Italy has a wide range of things to see and do. We spent 10 days road tripping through the country from Sorrento in the South, to Venice in the North with a quick stopover in Florence as well.
When to go: September-October, April-May; You'll get the best weather with the least amount of crowds.
Where to stay: Italy is home to some of the world's most beautiful cities. Personally, Florence was by far my favorite city with incredible architecture, excellent food, historic buildings, and wonderful people. Other options would be Milan, Rome, Venice, or the Amalfi Coast. The Amalfi coast has some seriously stunning views. Be sure to check out the 5 best (affordable) boutique hotels near Venice
Getting Around: Unless you are familiar with driving in Italy, I would highly recommend using their excellent public transportation. In our opinion, Italians are not the best of drivers and many street signs are taken as suggestions.
Things to see
Sorrento and the Amalfi coast - This area is absolutely breathtaking with villa dotted cliffs dropping sometimes 1000 feet into the Mediterranean sea. The drive is not easy - we actually scraped up our rental car here! (An Audi too OUCH!) There are plenty of options to take a private or group tour of the Amalfi coastline. Visit some of the quaint, picturesque towns along the way such as Positano and Amalfi.
Visit Pompeii - There is nothing like seeing a city that is almost 2000 years old and is well preserved. The ancient city is far greater than you could imagine and is still being excavated. Unlike us, you should come prepared! Make sure you have comfortable footwear, sunscreen, eat before you go into the city, and bring plenty of water. Go in the morning before the throngs of tourists arrive. There's a shitload of tourist traps just outside the entrance. Don't say I didn't warn you!
Take a boat tour to Capri - There are multiple tours offered of the Italian coast and we found the island of Capri to be one of the most beautiful places we have seen. While your out on the water, check out the Blue Grotto!
Get lost in Venice - Venice is not huge and you can see much of the ancient city within a day. In Venice, its best to leave the map and just explore. The main canals can be flooded with tourists and if you want to get the true vibe of the city, it is found wandering the small canals and checking out local shops and cafes. Wear good shoes!
Visit the many historic cities in Italy - Rome, Florence, Milan, the Vatican, there are so many historic places to see, ancient ruins to explore, and tons of wine and pasta to taste. We fell in love with the atmosphere of Florence and I look forward to spending more time there the next time we are in Europe!