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Capri, Italy
Capri is one of those cliffside towns that are so popular that you can't help but spot it over and over again on your Instagram feed throughout summer. If you prefer to hang out with a more thinned-out crowd, wait until September when peak tourist season ends and the hotels start clearing out. That way those picturesque beaches will feel a little less claustrophobic.

And don't worry: the weather here sits in the '80s during September, so you can still wear your cute dresses and go swimming.
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