How far in advance should you plan an Italy trip?

When should you start booking your trip? Italy is one of the most visited destinations in the world, so in our opinion, it is never too early to start the booking process. Book accommodation as soon as possible, and at least 6-12 months in advance especially for peak times in July and August.



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“Aside from winter travel, shoulder season (March through May and September through November) is known for cheap Italy deals,” he shared. If you can hold out until the end of the spring shoulder season, you'll be rewarded with pleasant temperatures in the mid to high 70s across the country, according to WeatherSpark.

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April to June offers the best weather Often considered the best time to visit, spring offers the ideal mix of good climate and bearable tourism flows. Nature blooms as the snow melts in the mountains and the rolling hills of the central Italian countryside come to life after the chilly winter.

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April to June offers the best weather Often considered the best time to visit, spring offers the ideal mix of good climate and bearable tourism flows. Nature blooms as the snow melts in the mountains and the rolling hills of the central Italian countryside come to life after the chilly winter.

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Peak season, particularly the months of July and August (and even extending into September and early October), is generally considered a very busy and expensive time to visit Italy's cities and major tourist areas like the Amalfi Coast and Cinque Terre.

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While you can make local friends on trains or experience rural life on a road trip, there's no better way to see Italy than with the help of a local tour guide.

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Unless your flights are both in the middle of the night, stay only one night in Pisa and spend the rest of the time in Florence. Pisa is a nice little town. Florence is one of the most wonderful cities on the planet.

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Rome, Florence, and Venice are the three most popular cities to visit on a first trip to Italy. These are filled with some of Italy's most famous places and it is easy to get around using public transportation. The Amalfi Coast, Cinque Terre, and/or Milan can easily be added on to this trip.

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If you ask locals “Do you tip in Italy?”, they'll explain that while they sometimes leave a small tip, it's generally not necessary. In Italy, gratuity (or una mancia, pronounced oo-nah MAN-chah) is considered a bonus for exceptional service. And it's not often that you'll find a tip jar at a register.

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However, to experience Italy at its best, you'll need to factor in three or four weeks. That way, you'll have enough time to discover a large part of the peninsula and one (or perhaps both!) of its major islands, Sardinia and Sicily.

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How to plan an Italy trip
  1. Step 1 – Decide when you want to go and your budget.
  2. Step 2 – Do some preliminary research and preparation.
  3. Step 3 – Confirm your itinerary.
  4. Step 4 – Book your flights, inbound travel & insurance.
  5. Step 5 – Book accommodation and transport.
  6. Step 6 – Book Attractions, tours and activities.


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The rainiest months almost everywhere in Italy are usually October and November. While some areas in central Italy like Milan and Venice witness rainfall pretty much throughout the year, cities in southern Italy like Rome and Naples experience rainfall mostly during the winter season.

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Spring and autumn are the ideal seasons for sightseeing in Italy: not only are all attractions open but you won't need to stand in long queues to enter (like in summer) and you'll have fewer crowds to contend with. Winter is also a good time if you're thinking about hitting museums and galleries.

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The two shoulder seasons on the Amalfi Coast are September to October and April to May. They also happen to be two of the best times to visit, since the days tend to be sunny and warm. With fewer crowds and minimal rain, both are ideal times to enjoy the scenery.

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If you're in Naples or on the Amalfi Coast, Pompeii is a must-visit attraction that no one should miss. This massive archeological site is the best way to glimpse the daily life of ancient Romans. We highly recommend taking a Pompeii tour to fully appreciate the history here.

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The southern shore of Lake Como is just 32 miles (51 km) from Milan. This iconic Italian lake draws visitors from around the world, and with good reason.

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