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Lack of diversity? Venice/Florence/Rome

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I am planning to go with my family to Italy next April or May for 2 weeks... I don't have a lot of experience in travelling so from what I read the easiest would be to land by plane in Venice stay there for a few days, take the train to Florence stay there for a few days and then take the train to Rome stay for a few days and then leave by plane from Rome. I know that next year is still far away but I find it very fun to read a lot, make research, etc.

From everything that I've read, it's best to not have too many bases in too many cities, so I figure for 2 weeks I should limit things to 3 bases (Venice, Florence and Rome). Depending on the exact amount of days once the best plane deals is found, I'm thinking 3 to 4 days in Venice, 4 to 5 days in Florence and around 5 days in Rome.

I have a few questions and details:

- Hotels, B&B... How far ahead should we book? Do the best hotel disappear fast or will I find good deals in the months/weeks leading to the trip? Should I basically book everything as soon as possible?

- Train transportation... When should I buy the train tickets? Will there be places be available on the spot or should I reserve months in advance? And when I reserve, is it for a particular date? hour? etc, And is it easy to use the train between these cities with luggage or will it be packed with barely a seat available?.

- Dates to avoid... I read that during weekends the crowds are bigger... But what about transportation, should we avoid switching cities on particular days of the week? Do some things close on particular dates? Are there holidays to avoid? And for the months of April/May, what would be the best 2 week period according to you in terms of weather and less crowds? The earlier the better or for example would the end of May be similar to the beginning of April?

- I am not confortable in renting a car, is it best to stay in Florence for the Tuscany part of the trip? I am afraid that if we base ourselves in Venice/Florence/Rome, we will get tired of big cities, too many tourists, etc. Is it better to stay in a smaller town in Tuscany instead of Florence to kind of have a change of pace and add diversity, or are these 3 main Italian cities different enough?

- Do you think that day trips from Florence, Rome and Venice would give us a change of pace and diversity, or should we just sacrifice Florence for a smaller town?

- Any inexpensive hotels or B&B can you recommend for maybe 200$ per night or less, that are well situated at walking distance from the city centers and train/buses for day trips or switching cities? I am particularly attracted to hotels/b&bs that have a rooftop terrace with some nice views, that way during the day or at night, you can relax but still feel as if you are enjoying Italy as opposed to being inside a lobby or room...

Those are the first questions that come to mind, but I'm sure there will be many more... Thanks for taking the time to read...

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