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WHAT TO WEAR ( or what NOT to wear) IN ST. JOHN???

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Hello to all of you wonderful travelers,
My husband and I are celebrating our 25 th anniv.in St. John (Caneel Bay)in Aug. and now I am rethinking the check/carry on luggage thing since reading that San Juan loses luggage (we go thru there). So if I do carry on I will need to pack less. My questions to you experts are;
What do I need to pack? will we live in shorts and bathing suits? when we go out to eat at some of the nicer restaurants (like Asolare, ZoZo's , Stone Terrace..) what should we wear? will we need more than sandals and tennis shoes (you know us women and our shoes!!)? will I ever have a reason to wear capris? We have never been to Carib. so I'm just not sure how to pack, I know it seems weird to ask how to pack but you guys ALWAYS have the answers!! Thanks for any info. offered !!

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