We were given a lot of travel tips from friends for our Italy trip last year and I thought I'd pass them on along with some of our experiences. You may also want to purchase a Rick Steves Guidebook. He has invaluable information.
Luggage: Luggage dimensions and weight restrictions are constantly changing so be sure to check with the airlines before you travel. Some of the older luggage is heavy so it may be advantageous to look for a newer suitcase. (Look for sales or at Ross or Marshalls - they often have good deals) If you're also taking a bus tour, check with the tour company. We went with Trafalgar Tours and they don't allow wheels on carry on luggage, nor the same size as accepted by the airlines. There are only small overhead shelves on the coach and no room for large luggage. (I took a backpack).
To measure a suitcase, add together the height, depth and width.
If you have bulky items consider using space bags that can be rolled to get all the air out.
If you're travelling with a friend, consider exchanging one set of clothes in case one of the cases gets misplaced.
Water: Long flights can leave you dehydrated and you can't take bottled water through the security gates. Take an empty bottle or container and fill up at the water fountain just before you board. Use this around Italy too. There are usually water spigots in the piazzas and they seem to be safe to drink (I had no problems). At 1 - 1.50 euros for a bottle of water it can add up, but there are plenty of places to purchase water if you prefer to pay for it. This is also a good way to use their restroom. Tell them you want to buy water (or anything else you want) but ask if you may use their restroom first. (Often they will tell you they don't have one if you don't purchase something.) We timed our daily gelato purchases with restroom breaks.
Money: Let your credit card company know you will be travelling abroad and ask if there are any transaction fees. Discover doesn't currently add transaction fees, but is only accepted in places that take Diner's Club. I found very few places to use it. When making a purchase, make sure the transaction is processed in the currency of the country you are visiting. It's less expensive for it to be converted by your credit card company. Your bank may also exchange currency for you before you go. Wells Fargo will exchange foreign currency for a fee (approx. $7.50 per transaction). The fee may be waived if you have an account with them.
Also keep track of phone numbers for your card companies in case of theft.
Cheat Sheet: Make yourself a small wallet sized sheet of paper with currency conversions on one side so you can judge the cost of things. (Perhaps in $10 increments). On the other side put translations for words you might need i.e. Where is? How much does it cost? Where is the bus stop for ____? Also you will need to know a few numbers when haggling price (especially in markets). Or keep a small notepad and pen to write down what you are willing to pay.
Plan places you want to see: We had limited time in Rome and after listening to suggestions from friends, we planned out a walking tour on Google Maps which gave us directions, a map and number of minutes walking between sites.
People may stop you and ask you to sign a petition. Do not sign anything. They will use your signature for criminal purposes.
Also, do not give anyone your passport or documents unless you are sure they are officials. Some criminals show police identification but are wearing plain clothes and might ask for your passport or other documents. It's a scam.
U. S. Customs: Check on what is allowed to bring back to the U.S. Alcohol is limited and also meat products and other plant based items. More info. for U.S. residents here. You will be given a form to complete before you land in the U.S. Copy of the form can be found here.
I didn't feel uncomfortable in any of the cities we visited in Italy, but did find the walking street vendors annoying. They are usually not out to steal anything, they just want you to buy, but they can be very persistent with scarves, jewelry and camera items. If you do buy from them, you will be swarmed with several more vendors. It's best to buy from stands or shops.
Mailing postcards - a lot of independent mailing companies have popped up and they have little boxes to "mail" postcards. These are usually located in shops. There are many problems with this. One is that if you buy stamps in Venice you can only mail them in Venice and even then they may not arrive at their destination (some of my postcards arrived at their destination but two months after I mailed them!). I noticed a different company and different colored boxes in Florence. Either buy stamps at the post office and mail them there or wait until you get home. There are lots of forums on the internet where people have complained that their postcards weren't delivered.
Restrooms: There are free public restrooms at gas stations along the highway and in most cities there are public places but you have to pay 1 - 1 1/2 euros at those. Don't expect to find toilet seats on them. And in some areas of Italy there is no toilet at all. They are like a shower stall with a drain and two raised tiles to put your feet on. They are considered more hygienic!