Does anyone know if booking the trip through Tripmasters is good?
Leaving May 19th; Arr May 20th Venice 3 days
Verona 1 day
Florence 3 days
Rome 3 days
Positano/AC 4 days
Naples 1 night
Leave Naples June 5th

Tripmaster seemed good because I can book hotel and airfare but if anyone has better suggestions, it would be greatly appreciated. Would it be less expensive to book airfare and hotel individually?

Do it all separately yourself so you can pick exactly the hotels you want and either book with the hotel directly or through something like booking.com. Tell people here your budget and they can make hotel recs everywhere.

Look for flights and flight times on sites like farecompare, travelzoo, etc. There are a couple that a lot of people here use, just can't remember the names offhand. Then, book either with the airlines or a reputable booking site.

<Would it be less expensive to book airfare and hotel individually?>

You just have to do the research and compare pricing. I don't know what "tripmaster" is so can't really compare it to independent travel arrangements.

I would plan around what I could do on trains. They are very easy to use in Italy. Much easier than car rental & driving imo.

I don't like 1 days stays myself. Just seems a waste of time.

Thank you all for your help. I've got everything booked individually and got a great deal on airfare, too. But I'm really confused on what to do for the trains. Should I get a two week pass? And how do I do that? Do I just buy the tickets at the station once I know the schedule? I'm totally lost about the trains and having never travelled this way before, I'd really appreciate the input/help. Thanks everyone :-)

No, you do not want a pass for Italy. As I posted way back in this thread, you need to read the extensive info on European train travel at seat61.com.