Traveling to Tuscany

Whereabouts in Tuscany does the wedding take place? As Florence is in Tuscany, and is incredible, that is probably your best choice of city to explore. It deserves at least a four-night stay. As for traveling north, trains are the best choice.

Is 7 days the total of your trip? Will you need a rental car to reach the wedding location?

First check flights; if you can find an "open jaw" deal into Florence and out of Milan, you can accomplish your goal easiest. The high-speed trains are by far the easiest way to travel; two hours from Florence to Milan, but those rise in price daily, especially for the most popular schedules, and the schedule may not be released yet for June.

If you have only 7 days, I'm not sure how many other towns you can squeeze in. Florence is awesome, and there are many train-accessible small towns nearby (Lucca, Siena, Pisa, Volterra, etc.) for a day trip. I haven't been to Milan or Como yet.

If you need to drive to the wedding, be sure to swing by AAA (before you leave the US) for an International Driver's License. Driving anywhere near cities is intense, so I'd skip it unless you're very experienced with EU driving.

Once you know where you'll be, and if you share your tastes for hotel/food (simple/fancy/local?), then more recommendations can follow. Rick's books are great for these questions.

I'm solo. Staying at a hostel in Florence (I use hostelworld) for 3 days, then renting a car from Budget and exploring places around Siena, then return to Florence. You could keep the car and go to Lake Como and then return it to Florence. Just don't use it in the city.

Is the wedding at Lake Como? Have you been to Italy before?

We really need a better idea of the rest of the trip before we can offer helpful information.