Four inspiring Italian itineraries

Eloise Barker

Photography by Noppasin Wongchum / Getty Images

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Take yourself on a grand tour of the classical marvels of Italy and get devastatingly distracted on the way. The gelato is silk-soft in Rome, the trattorias are tempting in Tuscany, and, in Sorrento, life hands you lemons. Read up on our fabulous fly-drives.

Rome – Tuscany – Pisa

Best for… Classical ruins, ancient hill towns and a glass of Chianti

The journey: 221 miles


Start your tour in lazy old Rome, where classical sites are high on the agenda. After strolling the ruins of the Roman Forum, avoid the gladiators at the Colosseum and instead tackle massive portions of gelato – try unusual flavours like lavender and pear. The famous Pantheon looks uncompromisingly squat on the outside but has a perfectly proportioned domed ceiling within, a true architectural marvel. At the top of Aventine hill, look through a keyhole in a gate for a special, secret view of Saint Peter’s Basilica down an avenue of trees. Pre-dinner drinks are best served in the quieter Trastevere neighbourhood.

Where to stay:

The Inn at the Spanish Steps is a small luxury hotel spread over four buildings. All the rooms are colourful and chic. To kill the mood, pop into the house nearby where the Romantic Poet John Keats died of tuberculosis. If you want a stylish room, The First Luxury Art Hotel Roma is a boutique hotel that feels like the apartment of your cool, rich friend. Right near the grounds of the Villa Borghese, it’s topped with a gorgeous rooftop terrace. Wake up early the next day to get in the queue for the Vatican. Don’t forget to look out for Da Vincis and Caravaggios in the Vatican Galleries on your way to the Sistine Chapel.

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If Amalfi were a colour it would be yellow – for its lemon groves, colourful facades and local Limoncello.

  • Delicious gelato ice cream in front of the Pantheon, Rome. ©Uğur Keskin.

    Ice and sights

    You might admire your cone of ice cream more, but the Pantheon is still the largest unsupported dome in the world, 1,300 years after its construction. On April 21 every year, light shines through the Oculus and creates an optical effect in front.

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  • Tuscany’s rolling hills. ©StevanZZ.

    As far as the eye can see

    The colours of Tuscany shift with every season. Roam this beautiful region from village to village. Book return flights to Pisa.

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  • Inside the San Lino Church, Volterra Italy. ©I just try to tell my emotions and take you around the world.

    Tour of the town

    Volterra is an ancient UNESCO sight with an atmospheric old church filled with art by Tuscan masters, a museum of Eutruscan tombs…and, to its profound embarrassment, it’s also where they filmed certain sensationalist scenes from teen film franchise, Twilight.

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Tuscany is a purple haze of hills. Long driveways of poplars lead to old wine estates and traditional village life prevails. Drive from hilltop town to hilltop town like an invading army. Visit San Gimignano or Siena’s remarkable green and white cathedral, which resembles a marble Battenberg cake. Look out for regional churches with altarpieces painted by Tuscan masters. Cycle round the walls of wonderful Lucca and climb its tree-topped tower. For a bit of quiet, visit distant Volterra with its Etruscan relics.

The beautiful city of Florence isn’t far away for a visit – it’s famously the seat of the barbaric Medici family, the home of the Uffizi and some of the greatest artworks in the world, including Botticelli’s Birth of Venus. Once you’ve climbed the Duomo and admired the bronze relief work on the baptistry, cross the river into the Boboli gardens or savour the silence in Fra Angelico’s convent.

Where to stay:

Sitting pretty with views over the surrounding Tuscan countryside, Castello del Nero is a twelfth century castle with delicate frescos, wooden rafters and a sweeping gravel drive. Feel like landed Tuscan gentry eating piglet at the Michelin-worthy restaurant. Unlike the old gentry, you can also enjoy the modern spa, an outdoor pool and a spot of tennis.


After Florence, it’s easy to pop to Pisa to end your stay. This gritty city is worth visiting for its elegant Cathedral Square, site of the infamous freestanding bell tower with its unintended 4-degree lean. It’s smaller than you might have expected, and exquisite, shining white. Climb its glistening marble steps for a strange, tilted experience. The Germans used it as an observation tower in the Second World War.

Where to stay:

Grand Hotel Bonanno is a comfortable four-star hotel just ten minute’s walk from the tower and five minute’s from the train station. A tasty and varied continental breakfast is included with your room.

  • A statue in Pompeii. ©sestovic.

    Ancient wonder

    A day trip to Pompeii will hit home – what was once a Roman town is now a museum and graveyard all at once. Whilst the eruption in 70 AD of Vesuvius managed to preserve houses, murals and artwork for the world to see, it also wiped out an entire population.

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  • Galleria Vittorio Emanuele at Piazza del Duomo Milan. ©Mlenny.

    Milan’s living room

    Since its opening in 1877, the world’s oldest shopping arcade has been a meeting place for classy shoppers. Book return flights to Milan.

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  • Juliet’s balcony in Verona. ©druvo.

    Did you know…

    Though Shakespeare set three of his plays in the Verona, there’s no evidence that he ever travelled here. Don’t let that stop you visiting. Verona has a pretty and lively town centre set around lovely piazzas, and plenty of historic sights.

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Milan – Lake Como

Best for… The fashion set

The journey: 53 miles


If Rome is hot and lazy, then Milan is cool and industrious. Outside of its bi-annual fashion shows you will always spot Salvatore Ferragamo-shod socialites pounding the streets. For other kinds of street style, Milan’s cathedral is essential viewing. This gothic gateau took six centuries to complete, has a spiky facade, and you can access the roof free of charge. The inspiration for countless cantos, it’s both beautiful and overbearingly detailed.

Historical shopping centre Galleria Vittorio Emanuele II, with its airy arcades, is great for hitting up expensive Italian brands like Prada’s original flagship, which opened in 1913. You can also browse stylish (and expensive) design icons in the airy lifestyle shop, 10 Corso Como.

Sforza castle is right in the heart of the city and has glimpses of Da Vinci murals in dire need of repair and an unusual Michelangelo statue, left unfinished. For a Da Vinci in a better state, seek out a ticket for The Last Supper – here it’s Il Cerancolo. You have to book, sometimes months in advance. The mural is housed in a church a little way out of the centre of town. 

Panzerotti is the street food of choice in Milan – that’s a small, cheese calzone that’s great for a filling snack. Eat it in the Brera district, as you skirt fortune tellers to find the perfect evening spot.

Where to stay:

Lagare Hotel Milano-Mgallery Collection is a sleek hotel in a modern area of the city. The covered rooftop bar offers city views and DJ nights. Or try Chateau Monfort, a five-star luxury hotel. Grand and imposing, with a great stone entrance, it has gorgeous colour schemes and even a Cinderella-themed bedroom with pumpkin cushions.

Lake Como

Pick up your car and drive down to Lake Como, just 50 miles from Milan. This beautiful lake, described by Shelley as like a ‘mighty river’, snakes along a shore lined with posh villas and holiday homes.

Don’t forget to drop into a bar for apertivo. Between the hours of seven and nine, food is included with your drinks – pizza bread, bruschetta, mini cocktail sausages… the quality depends on the establishment.

Where to stay:

Grand Hotel Tremezzo is filled with special delights, not least its neighbour, a palatial historic villa, a floating pool in the lake with its own champagne bar and plush velvet furnishings. Be sure to pop into the nearby Villa Carlotta’s botanical gardens, full of mature azaleas and tip-top trimmed topiary.

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Venice – Verona – Lake Garda

Best for… Romance on a grand scale

The journey: 75 miles


Ahh – Venice. This beautiful, sinking city is riddled with canals and arched bridges. Get lost in its flooded back alleys and breathe a sigh of relief when you find the brightly lit St Mark’s Square on the edge of the sparkling lagoon. You can wander the city in a couple of days, enjoying installations from the summer Biennale art festival. Seek out the chic and compact Peggy Guggenheim museum in Dorsoduro, which has a charming Yoko Ono wish tree in its little sculpture garden. The ghostly spirit of Venice comes to life in the annual carnival masquerades, but outside of carnival season, eat tasty baccala on bread and shop in the Rialto Market. Then stretch your legs on the islands of the lagoon: Murano with its famous colourful glassware, the Lido for a beach and a short stop to photograph the Smartie-bright facades of the townhouses on Burano.

Where to stay:

Set in the walls of a former furnace, Lagare Hotel on Murano is now a tranquil spot with a cool, earthy palette in the rooms and an island that’s all yours once the day trippers leave. Be sure to book a visit to the nearby glass factory to watch the fascinating blowing process.


For many, Verona means opera. The massive amphitheatre has been showing opera since Roman times, when 30,000 spectators packed out the stands. The crowd size has halved but the operatic standard here is higher than ever. Book your tickets for summer months from the Arena website. Get a cheap seat on the stone benches.

In Verona town, drop in on the balcony that has served as a pilgrimage for Juliet fans for the last few decades. It has a very dubious claim for authenticity but it’s a must on the checklist. Move on swiftly to wander the markets in the piazza. Then on to Lake Garda for a speedy tour by powerboat, easily rented from the bank of the lake.

Where to stay:

Palazzo Victoria has its own romantic balconies. Behind the historic façade is a design-forward foyer and a series of calm, peaceful rooms. Due Torri Hotel Baglioni is a historic hotel with a beautiful vaulted lobby that doubles as a buzzing cultural hub for the city. There’s also an open-air rooftop bar, one of the highest in town. Stay out until the sunset matches the colour of your Aperol spritz.

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  • St Mark's square stands empty at sunrise, Venice. ©Matteo Colombo.

    Savour the emptiness…

    …Because, come February, the carnival takes over Venice. Though the city is madly busy, the masqueraded figures and spectacles are atmospheric, rather than riotous. Stay in the Lagare hotel.

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Naples – Sorrento – Amalfi – Capri

Best for… Dramatic film stars seeking a finale

The journey: 90 miles


Start out in Naples. The city’s reputation is on the grittier side. The grime and graffiti isn’t for everyone but, of course, it’s a great base for the coast, the Vesuvius bay area and a quick slice of pizza. Follow the tourist trail to Naples Archaeological Museum. The treasures of Pompeii and the rest of the classical world await – including a ‘secret’ room of erotic art and ancient scrolls.

All the tourists flock to the Antica Pizza trattorias for inexpensive offerings from tiny menus. Pizza Mondo has a wider selection: that is, if you’re looking for pizza, pizza and more pizza.

Drive an hour around the bay and end up in Sorrento. It feels like a resort here – much because many people start here on their adventures to Capri and the Amalfi coast. Neck shots of limoncello – the region’s famous drink, after every meal.

Where to stay:

You can’t miss the Grand Hotel Royal – it’s a sunburnt-pink building on the clifftop with an elegant interior and balustraded terraces. There are three bars and a swimming platform. Grand Hotel Excelsior Vittoria has seen it all before – including its fair share of royal visitors. This exquisite hotel has views of brooding Vesuvius and a spa in a renovated 19th century greenhouse. 


‘I want to be alone’ – Greta Garbo, who uttered these famous words as she fled the paparazzi, did not expect the world to follow her, but we did: to Ravello, Amalfi and colourful Postiano. These Amalfi coast towns are linked by a busy coast road above sheaves of cliff face. The roads are jammed in summer – out of season may be better for travelling by car. Otherwise, hike, or go by boat – just hold onto your hat.

If there was a colour to describe Amalfi it would be yellow – for its lemon groves, colourful facades and local Limoncello. Turn off the winding roads and book an excursion to swim in the Grotta dello Smeraldo for a splash of emerald.

Where to stay:

Miramalfi Hotel is outshone by its gorgeous terrace views of the lights of Amalfi away down the coast – but only just. There’s a pool and a restaurant with speciality coastal dishes.  


Visit beautiful Capri – home of the short trouser and the resealable orange juice… (not really, Capri is far too classy for either of these contraptions). After a jaunt on the coast, jump on a ferry and reach the chicest island of them all in three hours. It’s steep, very steep, and taking a car isn’t advised. Take your time in the heat and savour your well-earned solitude. Visit the Grotta Azzurra. The alien blue light that filters through the rock is unsurpassed.

Where to stay:

Capri Tiberio Palace is a small, friendly hotel, full of modern design, candy colours and inviting places to sit and read. It feels like a proper holiday home and comes complete with delicious Mediterranean dishes on the menu.

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