Single room in a hotel for a party of 4 if we check out in the evening?

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It would really depend on the hotel, and their terms and conditions. More than likely, you'll probably be charged for a full night as the hotel will find it hard to sell the room once you all depart.

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Milano Centrale station has a [left luggage office(http://www.milanocentrale.it/en/service/detail/left-luggage1); for 9 hours the fee is €7.80. There are of course toilets (with a €1 fee), but unfortunately no shower. It seems that there is a wifi hotspot too, I can't find any information as to whether it's free.

While there are hotels in Milan with day rooms, you'd have to vacate the room by 18:00 at the latest. It doesn't seem worthwhile unless you really want to sleep.

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