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A lifetime may not be enough to see all the wonders of Italy, but that doesn't mean you shouldn't try. Each Italian city is a treasure trove of art, architecture, and historical monuments, while the countryside is filled with breathtaking vistas, unique cuisines, and famous wines. If you're at a loss for where to start, it's worth developing a list of regions or cities you want to cover rather than winging it. You can choose to explore Tuscany, the Amalfi coast, or Sardinia, or pick the 'Holy Trinity' of cities — Venice, Florence, and Rome, as your introduction to the Italian essentials. Whether you pick the fashionistas of Milan, Pompeii's ruins, frescoes at the Vatican, or opera in Verona, Italy will never disappoint.
Italian phrases will come in handy, especially when you are lost in small-town Italy's winding roads, or trying to order the daily special at a trattoria. Food and drink are passions in Italy, so be sure to indulge in all the different regional cuisines and wines, and linger over a cup of coffee at the local piazza. Traffic rules are more of a suggestion than rule to motorists, so look both ways twice before stepping into the street. Trains are the easiest and cheapest way to travel between cities so it may be worth investing in a Trenitalia rail pass for the duration of your stay.
There are several Italian international airports to fly to including Rome (FCO or CIA), Milan (MXP, LIN, or BGY), Pisa (PSA), Venice (VCE), Bologna (BLQ), Naples (NAP), and Palermo (PMO). Which airport to fly to depends largely on where you'd like to begin your Italian journey, and if you're on a low-cost or full-service international airline. With the exception of the summer holidays between June and early September, and the Christmas and Easter breaks, cheap flights to Italy are easy to find simply because of the sheer number of airlines that fly this route. These include Air Canada from Toronto, Air Transat from Montreal, British Airways, KLM, Lufthansa, and Air France.
Depending on where you are in Italy, the weather can be quite varied so a little research on the area you're visiting would be wise before you leave. In general, July to September is warm, with heavy rains likely in September. Winter snowfall varies from region to region, but generally begins in November and lasts well into February in some areas. Temperatures are much milder toward southern Italy and the islands of Sardinia and Sicily. Inexpensive flights and accommodation rates are generally available between November and March (except for Christmas) so you could still enjoy good weather in the south without spending a fortune on flights and hotels.