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London, Paris, Milan, Como, Venice, Florence, Rome in one trip...too much?

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My wife and I will be making our first trip to Europe. We are planning on going for roughly 14-17 days. We have a friend in London so plan on beginning our trip there and spending 3 days, probably 2 nights. From there the plan was to travel via rail to Paris, spend 2 days, and then head to Milan. From Milan we thought we would visit the Lakes region and Bellagio for 2 days, head to Venice for 2 days, head to Florence for 2 days, and finish the trip in Rome.

Is this plan crazy or is it feasable? Are we trying to do way too much? We are thinking this may be the only time we have have the $$ to visit Europe and want to see as much as possible.

We would be taking trains and cabs did not plan on pre-booking any hotels either? We figured we would find a spot to rest our heads each night when we arrive in a new city? Is that a crazy idea as well?

How hard would be it be to rent a car while in Florence, explore the southern Tuscany region and then drive to Rome?

We plan on heading to Europe the last two weeks in June, into maybe the first week of July.

Thanks for the advice...it is much appreciated.

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