We will be flying in and out of Rome. I want to see classical highlights, my wife wants to see Tuscany and my 16 year old son wants to go to the beach. We will have 8 days. Itinerary suggestions would be most appreciated.
I'd spend at least 3 days in Rome - stay near the train station and you can walk anywhere (the only metro trip we took was to the Vatican to be able to get there early - we walked back. If you plan 2-3 days for Florence (side trip one day around smaller hill towns). If you have a car in Florence you can visit more hill towns - it is really pretty country (we traveled by bicycle - hilly). Eight days is a little tight to get to Cinque Terre, which is my choice for seaside (Vernazza has a small beach area). There may be places at the coast near Rome. Maybe someone else can address that option. You'll probably want to come back to Rome overnight before flying home - spending an evening by the Spanish Steps is great for people watching.
Perhaps staying at a Tuscan agriturismo with a pool will satisfy your beach-loving teenager. I did a lot of extensive research on them recently, and most seem to have them. Probably should book soon if you want to do this.