Don’t come in August
I’ve said this many times, you can visit throughout the year so don’t come in the most overcrowded, hot and humid part of the year when most Italians are on summer holidays you will be uncomfortable and will never have an authentic experience.
September will be just as beautiful, autumn/fall will give you an excuse to taste the new wine, eat truffles and mushrooms and visit museums. Christmas and New Year are filled with traditions and delicacies. Easter and Spring are perfect for the mild weather and religious festivities.
Simply do your research, and discover whatever your heart desires to experience on the peninsula, visiting archaeological sites in May will be so much better than in the heat of August, museums are less crowded in the winter, and food, music and religious festivals happen through the whole year and the best time to experience Italian culture in the theatres is actually in the middle of winter (Feb/March).
But then if you have your vacation in August and can’t get here any other time, then come Italy in August isn’t impossible it’s just hot and in holiday mode. Simply try to stay cool by heading to the mountains or the beach and try to stay put during the week of Ferragosto (15th August) which is when the country has its main summer holiday, where you will find most places closed.
Avoid the trains in the South, unless …
Italy is perfect for slow travel, Italians are never in a hurry so you can take the time to savour a good meal, take a bus tour or the train. From Rome upwards, train journeys are fast, easy and affordable. But in the south things are not so easy, so unless you want to descend slowly into Dante’s Inferno with endless delays and cancelled trains simply avoid long train journeys. It’s easy to get a cheap flight down from Rome to Catania or Palermo and avoid the hassle.
Unless of course, you have time for a long-winded adventure. Once you are in Sicily for example feel free to take a shorter journey, day trips on the trains are fun, and great for families, just be sure to take a packed lunch and give yourself plenty of time to arrive at your destination. Go around the Mt Etna volcano on the Circumetenea historical railway, plan a trip from Palermo to Messina along the panoramic coastline or check out the new 50 Treni Storici (historical trains) which have been designed to offer their passengers stops at Sicilian wineries and other towns fine food is produced.
Get out of the major cities
There is nothing wrong with first-time visitors visiting the major Italian capitals, but try to make it into smaller towns. Italy is such a rich place to explore, hire a car and go track down a food festival or a well-known church, museum or villa you once read about in a magazine.
Yes, Tuscany is Florence but it is also Lucca, Siena, Vinci, San Gimignano and other 276 Tuscan towns to explore, each with its own food, traditions, history and festivals.
Why not pick another region to visit try Emilia Romagna in the north with cities like Piacenza, Parma, Reggio Emilia, Modena, Bologna, Ferrara, Forlì and Rimini.
In the region of Piemonte there is Turin, Cuneo, Asti, Alessandria, Vercelli, Novara, Biella or Verbano.
In the south dive into Puglia with towns like Bari, Foggia,Lecce, Taranto, Brindisi and Barletta. Calabria is filled with possibilities and much fewer tourists than the seaside town of Tropea or Isca Marina or Reggio which is connected to Messina and is a perfect gateway into Sicily.
Be brave, hire a car
People are a little hesitant to drive in Italy, but if you get a chance to hire a car it is worth the challenge and expense. Driving around Italy will give you a chance to be autonomous, travel and stop where you like and it allows you to get a sense of the landscape and geography of the place. Yes, you will see some reckless drivers speeding past you, and be frustrated by a lack of parking and autostrada fees but if you go off the beaten track you can avoid many of these problems.
Learn a little Italian or at least get a guidebook
There is no need to be a fluent Italian speaker, but your visit will be so much better if you put in the effort to understand Italian culture, history and language. There are many great guide books which will give you a good general introduction and help you to do basic things like ask for directions or say please and thank you.
See something authentic
Please stay away from tourist traps, in Italy, there is so much more than pizza and pasta. Go to eat at a Trattoria (family-run restaurant) where you will be treated to a good home-cooked meal. Go to a Sagra (local food festival), which happens all the time and gives you a chance to taste local delicacies for a handful of Euros.
Experience local markets, there are always open-air markets, some are dedicated to food, others to flowers and many sell arts and crafts or antiques even if you don’t buy anything it is a unique experience to immerse yourself in.
See a patron Saint celebration, every town has a Saintly protector celebrated during the year with their own local holiday, filled with markets, religious processions, fireworks, Sagras, brass bands, free concerts, art exhibitions and also usually specially prepared dishes or sweets dedicated to each particular saint.
Every town will have its own local speciality, a particular type of pasta, wine, dessert, seafood dish, cheese, bread or local seasonal product. Taste it all!
Don’t be in a hurry
Don’t be in a rush as Italians are never in a hurry, they are always fashionably late, and they take their time to talk, taste and savour life. When you are visiting their country try to leave space for the unexpected.
Slow food and travel make their home in Italy which gathers experiences rather than ticking off names on a bucket list.
Dive into the history and culture there’s plenty of it
Not even Italians are fully aware of all the history surrounding them, but if you want to appreciate this country, you should know a little.
In Sicily alone, there have been thirteen different invaders who have ruled over the island which has been inhabited since prehistory. Each invading culture has left behind distinct monuments and cultural footprints all over the island. From the Phoenicians, Greeks, Romans, Vandals/Goths, Byzantines, Arabs, Normans, Swedish, French, Spanish, Albanian, Austrians and English.
Taste as many local delicacies as possible
I know I keep mentioning food, but the Mediterranean diet is one of the most healthy and variegated cuisines around. Food is like a religion in Italy, if it isn’t fresh, simple and delish Italians won’t eat it. From something simple like street food to a delicate gelato, fresh off the boat seafood, pizza sold by the metre or the best short black coffee you will ever drink, your taste buds will never forget the flavours of Italy.
Take home as much made in Italy as will fit in your luggage
There are many Italian artisans, small businesses and ancient crafts that exist only in Italy, helping keep them alive by buying good quality gifts from Italy. Everything from ceramics, jewellery, wine, olive oil, pasta, biscuits, artworks, stationery, leather goods, goldwork, textiles, coral, silverwork, and fashion. You will come across endless things to treasure and bring home.
Stay away from cheap and nasty Chinese stuff at markets, buy directly from small established boutiques for guaranteed quality, you might pay more but it will be worth it.
Be sure to check if you can bring in certain foodstuffs through the customs laws in your own country.
I know in Australia you can bring in anything that is cooked (ie: cakes and biscuits) or properly sealed like olive oil for individual consumption. But you will need to declare anything made out of wood or fresh foodstuffs to be inspected and possibly thrown out (things like cheeses, salami and Nutella will not be allowed to enter the country, unfortunately). If in doubt simply declare it when you arrive and worst-case scenario it will be taken away from you but if you get to keep it, bonus points to you!