Planning For A School Holiday Trip

My friend just introduces a website for me. She knows that I am going to plan a trip on coming school holiday. Although there are another 2 months to go, but I like to plan for a perfect trip. Therefore, I will try to get all the information and reservation done before 1 month of the trip. So that, I have enough time to make changes if needed.

However, the Easy To Book website that she recommended for hotels booking seem like doesn't need to book 2 months advance. There are so many hotels available to select, so I do not need to worry will not get hotels later. I think now the problem is where should I go for this trip? Should I book for the Rome Hotels or New York Hotels? I should bring my kids to visit Rome or New York?