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In the park’s higher reaches, dense woods shade tracks that are perfect for exploration on foot or bike. Trek & Bike Experience (www.trekmtb.it) organise tours and rent bikes; their Bike & Boat package (35 euros) takes you in one direction on road or mountain bike, and back by boat, spotting falcons’ nests and improbable cliff-clinging vegetation.

Getting there

Ryanair and Easyjet both offer flights to Bologna (130km); Ryanair also flies to Ancona (70km). There are regular train services from Bologna (from 10.70 euros) and Ancona (from 5.60 euros) to Cattolica-S.Giovanni-Gabicce.

Where to stay

In stunning countryside slightly back from the coast, Castello di Granarolo is a chic architect-designed castle reconstruction, with nine self-catering units around a stylish pool area. Weekly high-season rent from 1,120 euros (sleeps two) to 2,190 euros (sleeps four); +39 0541 969970; www.castellodigranarola.it.

For the full beach experience, three-star La Rotonda sul Mare is literally on the sand. Airy white rooms have vintage marine touches; the Luna suite comes with a private terrace and jacuzzi. There’s a restaurant too. From 33 to 70 euros per person per night B&B ; +39 0541 954572; www.larotondasulmare.it.

High on the hill in Gabicce Monte, the four-star Hotel Posillipo has superb sea views. There’s a pool up here, and a shuttle bus for easy access to the beach. Double rooms from 140 euros B&B ; +39 0541 953373; www.hotelposillipo.com.

Where to eat

Gelaterita (via C. Battisti 56, Gabicce Mare) is a great place to cool down with an excellent lemon sorbet, or one of many creamy flavours of ice cream made in-house.

Telodiro Lounge Bar (lungomare C. Colombo, +39 339 6536621, www.telodirobeach.com) is an all-day beach-side café, serving breakfast and light lunches. But it’s as a cool evening aperitivo hang-out that it comes into its own, with craft beers and cocktails.

Heading uphill towards Gabicce Monte, Osteria del Sorriso (piazza Valbruna 3; +39 0541 963833) has good fish and superb views across the beach below.

The inside track

Back from the coast, the Marche region is a little-visited area of spectacular, unspoilt countryside. Just 30km to the south, the walled city of Urbino — a Unesco World Heritage site — was a centre of art and learning in the Renaissance. Its Palazzo Ducale houses works by Titian, Raphael and Piero della Francesca.

The top 10 villa holidays in Italy

1. Podere Palazzo, Lazio

Tuscany, Umbria and Lazio meet in a landscape of wild beauty, where boars and porcupines roam free in the Monte Rufeno regional park and views stretch for miles towards lofty Monte Amiata. Just inside Lazio, this stylish five-bedroom villa was renovated by the Chicago-based Italian architect Patrizio Fradiani in 2007. It’s a well-judged mix of old and new, with tasteful modern furnishings and fittings playing off against the terracotta floors, wooden beams and old stone walls. The heated infinity pool has stunning views – and there’s an organic vegetable garden as well as olive and fruit orchard tenants are welcome to raid for dinner. Nearby are the hot springs of San Casciano dei Bagni, while the village of Trevinano – which can be seen across the valley – has two great restaurants, one (La Parolina) a fancy Michelin-starred place, the other (Gianfranco) a good downhome trattoria.

This villa has a heated infinity pool with fantastic views

From £3,100 (00 1 773 425 5730; poderepalazzo.com). Lee Marshall

2. Historic Syracuse

There are plenty of luxury villas within driving distance of Siracusa (Syracuse), but for couples or small family groups who want to combine culture with la dolce vita and can live without a pool, the award-winning rental company Think Sicily has two delightful sea-view apartments inside Ortigia, the historic city’s once-shabby but now increasingly chic centro storico. There’s not much to choose between the properties, Archimede and Ortigia: both feature stylish décor and spacious roof terraces with endless views out across the Ionian Sea.

From £1,887 Archimede (sleeps six); from £2,240 Ortigia (sleeps six) (020 7377 8518; thethinkingtraveller.com). LM

3. Borgo di Vagli, Tuscany

Not so much a villa as a village, Borgo di Vagli is a hamlet of 14th-century houses, expertly renovated but gloriously lost in time. Just getting there will help you shake off the 21st century – quite literally, as the bumpy final 2km of unpaved approach road are a serious challenge. In this hilltop fastness the internet seems an anachronism, with wooded mountains as far as the eye can see: in the restaurant kitchen, the cook is floury to her elbows, while the vegetable garden yields wonderful produce for the table. But a landscaped terrace has two pools for sun-worshipping, and the rustic simplicity of the 21 self-catering houses conceals a wealth of up-to-the minute facilities. For guests who can handle the road, pretty Cortona is nearby, and the historic towns of Tuscany and Umbria are conveniently close.

From £805 through Traditional Tuscany (0800 975 5379; traditionaltuscany.co.uk). LM

4. Villa Levanto, Liguria

On the western edge of the Cinque Terre – that string of near-vertical Ligurian villages beloved of walkers – Levanto is a characterful, cultured seaside town with a long sandy beach. It’s perfect for families keen to combine gentle coastal walks – made more accessible thanks to frequent, cheap trains that link the town with all five Cinque Terre villages – with some bucket-and-spade time for the kids. Up above the town, but only a 15-minute walk from the beach, pretty, ochre-washed Villa Levanto would work well for a group of friends or two medium-sized family groups. Think of it as a country villa near the beach.

Between June and September, weekly rental varies From £4,550 through Bridgewater’s Idyllic Italy (0161 787 8587; bridgewatertravel.co.uk). LM

5. Villa La Quiete, Lake Como

For a once-in-a-lifetime holiday, you could do worse than this magnificent 18th-century villa in Tremezzo on the western shore of Lake Como, frescoed and stuccoed to the hilt and surrounded by formal gardens that descend to your own private landing stage. Once owned by Duke Gian Galeazzo Serbelloni, an Italian supporter of Napoleon, the villa is a living museum, with trompe-l’oeil artworks by two pupils of Tiepolo and a historic weaponry collection among its many treasures. There are six luminous double bedrooms done out with true antique noblesse oblige. And if the rental seems steep, bear in mind that it includes your own private butler and chef. It makes George Clooney’s place down the road look positively shabby.

From £19,000 through Bellini Travel (020 7602 7602; bellinitravel.com). LM

6. DIY Marche

Monastero di Favari is a restored 17th-century monastery

Sometimes it’s worth looking beyond the villa rental companies – especially in areas like Le Marche, which are patchily covered by most of the usual Italy specialists. Cut-out-the-middleman websites like Owners Direct (ownersdirect.co.uk) and Airbnb (airbnb.com) offer a degree of anti-scam protection and allow you to check out reviews left by previous tenants. Among the well-liked Owners Direct properties in Le Marche is the Monastero di Favari (search for “Villa in Apiro”) – a sensitively restored 17th-century monastery, owned by an Anglo-Italian couple, that sleeps up to 15. On Airbnb, home in on the area just to the north of Urbino and among the first results you’ll see a lovely old farmhouse near the village of Mondaino, which sleeps seven, restored and decorated in romantic bohemian style by an English artist couple, Phelan and Susan Harlock-Black.

Monastero di Favari from £1,740; Mondaino from £475, including Airbnb service fee. LM

7. Palazzo dei Leoni, Lake Orta

Less well known than Como or Maggiore, Lake Orta is a mysterious place, of contemplative hamlets and mists that shroud picturesque San Giulio island. Set in the village of Vacciago, the recently renovated eight-bed Palazzo dei Leoni is a historic townhouse where decorated coffered ceilings and antique marble fireplaces blend with a minimalist design pared back though anything but neutral. From its pretty garden-courtyard, complete with dining area, through its sleek kitchen to its top-floor bedrooms with superb lake views, this is an exceptionally sophisticated village retreat.

From £3,640 (00 39 335 571 6654; palazzodeileoni.it). LM

8. Villa Dolce Vita, Venice

When you’ve explored all Venice’s alleyways and sampled its plush hotels, where do you go next? Out into the hugely atmospheric lagoon is one option, and to savour it to the full, a holiday home in a watery setting is essential. The owner-renter site HomeAway offers an intriguing selection. Facing Venice-wards near Treporti, the four-person Villa Dolce Vita is a stylish contemporary makeover of an old casone – a rural estate house used for fishing and hunting trips. As well as high-tech gadgetry, a salt-water swimming lake and manicured lawns running down to the water, it has its own mooring stage. Larger still – sleeping 15 – is the Villa San Giovanni, on a private island off Torcello; there’s a pool, extensive gardens, a cook and a private boat service.


The garden and pool of Villa San Giovanni

Villa Dolce Vita from £320 per night; Villa San Giovanni from £962 per night (homeaway.co.uk). LM

9. Golfo di Orosei, Sardinia

On Sardinia’s mountainous east coast, some 90km south of Olbia, the Golfo di Orosei has an appealing mix of craggy cliffs and pine-shaded beaches. With no major town on this stretch of coast, there is instead a sprinkling of low-key resorts well-placed for some of the island’s best swimming. Most places are within reach of the inland centre of Orosei, an atmospheric old town of grey and black basalt interwoven by a medieval skein of alleys dotted with handsome churches and palazzi, not to mention some excellent and reasonably priced restaurants. HomeAway has a selection of properties to rent on the coast, including Casa Siccas, a modern, spacious, recently renovated two-bedroom apartment with a terrace, 50 metres from the sea at Località Sas Linnas Siccas.

From £840 (homeaway.co.uk). Rob Andrews

10. Casa del Conte, Umbria

Umbria has no shortage of pretty pastoral countryside, so the key to a villa holiday is to find a location that is also convenient for exploring the region’s dozen or more hill towns. The Italian specialist Real Holidays has a small but well-chosen selection of properties close to several towns, including some apartment and agriturismo options. A favourite is Casa del Conte, a five-bedoom house with private pool (and ruined medieval tower), sleeping up to 10, that dates back to the 17th century. It is in a pretty rural setting, overlooking the Tiber Valley, but just 10 minutes’ drive from Todi, one of the most compelling of the region’s smaller towns. If you visit in the last 10 days of August, look out for the acclaimed Todi Festival (todifestival.it), a wide-ranging arts event that celebrates its 29th year in 2015.

From £4,075 (020 7359 3938; realholidays.co.uk). Tim Jepson