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Can a gal grow to love Florence if she felt iffy in the past?

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I am traveling to Italy for two weeks next May (early, but after the May holiday) with my sister (she's never been) and planning on introducing her to Florence, Tuscany or Umbria, and then Rome. We are both serious art and history people. There is a full plate of places I would like to visit in Florence and I might use it as a base for a day trip to Lucca or Bologna.

I was in Florence 4 years ago in late June with my family as a day trip. We did the Accademia and Uffizi. It was so hot and crowded that we walked past the Duomo, across the Ponte Vecchio, and up to Piazza Michelangelo--could not wait to get back to the calm and coolness of our farmhouse apartment near San Gimi and its pool.

This time, I am thinking of staying in the Oltrarno area in an apt for 4 or 5 nights. I have loved all the places in Italy that I overnighted in (Venice, Bologna, Rome, hill towns) and have been cooler to some places we daytripped to (Milan, Pisa), So I think it may be a day tripper vs. longer stay problem.

Now the million dollar questions: Will the crowds be manageable? Is it likely to not be so stinking hot? Is it, like other towns, more enjoyable in the evening as the daytrippers leave? Is it possible that I will love Florence?

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