Cinque Terre is the name of an area consisting of five or six villages on the coast. To search for a train, use the name of one of the villages. I know Monterosso is one.

1) Yes, use that link for your schedules and purchases.
2) You probably don’t need to purchase tickets in advance for that time of year, but why not go ahead and have peace of mind? You may already know this, but Cinque Terre is not a single location, but a collection of five villages. When you look for tickets you should enter one of the five as your destination. A little info:
http://www.italylogu…

You’re moving around a lot. Your trip will feel like a whirlwind.

Wait till you arrive in Florence. Go to the station and they have self service ticket machines that will accept your credit card. The train times are (just an estimate, look for faster trains with less stops. Pisa also has self service machines. All machines can be used in English. The lines for the ticket office are usually very long. Florence to Pisa + 1 hour; Pisa to La Spezia 50mins,; La Spezia to Manarola 10mins. These trains are not crowded on your dates. TIP: When you arrive at your destination in Cinque Terre or visit one of the 5 villages by train, always look at the times for departures and write them down in a small notebok so you can enjoy the village for as long as possible and arrive at the station 5mins. before departure. Be sure to read the fine print. Many trains do NOT run every day. Be sure to call your bank and let them know you are traveling to Italy so they don’t shut down your C/C or ATM card since it is not your typical purchasing pattern.

i think yr plan is good but you will find more info in google about the destination and sight seeing advoid wasting time!
edited by moderator to remove advertising spam and link

I just returned from living in Florence and here are my answers:
If you have any questions, please feel free to ask!

1) For just travel inside Italy use …
Trenitalia’s english website has the cheapest fairs and most accurate schedule, keep in mind these other sites want to make a profit. Also if you need to go for example from Florence to Rome, you can take a florence to napoli train with a stop at Rome, and it will be the same time (1 hour 45 min roughly) but cheaper

2) We need to travel from Florence to Cinque Terra. Do I need to buy these tickets early in your opinion? Do the train booking websites have a list of the train station abbreviations, When I add cinque terre as the destination city from florence it doesn’t accept it?
I know it may sound touristy, but cinque terre on your own can be time consuming if you dont know what your doing. If your in Florence, go down Via Santa Maria (away from the ponte vecchio) and make a right on via lamberlesca and theres a tour company that does day tours to the cinque terre for 75 euro which includes transportation on a bus both ways plus tour and lunch at a wine farm. there are many places in florence that do this. Its the same price as round trip train ticket.

3) Should we just book all of our train rides now? We need them from Florence to Cinque Terre to Florence to Siena to Rome.
No, book at the station, the only train is the Friday train to Rome which you should book a day or two beforehand.

About the soccer game (I trained in Coverciano with the fiorentina team ) make sure you have ID to buy tickets and to enter the stadium, unlike US sporting events, each ticket has your name on it. If its a big game, buy the tickets in downtown florence at Piazza Replublica