By Rocky Casale
February 20, 2018
Aerial view of Bergamo old town cityscape, Lombardy, Italy
Credit: Alexander Spatari/Getty Images

Deciding where to travel in Italy — and when — all boils down to taste. Beaches or vineyards? Bustling cities, or quiet and secluded rural destinations? Weather can impact your decision making, as will your travel budgets. But travelers should also take into consideration national holidays and other factors that can influence crowds and prices.

Here, we break down the best and worst times to visit Italy for every type of vacation.

The Best Months to Visit Italy

The Best Times to Visit Italy's Beaches

Spring, summer, and autumn are heralded as the best times to visit Italy. The problem with late spring and summer, however, is that everyone has the same idea: including Italians with second homes by the sea. Umbrella and beach chair rental prices are exorbitant, and the beaches are crowded and noisy. Look instead to smaller villages near the sea, like Terlizzi in Puglia, where the sea remains warm through late October, and nearby beaches are quiet.

The Best Times to Visit Italy for Wine

In Terlizzi, for example, American expats Paul Cappelli and Steven Crutchfield own Villa Cappelli in Terlizzi. During the late and off season, rates are reduced from €100 to €80 (or just shy of $100) per night — and guests can enjoy some of Italy's finer offerings (think: wine and food). At Villa Cappelli, guests experience wine tastings with regional sommeliers, cooking classes, and cultural tours of Puglia. Their olive harvesting experiences are phenomenal, and give guests the opportunity to sample some of the finest olive oils in the world.

And in November, the recently remodeled Venissa — a small boutique resort on the islands of Mazzorbo and Burano — celebrates the harvest of their Dorona vineyard. It's one of the most exclusive and prized vineyards in Italy. Owner Matteo Bisol hosts wine dinners and tours of Torcello Island’s Cathedral of Santa Maria Assunta, the oldest church in Venice filled with spectacular Byzantine mosaics.

Mazzorbo and Burano, both a quick 30 minute boat ride from the main city of Venice, are also home to outstanding lacemakers, and a beautiful fish market where local fishermen haul in their catch, roll up their sleeves, and fry seafood for guests on the spot.

The Cheapest Times to Visit Italy

Rome and Venice are bucket list cities, and visitors to Italy usually begin their trip in Rome, either flying into or connecting through Fiumicino Airport.

Meridiana Airlines offers unheard of round trip flight deals between May and October, when they fly New York City to Rome (or to, Naples or Milan) for well under $500.

Rome, like Florence, is inundated with tourists almost anytime of year except winter. This is a lovely time to visit, despite the occasional rain storm, as the city’s attractions are not busy. Hotels, like the new Le Méridien Visconti, located closer to the Vatican, are particularly affordable this time of year.

One hour south of Rome by train is Naples, and local Tren Italia and Italo trains typically offer cheaper tickets when they are booked online in advance. Naples in the off season is nothing short of magical, and a popular destination for Italians who travel here to tour the city’s Christmas markets, which are some of the largest in Europe.

The Worst Times to Visit Italy

The Worst Times to Visit Italy for Crowds

Avoid at all costs Venice during Carnival if you abhor crowds. Hotels are at a premium, and the city’s bridges, boats, and attractions lose their charm, blocked as they are by hoards of mask-wearing revelers. For a real taste of Venice, the northern lagoon in either March or November is sublime.

Tuscany is also on most people's radar, especially in the summer and autumn. This is bad news for travelers wanting to see Florence, Siena, or medieval hilltop towns like San Gemigano, which become clogged all day long with travelers.

Tour busses logjam roads, museum lines are terrifying, and it’s hot as a crucible. Consider seeing these places during the off season and from afar, by renting a room at Monteverdi, in Tuscany’s Val D’Orcia region. From November through April rates are slashed, and the resort is an easy day trip from destinations like Pienza and Florence. Monteverdi’s spa and restaurant are open all year, and guests can experience Tuscany truffle hunting, wine tasting, or cooking classes in the village of Castiglioncello del Trinoro without having to journey far — thus saving on travel expenses.