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You can fit everything you need in one carry on bag. Here's how:

Clothing

Choose clothing with thin materials that you can layer. For a weeklong vacation this is what I pack:

• 5 thin shirts. That way you have a new blouse for 5 days and you will wash out your 2 favorites and wear them twice.
• 3 pairs of underwear. Wash them out at night and they will be dry in the morning.
• 2 pairs of thin slacks--the one you're wearing on the plane and an extra pair.
• 2 pairs of capris for if it is hot.
• 2 pairs of socks, the ones you will wear on the plane and an extra pair. 
• one warm sweater/jacket that you will carry on your arm to the plane so that it doesn't fill up your suitcase and you have it in case the air conditioning on the plane is too much. If you don't need it on the plane, throw it up with the carryon. There is always room to stuff a sweater up there.
• one pair of semi-dressy but comfortable loafers that you wear on the plane and will do just fine for going out to dinner at night.
• pack one pair of comfortable flat sandals that you can wear most of the time if it's hot.
• one pair of pajamas.
• a swim suit if there is a pool in the hotel
• a pashmina or 2 (a warm scarf) that you can use over your shoulders at night or to dress up clothing

Toiletries

• Soap, shampoo and often conditioner plus a hairdryer are provided by most hotels so don't pack this
• pack makeup in your purse in case you are separated from your bag
• your most recent eyeglass prescription in case your glasses break while on vacation. If you have time you can get a new pair made. And/or pack your old pair of glasses (might be a bit blurry but better than nothing).
• Prescription medication

Sundries

(keep to the bare minimum)

• a mini umbrella
• either a roll of duct tape or a bungie cord in case your suitcase zipper breaks (it happens)

Art Supplies

DO NOT BRING EVERY ART SUPPLY YOU OWN BECAUSE YOU CANNOT HAPPILY LUG IT AROUND ALL DAY WITH YOU. Pack light. Only bring what the Instructor has listed and no more.

Here's a quick video called Packing Hacks for Urban Sketchers 

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