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how does a mother pack lightly?

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I am trying a new experience our next trip.

Instead of packing everything and being prepared for anything. ie: medical kit, books, items to occupy the kids when travelling, nice evening dress (with matching shoes) 'just in case' my DH ever takes me out to a ritzy restaurant, comfortable shoes for bushwalking and beach attire (which means swimsuit and beach dress) and then I will pack things that I believe DH and DS would need that they haven't packed, extra clothes for DS, favouite toy or book for DS, good shoes (for the ritzy restaurant) for DH etc.

I am attempting to pack lighter but I still feel the need to be 'prepared for anything' that our trip might encounter,.......

your thoughts please, sure the clothing side I am able to cut down, just concerned about the endless possibilities and my apparent need to be prepared.

Could all the Mums in the Fodor world answer with their tips and tricks (and those who grew up with travel savvy parents or are one themselves reply too!)??

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