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Usually the first step after deciding that you’re going to take an Italy vacation is deciding where, exactly, you’re going to go in Italy. Sure, there are big and famous cities and regions that everyone knows and that everyone visits (or at least what seems like everyone when you’re fighting the crowds), but there are quite literally hundreds (if not thousands) of great places in Italy to visit. I’d like to think that eventually I’ll get around to covering all of them on WhyGo Italy, but in the meantime, here are the places that I have written about already.

  • Rome – Italy’s capital, Rome is undeniably one of the country’s most popular tourist destinations, and with good reason. The city has both ancient monuments and modern attractions, and although it’s not exactly a low-key entry point to Italy, it’ll certainly get you into the Italian spirit of things quickly. I’ve written up a handy listing of what to do in Rome, plus a guide to Vatican City.
  • Venice – Venice is one of Italy’s most romantic cities, but it’s so perpetually over-crowded that you’ve sometimes got to make an effort to let Venice overcome you with love. Don’t worry, though, because I’ve got an abiding love for this city and I’ll help you find romantic Venice. I’ve got a list of what to do in Venice, too.
  • Florence – Though it can be called a must-see city for art lovers, Florence is more than that. It’s a gorgeous city with great food and fabulous leather markets, not to mention lots of Italian language schools (which is why you’ll always find the city full of students). Oh, and the art is world class, too. It’s been said that even in a week-long visit to Florence you still wouldn’t see all of the city’s famous art. That might be true, but I wouldn’t mind giving it a try. You can read more about what to do in Florence right here.
  • Milan – While most travelers skip Milan, it’s also a common entry point through its airport. And although it’s not the quintessential Italian city in terms of Medieval squares and Renaissance art galleries, it’s most definitely an Italian city. It’s home to the country’s world-renowned fashion industry, and is Italy’s banking and business capital. But there are still plenty of interesting things to do in Milan, if you know where to look.
  • Pisa – Home to one of the country’s most iconic images, Pisa is (for many) a two-hour stop en route from one palce to another. But even if your only purpose in getting off the train in Pisa is to see the leaning tower of Pisa, you should at least be familiar with what you’re missing, right? Check out the list of what to do in Pisa and you might just decide to spend a full day, or even a night or two.
  • Siena – Siena is second only to Florence as Tuscany’s top tourist city, and as soon as you set foot inside the old city walls you’ll understand why. It’s beyond charming, and you actually feel like it’s looked just like this for hundreds of years – because it has. It’s popular with day-trippers, but I recommend staying at least one night so you can get a feel for the city when it’s quieter.
  • Naples – Naples is the capital of southern Italy, and is the birthplace of pizza. As far as I’m concerned, that’s enough reason to go all by itself, but there are plenty more reasons to spend time in this bustling city. It’s not for the faint of heart, but Naples is definitely a place that’ll stick with you.
  • Cinque Terre – The name “Cinque Terre” literally means “five lands,” and refers to the five tiny towns which make up this micro-region. While they used to be sleepy villages that survived on fishing and grape and olive cultivation, they’ve turned into one of the top tourist destinations in Italy. Gone are the days when you could just show up and find a room by talking to the guy at the local bar – but with a little advance planning, a stop in the Cinque Terre remains magical.
  • Tuscany – Tuscany is famous for its rolling hills dotted with cyprus spires and poppies, its spectacular wines and food, and its charming Medieval hilltop towns. There’s every reason in the world that this region should be one of the top tourist destinations in the country, and that was true long before Frances Mayes was even born.
  • Umbria – If you want to experience almost all of what you’d see in Tuscany without fighting the massive crowds, head for Umbria. It’s not exactly off the beaten path, and it’s getting more and more popular with tourists, but it lacks the major sights of Florence and the name recognition of Tuscany in general, so it’s still less visited than its famous neighbor region. Umbria is also known for its adventure sports fanatics, so if you’re itching to try hang-gliding in Italy it’s the place to go!
  • Lakes in Italy – The region in the North of Italy that’s known as Italy’s Lake District is famous with honeymooners and romantics of all ages, and the breathtaking beauty of the lakes could turn even the hardest-hearted brute into a softie. The most popular lakes are Lake Como and Lake Maggiore, but the other lakes in the area are also worth visiting.
  • Amalfi Coast – This popular stretch of the Italian coast is just as gorgeous in real life as it is in the pictures, if not more so. The Amalfi Coast is one adorable and picturesque town after another, any one of which makes an ideal base for exploring the others. Positano is probably the best known (and therefore most crowded), but most of the towns are quite full with vacationers in the summer months so you’ll want to book well in advance to make sure you’ve got a room.
  • Southern Italy – While most first-time tourists in Italy stick to the cities in the North, they’re only getting half the picture. The further South you go in Italy, the more intense things get – both the good and the bad – which is part of what inspires such strong opinions of the area on both sides. But don’t listen to the arguments, go check out southern Italy for yourself and see what you think.