The 10 ultimate Italian holidays, and how to do them in style


It is the travel news many of us have been waiting for. Especially those of us who dream of a nice glass of chianti on a warm evening, a sunny stroll through a broad piazza, a day of high art in glorious galleries, a villa in the Tuscan hills or a week on an Adriatic beach.

As of this morning (March 1), Italy is back on the map as a realistic destination for getaways in the spring and summer that are just over the horizon. Prior to today, the land of Pompeii, prosecco and puttanesca was a tricky holiday proposition, demanding that even fully vaccinated visitors pass a PCR test to enter the country. But with a new month comes new openness. Italy is now accessible to tourists via proof of full vaccination – or, if you cannot provide this, through a negative test result or certified recovery from Covid.

Of course, there are caveats to this happy headline. For one, there is the small obstacle that you still need a “Green Pass” (which is only available if you are fully vaccinated) to enter bars, restaurants and other venues. But even here, change is afoot. “We will gradually put an end to the enhanced green certificate obligation, starting with outdoor activities including fairs, sports, parties and shows,” the prime minister Mario Draghi announced last week. Although he was unspecific on dates, the message was clear. The Italy that we all know and love from visits before the pandemic will be back online soon.

Good enough reason to plan a break immediately? Absolutely. And if you are hankering for anything from a Milanese shopping trip or a romantic weekend in Venice to a Sicilian villa and a fortnight away with the grandchildren, the following options will have appeal.


Ideal for: Couples craving a long weekend in a special setting

When to go: March or April

There is no time like the present for seeing La Serenissima at its best. Famously busy in summer, Venice presents a calmer face in spring. Go this month, and you should have St Mark’s Square and the Rialto Bridge, if not to yourself, then with more room to breathe than in August. Wander out at night, meanwhile, and you should find that, with the day-trippers gone, March’s cooler temperatures equate to quieter restaurants and a gentle vibe.

venice italy holidays best places go travel

Venice has a reputation for romance

Credit: Getty

How to do it

A four-night stay at the five-star Bauer hotel, flying from Heathrow on March 23, starts at £518 per person via British Airways Holidays (0344 493 0787;


Ideal for: Stylish shopaholics and fashionistas

When to go: May

Italy’s fashion capital fully lives up to its chic image. The Galleria Vittorio Emanuele II is one of the planet’s most gorgeous shopping zones – not least because its boutique-lined arcades give onto the Piazza del Duomo, where the city’s magnificent 14th century cathedral holds court. There are further fashionable stores on the elegant Via della Spiga, while a true art wonder – Da Vinci’s The Last Supper – waits at Santa Maria delle Grazie.

Best Italy holidays

There are few more stylish city breaks than Milan

Credit: Nikada/iStock Unreleased

How to do it

A four-night stay at the four-star Hotel Manzoni, flying from Luton on May 11, costs from £570 per person, via easyJet Holidays (0330 551 5151;


Ideal for: History buffs who want to head straight to the source

When to go: September

Few cities revel in their back-story quite like the Italian capital. Indeed, it is impossible to avoid this grandest of yarns – in the epic curve of the Colosseum, or the tumbled temples of the Forum. But there is also a Rome that exists between ancient and modern, and early autumn is a fine time to see it – when tourist numbers and temperatures have fallen.

Best Italy holidays

Step back in time with a visit to Rome

Credit: Fernando Manoso/FEMA

How to do it 

Martin Randall Travel (020 8742 3355; has an “Early Christian & Medieval Rome” group tour slated for September 20-27. This eight-day affair will peer at the millennium that followed the Roman Empire, via churches like San Clemente and Santa Cecilia, and the nearby hillside town of Viterbo. From £3,310 a head (with flights).


Ideal for: Art lovers keen to feast on wonder after wonder

When to go: May

If Rome is the epicentre of European history, Florence is the artistic core; the “Birthplace of the Renaissance” where you can barely move an inch without spotting a treasure that pushed civilisation forward. Botticelli’s The Birth of Venus in the Uffizi, Michaelangelo’s David in the Accademia, Raphael’s La Donna Gravida in the Pitti Palace. Take your pick.

Best Italy holidays

Beautiful Florence is paradise for art lovers

Credit: Julian Elliott Photography/Stone RF

How to do it

Kirker Holidays (020 7593 1899; offers a best of both worlds in “Florence & The Tuscan Coast”, a six-night escape that splits its time between the city and the Tyrrhenian Sea at Punta Ala. From £1,989 per person (with flights and rental car).


Ideal for: Families wanting easy relaxation on the shoreline

When to go: August

Italy’s second largest island has a reputation as a rocky crag rising from Mediterranean depths. It is a fair image too – not least where the Gennargentu massif rears up at its heart. But for every hard mile of ridge line, there is a soft equivalent by the water – especially along a south coast that is perfect for at-ease family trips once the school year has ended.

Best Italy holidays

Sardinia’s coastline blends both rocky ridges and exquisite sandy beaches


How to do it

A seven-night half-board holiday for a family of four at the Hotel Stella Maris (a four-star with a private beach, just outside south-easterly Villasimius), flying from Gatwick on August 6, costs from £7,332 in total via Citalia (01293 324 634;


Ideal for: Multi-generational family groups looking to catch up

When to go: July

If Italy’s second largest island is perfect for beach breaks with children, its biggest is a place for getaways with the whole family – in a villa with a pool for splashing about, a shady veranda for when the sun is up, and enough rooms that everyone has space. Sicily, not just Italy’s biggest island, but the Mediterranean’s too, has suitable properties aplenty.

Best Italy holidays

On Sicily too, beach lovers are spoilt for choice

Credit: domeniconardozza/iStockphoto

How to do it

Sicily4U (01483 497 060; offers Villa Aronica, a seven-bedroom retreat with a pool at San Vito Lo Capo in the far north-west of the island. It can be hired for the week starting July 9 for €6,760 (£5,626) in total; from €3,340 (£2,780) at other times (flights extra).


Ideal for: Unhurried travellers who want peace and quiet

When to go: June

If you are of a nobly fine vintage where you want little of your holiday except a place in the sun and the sort of silence that will let you get through three or four novels in a week, Italy’s southeasternmost region will oblige. Puglia is all small towns and olive groves – largely rustic, and not too fussed about changing its tune. Tranquility comes as standard.

Best Italy holidays

Bosco Degli Ulivi, a splendid retreat with a garden in Puglia

How to do it

The Thinking Traveller (020 7377 8518; offers Bosco Degli Ulivi – a splendid three-bedroom retreat with a garden, just above the Puglian south tip at Torre Vado. It is still available for the week of June 18, from £5,087 (flights extra).

The Amalfi Coast

Ideal for: Couples of all ages seeking a spot of together-time

When to go: June

Is there a more romantic destination anywhere in Europe than the 34 miles of the Italian seafront where Positano and Ravello preen in the sun below towering cliffs, and island oasis Capri shimmers in the sun-sparkle directly to the west? Ponder this question at your leisure, with a cocktail in hand, on a hotel terrace in Amalfi itself. No rush on the answer. 

Best Italy holidays

There’s very little in Italy can rival the beauty of the Amalfi Coast

Credit: Francesco Riccardo Iacomino/500px Prime

How to do it

Scott Dunn (020 3553 1641; maximises the romance factor with a nine-day “Honeymoon on the Amalfi Coast” that cools its heels in boutique retreats in Praiano and Ravello, and on Capri. From £5,400 per person, including flights to Naples.

The Neapolitan Riviera 

Ideal for: Adventurous families chasing Italy beyond the beach

When to go: April

The wider Neapolitan Riviera isn’t just the sumptuous scenery and sunset evenings of the Amalfi shoreline. It can also be a playground for families – where Naples is the spiritual home of all things pizza, a notoriously tetchy volcano looms large, and a world-famous ruin brings ancient history to life; enough to enthral even the most easily bored youngster.

Best Italy holidays

Bring history to life for children with a visit to Pompeii

Credit: Didier Marti/Moment RF

How to do it

Exodus Travels (020 3553 1643; offers a “Pompeii & Pizza Family Holiday”, an eight-day group jaunt that ticks off the best of the Neapolitan region. Two editions are due in the Easter break, from £1,699 per adult, £1,275 per child, with flights.


Ideal for: Anyone who has ever considered an Italian holiday

When to go: August

If all else fails, there is always the undying allure of a week in the Italian region most beloved of British tourists. Hilltop citadels, whispering vineyards, trattorias serving local delights, the possibility of a drive to the city for art and lunch. Tuscany rarely disappoints.

How to do it

James Villas (01622 655 900; has a wealth of properties in the region. Including Villa Al Povero (ref: 9656), a farmhouse set midway between Florence and the coast, near the Etruscan town of Volterra, that sleeps up to 10 in six bedrooms. It can be rented in August for £5,099 per week; from £3,599 in other months (flights extra).

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