Here’s a month-by-month guide to get you started…
Florence is, of course, the cradle of the Renaissance, and it’s the city’s remarkable architecture and art that are the main draw for tourists. This means long queues for several of the key museums and churches at most times of the year. But in January you can enjoy the art and the sights – most of which are indoors – entirely free of crowds. There’s great shopping to be had, too – especially during the January sales – and it’s an excellent time to make the most of the best bars and restaurants.
See our guide to the best hotels in Florence
Always beautiful, always alluring, always romantic and never disappointing: you can’t go wrong with Venice at almost any time of year. But, while it can undoubtedly be chilly, there is a special magic to the city in winter. On clear days, the canals sparkle in the sunlight, and you can see the snow-capped Dolomites on the horizon. In February you can also choose between crowd-free sights coupled with bargain prices, or the excitement and glamour of the Carnival (February 8 – 25, 2020).
See our guide to the best hotels in Venice
It’s the amazing variety which makes Sicily so special – from smouldering Etna, to stunning baroque towns and fabulous Greek and Roman ruins. But the sights are spread all over the island so you need to spend time on the road to link them all together. So March, when the weather is just beginning to warm up, yet the roads are quiet, is a great time to consider a trip. Plan to circumnavigate the island – you’ll need two weeks, but the highlights can be squeezed into a week.
See our guide to the best hotels in Sicily
This fascinating town of caves, rock churches and grottos has been transformed by new hotels, its Unesco World Heritage status – and its stint as 2019’s European Capitals of Culture (the other was Plovdiv, Bulgaria). It’s a great option for an offbeat city break, especially near the start of the year – spring comes early this far south. There’s some interesting local cuisine, too, and fine wines from the wider Basilicata region, based on some rare and historic grape varieties.
See our guide to the best hotels in Matera
Venice and Verona are the famous draws in the Veneto, but there is so much more to enjoy. Padua and Vicenza each make weekend breaks in their own right, as does Vicenza, home to several buildings by Palladio and arguably one of the most beautiful small towns in Italy. Palladio was also responsible for some of the grand villas built by the richest Venetian families along the Brenta canal between Venice and Padua – an excellent short cruise. Further north you find the Prosecco vineyards, and in the mountains, the winter (or summer) resort of Cortina d’Ampezzo.
See our guide to the best hotels in The Veneto
If March is a good time to think about touring Sicily, April, when the sun is getting higher and the days are pleasantly warm, is perfect for a weekend break to this wonderful Sicilian hilltop resort. Famous for its panoramic views of the sea and Mount Etna from the ruined Roman theatre, it is also home to some of Sicily’s best hotels and restaurants. DH Lawrence came here in the Twenties and loved it – it is just as seductive a century later.
See our guide to the best hotels in Taormina
Ever since the (admittedly somewhat debauched) Emperor Tiberius went to Capri to avoid the pressures of running an empire, this lovely island just off the Sorrento peninsula has been about escapism. To make the most of it today you have to do a bit of extra escaping by avoiding the crowds of day trippers who arrive by boat from mid-morning to mid-afternoon. But you can make this a positive by heading off on the footpaths or beaches when they arrive, then returning to enjoy the more peaceful the evenings.
See our guide to the best hotels in Capri
Puglia is most famous for its idiosyncratic, conical-roofed trulli houses, and its fabulous masseria hotels which have been converted from traditional fortified manor houses. But the long coastline makes it a good choice for a seaside holiday, and the appeal of the historic medieval ports of Bari and Brindisi, as well as the city of Lecce are often overlooked. Because its so far south, Puglia is also great for an early or late season break. By May it will already be properly warm and the strawberries and peaches will be ripening.
See our guide to the best hotels in Puglia
Tuscany’s great rival is just as beautiful as its neighbour, especially in the wooded foothills of the Apennines in the east of the region and the rolling landscape of the south. There are also delightful historic hill towns – Perugia, Assisi which attract their fair share of pilgrims and crowds, but also smaller Spoleto, Spello and Orvieto, just as fascinating but not nearly so well known. In June prices for villas and hotels are well below peak rates, and the countryside, flecked with myriads of poppies and sunflowers, is at its most colourful.
See our guide to the best hotels in Umbria
Most of Piedmont comprises the foothills of the Alps which tumble down towards the Italian Riviera. It’s a beautiful landscape and especially lovely in the early summer Come for Italy’s richest culinary tradition and its finest red wine – Barolo. Piedmont takes its food very seriously; it’s home to the Slow Food movement, excellent beef and the delicious white truffle, though you’ll have to come in November to taste that – a city break in the capital, Turin, perhaps.
See our guide to the best hotels in Piedmont
More compact than Florence, and arguably more beautiful, Siena is one of the most unspoilt towns in Europe – architecturally much still dates from its medieval heyday. And the reason to come in July is because of another survival from that era – the extraordinary and hugely exciting Palio horse race which takes over the main square twice a year (July 2 and also August 16). You don’t have to pay a fortune to watch from a balcony window. Just come to the square a couple of hours before the race, bring plenty of water and enjoy the spectacle.
See our guide to the best hotels in Siena
Forget Romeo, it’s Rome that makes Verona special. You’ll find it everywhere in this ancient, compact and sophisticated city – poking out of the corner of a street, or incorporated into a Renaissance church. But the most spectacular relic of its Roman past is, of course, the amphitheatre or Arena which hosts the open-air opera festival every summer. It’s one of Europe’s great cultural institutions and a key reason to plan your visit in July.
See our guide to the best hotels in Verona
The point where Italy meets Austria and Switzerland is one of the most beautiful parts of the Dolomites and a great destination for a summer escapist holiday, whether you want to hike, bike, or just spend some time enjoying the view. And if you want to avoid too many uphill slogs, you can always use a chairlift from one of the winter resorts. The cultural confusion – many locals speak German rather than Italian – adds to the appeal, especially in the cuisine: restaurant menus might list goulash, risotto, schnitzel and pizza.
See our guide to the best hotels in South Tyrol
Naples, Pompeii, Herculaneum and the Sorrento peninsula, as well as the islands of Capri, Ischia and Proceta are the region’s most popular destinations, but they represent only the northern chunk of Campania. Head further south, beyond Salerno, the coastline flattens out into the Cilento National Park – one of the biggest in Italy, and another World Heritage Site. There are miles of sandy beaches to enjoy, as well as the Roman ruins at Paestum. Head further south still and you get to more mountainous, spectacular and remote country, little visited by tourists.
See our guide to the best hotels in Campania
The Italian Lakes
Holidaymakers have been attracted to the lakes since Roman times, and each has its own special character and appeal. If you’re after a quieter romantic escape, you may be drawn to Lake Orta or Lake Como. Outdoorsy types should head to the northern shores of Lake Garda for canyoning and kite surfing, while Lake Iseo is well-suited to hikers and cyclists. And for opulent hotels, and grand resorts, Stresa, Pallanza, and the Golfo Borromeo of Lake Maggiore are the places to stay. The September weather is usually idyllic.
See our guide to the best hotels in the Italian Lakes
There is nothing complicated about what the Amalfi Coast has to offer. Quite simply it is one long sunny, south-facing balcony overlooking the warm Tyrrhenian Sea, and is ideal for an ultra-relaxing seaside holiday, especially in spring or autumn. The roads are slow and winding, but there are plenty of boat trips along the coast. Choose between the chic hotels stacked up on the cliffs above the beach at Positano or Ravello; the livelier atmosphere of Amalfi, or one of the smaller villages such as Praiano.
See our guide to the best hotels on the Amalfi Coast
Tuscany encapsulates everything that is most seductive about Italy – glorious landscapes, perfect climate, great art and architecture and a matchless cuisine. For the best of that cuisine, go in the autumn, when the light turns golden, the days are still warm, the rich harvest of figs, grapes, chestnuts, olives, apples, pears and pumpkins is at its peak, and fresh funghi are being gathered in the woods. A succession of local village festivals pays homage to the harvest – you’ll never enjoy a better feast.
See our guide to the best hotels in Tuscany
Amalfi is on the south, Sorrento on the north side of the peninsula that edges the great Bay of Naples. Don’t go to this historic resort for a beach holiday, however. While there is a small town beach, most of the rest is clustered along the top of the cliffs above. This is a place to enjoy the autumn sunshine, strolling between outdoor cafés or relaxing in hotel gardens. It’s also ideal for day trips to Naples or Capri (by ferry) or Pompeii and Herculaneum (by rail).
See our guide to the best hotels in Sorrento
In many minds Milan is defined by its famous fashion brands, and, perhaps, La Scala opera house. But it is also a great destination for a cultural trip. As well as the opera, there are several excellent art museums, including the Brera, which holds one of the best collections of Renaissance art in Italy, and the legacy of Leonardo da Vinci – notably his Last Supper and his notebooks, some of which are on display in the Ambrosiana Library. Milanese cuisine – based as much on risottos as on pasta – is a highlight.
See our guide to the best hotels in Milan
The world’s greatest historic city with fabulous sights ranging from the Colosseum to Michelangelo’s Sistine Chapel ceiling, from remarkable Baroque churches to the catacombs, Rome has its appeal at almost any time of year. But winter is an especially good choice. The sights are much quieter, but it’s also a surprisingly cosy: some restaurants even have a roaring open fire in the dining room. And, the build-up to Christmas is especially atmospheric.
See our guide to the best hotels in Rome