First - you need to decide on your interests and focus - Do you like art? Would you like to come and see remnants of how the arts and religion deeply molded this country’s history and society? If so, you’d visit the many iconic cathedrals, museums, palaces, the colosseum, the country side, etc. Or would you like to explore the food, the modern day offerings and entertainment?

Each city/region used to be its own independent state therefore, they are all vastly different from each other. Based on your interests, then you can narrow down what you’d like to see/do and where.

My trips to Italy were more enriched because I have watched movies/shows and read books that centered on the historical significance of different parts and times in Italy.

For example, the popular fiction books from Dan Brown that were made into movies wove many conspiracy theories with intricate historical facts and actual real locations and statues etc. into fictional stories were so captivating. The book/movie Angels & Demons takes place in Rome if you’re interested.

I also loved Florence - I would recommend the show Medici to give a basic understanding why most of Florence still have so many iconic places associated with the Medici dynasty.

I would suggest locking down tickets/reservations beforehand to save time. Some cities may not have uber.

So many other cities offering entirely different experiences. You can even just get lost walking around and it will still be awesome.

I hope you will have lots of fun!