Look Into Transportation Passes
Do some research about where you're going and how long you're staying to determine whether or not a transportation pass might benefit you. In certain cities it is extremely beneficial and cost effective. Like in Venice, for example, the rates for water buses and taxis are outrageous if you don't have some form of a transportation pass. Even if you are only there for a couple of days, it could save you hundreds. If you are under the age of 29 then you qualify for the Rolling Venice Card which is a 3-Day tourist pass for 28 Euros (about $30 dollars) that includes unlimited use of all local public transport.
Be Wary of Lunch Hour and Mondays
This is a big one for first time Italy or Europe travelers. Always check the hours of a business before organizing two ferries and a bus route to get to your destination (oops). BEWARE THE ITALIAN "RIPOSO". This mid-day tradition closing of various businesses and sometimes even restaurants varies from city to city and business to business so it's always better to double check. It can run anyway from a half hour to a couple of hours usually between noon and four in the afternoon.
Another little known nugget of knowledge is that a large portion of business and restaurants (usually not in major touristy areas, but still occurs in places like Burano and Montalpulciano) are closed on Mondays. I found this out the hard way after making my way all the way to Burano from Murano only to find the historic lace shop I wanted to visit (along with several other businesses) was closed. My suggestion? Spend Mondays exploring architecture and beaches and maybe even hit up a local grocer in the morning and pack a picnic for the day. Some of my best days in Italy were spent stocking up on fresh meats, cheeses, wines, breads and fruit in the morning and spending the whole day driving around stopping here and there, taking in Italy's beauty.
You're Supposed To Get Lost
Yes, of course visit all of the famous shops that you've heard so much about or seen 100 times on Pinterest. But take some time to just get lost. I had a list of places that I had to go while I was in Italy, but my most memorable experiences were getting lost in the alleys and finding a restaurant with pizza that changed my life. Or hitting a dead end that brought me to the canal, but being able to watch a woman across the way singing to herself and hanging clothes up to dry. It's the getting lost and letting the city just swallow you up that's going to create the most lasting memories and the biggest impact.
Know Your Basics
I feel like a lot of Americans just assume that in most major cities (Venice, Rome, etc) throughout Italy, that a large majority of people will speak English. Sure some do, a lot of the younger generations. But a large majority DO NOT. It's beneficial and polite to know your basics. Even if you're not good at it, even putting in the effort makes people a lot more apt to help you or put in the effort to understand you. A simple "please", "thank you", or even "help" while holding a map can do wonders. And for you're benefit I've put together a cheat sheet for the basics you must know before traveling to Italy. Just click the image below to download.
Yes, You Can Drink The Water
And I'm not just talking about faucet water here folks, there are various public water fountains all over Italy that are perfectly safe and acceptable for the public to use. And on a hot day, when you've been walking for hours and a bottle of water is 3 Euros, you will be grateful for these fountains. We kept water bottles on us and then just filled them whenever we came across a fountain. And not only useful, they're usually beautiful as well.
When In Tuscany? Rent A Car
I'm not usually a car rental advocate because I feel like it's a waste of money. But when it comes to Tuscany it is definitely worth it. Sure, there are tours that go all over Tuscany but to be honest they're just as expensive if not more expensive than a rental car and don't give you the freedom to get off the beaten path. Rent a car, pick some villages and cities you want to hit, and make your own path! We knew we had to Montalcino, Montalpulciano and Montecatini Val di Cecina. But after that, we just drove wherever the wind decided to figuratively take us. If we saw a random hot spring in the mountains? Stopped. A secluded tree lined country road? Drove it. I can't recommend enough. Plus it makes the whole packing a picnic option a lot more feasible.