Four inspiring Italian itineraries

Eloise Barker

Title Photography by Noppasin Wongchum / Getty Images

Skip to Navigation

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 and following in the footsteps of gladiators at the Colosseum, 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 St Peter’s Basilica down an avenue of trees. Pre-dinner drinks are best served in the quieter Trastevere neighbourhood.

You’ll want to wake early to queue for the Vatican. Don’t forget to look out for Da Vincis and Caravaggios in the Vatican Galleries before seeking out the stunning Sistine Chapel.

Where to stay:

The Inn at the Spanish Steps is a small luxury hotel spread over multiple buildings. All the rooms are colourful and chic. For a complete mood shift, pop into the house nearby where the Romantic poet John Keats died of tuberculosis. If you want a super stylish room, The First Roma Arte 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.

Book flights to Rome

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. ©Ugur Keskin.

    Ice and sights

    You might admire your cone of ice cream more, but the Pantheon remains the largest unsupported dome in the world. On April 21 every year, light shines through the Oculus and creates an optical effect in front.

    Book flights to Rome
  • 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 flights to Pisa
  • 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 Etruscan tombs… and it’s also where they filmed certain sensationalist scenes from teen film franchise Twilight.

    Stay in Tuscany


Tuscany is a purple haze of hills where traditional village life prevails. Long driveways of poplars lead to old wine estates where time seems to slow down. Drive from hilltop town to hilltop town. 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 was famously the seat of the Medici family. Make sure to visit the Uffizi Gallery where you can admire some of the most renowned artworks in the world, including Botticelli’s Birth of Venus. Climb the Duomo and admire the bronze relief work on the baptistry, then 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 12th-Century castle with delicate frescos, wooden rafters and a sweeping gravel drive. Feel like landed Tuscan gentry eating the likes of pigeon at the Michelin-listed 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, home of the infamous Leaning Tower of Pisa. It’s smaller than you might expect but still exquisite, shining white under the sun. Climb the tower’s glistening marble steps for a strange, tilted experience. Don’t forget to ask someone to take a picture of you next to the tower, pretending to hold it up – this is practically mandatory for tourists.

Where to stay:

Set in a 19th-Century villa, Grotta Giusti Thermal Spa Resort is all about wellness. This hotel’s most spectacular feature has to be Grotta Giusti: the largest natural thermal grotto in Europe. Inside the mystical cave, you’ll find natural steam baths and a lake of warm thermal waters.

  • A statue in Pompeii. ©sestovic.

    Ancient wonder

    A day trip to Pompeii – a Roman town that was buried under volcanic ash when Mount Vesuvius erupted in AD79 – is both moving and educational. It’s a must-do for many when visiting Naples.

    Book flights to Naples
  • 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 in Milan.

    Book flights to Milan
  • Juliet’s balcony in Verona. ©druvo.

    Did you know…

    Though Shakespeare set three of his plays in 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.

    Book a holiday in Verona

Milan – Lake Como

Best for… The fashion set

The journey: 53 miles


If Rome is hot and lazy, then Milan is cool and industrious. Even outside of the famous fashion weeks, you’re sure to spot Salvatore Ferragamo-shod socialites pounding the streets. For a different kind of style, Milan’s cathedral is essential viewing. This Gothic marvel took almost six centuries to complete. It’s both beautiful and overbearingly detailed.

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

Sforza Castle is a Milan landmark housing multiple museums and Michelangelo’s last (and unfinished) sculpture. If you’re a lover of art, you’ll also want to see Leonardo da Vinci's The Last Supper at the Santa Maria delle Grazie convent. Book ahead to ensure entry.

Where to stay:

Hyatt Centric Milan Centrale boasts an excellent location, with Milan’s main train station just a short walk away. If you’re after something a little different, book one of the enchanting rooms at Chateau Monfort. Inspired by fairy tales and operas, this hotel is chock-full of charm.

Lake Como

Pick up your car and drive to Lake Como. This beautiful lake at the foot of the Alps snakes along a shore lined with posh villas and holiday homes. Glamour reigns supreme here, so pack a pair of oversized sunglasses and, if you’re in a convertible, drive with top down. You’ll feel like a film star in no time.

Stop off in gorgeous little towns like Bellagio, known as the ‘Pearl of Lake Como’, where you can seek out plenty of glitz and spritz cocktails. In the evening, drop into a bar for an aperitivo before filling up on fabulous seafood.

Where to stay:

Grand Hotel Tremezzo is elegant and opulent, filled with delights such as a floating pool in Lake Como. Stunning vistas of the glittering lake and surrounding Alps are easy to come by – whether you’re lounging by a pool or dining by candlelight on a terrace – and sophistication is seeped into every detail. Be sure to pop into the nearby Villa Carlotta’s botanical gardens, full of mature azaleas and tip-top trimmed topiary.

Book flights to Milan

Venice – Verona

Best for… Romance on a grand scale

The journey: 75 miles


Ah, Venice. In this beautiful, sinking city you can’t walk far without finding water. Cross arched bridges over gondola-lined canals, get lost in labyrinthine alleys and stumble upon small cobblestoned squares. Then seek out St Mark’s Square – large and bustling with tourists – on the edge of the lagoon. Admire St Mark’s Basilica and the Doge’s Palace before climbing to the top of the Clock Tower.

You can see most of the city’s highlights in a couple of days. In addition to St Mark’s Square, top spots include the chic Peggy Guggenheim museum and Rialto Bridge. When you need a break from all the sight-seeing, stop in a cafe or bar to fuel up with an espresso or Aperol spritz. Pick at cicchetti and watch the world go by. Don’t forget to grab a souvenir – you can browse for a Venetian mask in an authentic workshop like Ca’ Macana even if you’re visiting outside of carnival season.

If you’ve got some extra time, explore beyond the main island via vaporetto (water bus). Head to Murano for its colourful glassware, Lido for its beach and Burano for its Smartie-bright townhouses.

Where to stay:

Discover Venice’s lagoon from Hyatt Centric Murano Venice. This chic hotel is set in a former glass factory, featuring terracotta walls and large, arched windows. There’s a vaporetto stop close by so you can easily set off to see other islands.


For many, Verona means opera. The massive amphitheatre has been around 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 speedboat tour: charters are available from several locations

Where to stay:

Due Torri Hotel is a luxury hotel set in a 14th-Century palace in the historic centre of Verona. Most rooms are decorated with tapestries and period furniture, making them rather regal. There’s also an open-air rooftop bar, one of the highest in town, where you can stay out until the sunset matches the colour of your Aperol spritz.

Book flights to Venice

  • 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.

    Book hotel

Naples – Sorrento – Amalfi – Capri

Best for… Dramatic film stars seeking a finale

The journey: 111 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.

Make your way down UNESCO-protected street Spaccanapoli – the ‘Naples splitter’ – which cuts through the city centre. Stop to admire art-filled churches along the way. If you only enter one church, make it the Cappella Sansevero where you can admire the exquisite marble sculpture ‘Veiled Christ’ by Giuseppe Sanmartino. Then wander down Via San Gregorio Armeno for an unusual souvenir. This packed street is known for its shops selling eclectic nativity figures. We’re talking pop stars and politicians – pick up a Lady Gaga figure if you feel like she’d make a great addition to your scene.

Drive around 30 miles to Sorrento. It feels like a resort – much because many people start their adventures to Capri and the Amalfi coast from here. Neck shots of limoncello – the region’s famous drink, after every meal.

Where to stay:

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.


If there was a colour to describe Amalfi it would be yellow – for its lemon groves, colourful facades and local limoncello. Hop between coastal towns for sigh-worthy views of cliffs covered in greenery and sandy shores lapped by shimmering water. Flock to charming Ravello, colourful Positano and, of course, Amalfi. During your journey along the coast, make a stop at the Grotta dello Smeraldo for a splash of emerald.

Amalfi’s 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, go by boat.

Where to stay:

Anantara Convento di Amalfi Grand Hotel promises a peaceful stay with stunning views. The building, built into a cliffside, dates back to the 13th Century and used to be a convent. Lounge by the infinity pool on the edge of the cliff or walk into Amalfi town centre, which is less than half a mile away.


After a jaunt on the coast, jump on a ferry and reach the chicest island of them all: Capri. It’s steep, very steep, and taking a car isn’t advised. Take the funicular up to Capri town and browse high-end boutiques, stopping off for a zesty lemon granita when you (and your wallet) need a break. Go further up the hilly island and take a charming chairlift ride to Anacapri, where you’ll be rewarded with a magnificent view of the coast and cliffs. Before you leave Capri, visit the Grotta Azzurra. The grotto is known for its illuminated, otherworldly water. Board a boat to reach the grotto but expect to queue – it’s very popular.

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.

Book flights to Naples