Pack Smart

What to pack? Tough question. Your brain says “pack light” but your heart says “But I need all these”. Go with your brain, trust me.

Keep to the 2-bag rule. A suitcase and a carry-on bag is all you need.

Pack your suitcase with wrinkle-free clothes and basics like a pair of black slacks, a black skirt, a pair of jeans and dress shoes. I used to over pack and end up not wearing half the clothes I take. You can always launder.
Roll your clothing instead of folding them so they don’t have lines when you take them out.
Lock the suitcase with a TSA lock otherwise the airport security would break it open if they have to. And since these total strangers have the right to poke and riffle through your personal belongings, DO NOT pack anything valuable or sentimental in your suitcase.

Now, the carry-on bag.

Limit yourself to 20 pounds because you will be lugging it all over the airport.

To minimize security hassle, take only travel-size items in your toiletry bag. It is easier to pick up your regular shampoo, toothpaste, shaving cream and other essentials when you land.
Pack a change of clothes in the event the suitcase does not arrive when you do. This is also helpful if you are overnighting in one place and flying off to your final destination the next day.
When I stay at a place for a couple of days before boarding a cruise, the carry-on would contain all I need for the land stay so I don’t have to re-pack the suitcase.
Always pack a bottle of Aspirin or Tylenol. When that migraine hits, you don’t want to run around looking for relief.

What about your shopping and souvenirs?

Buy a cheap tote bag (you can always get it at a bazaar or flea market) and put all your purchases in there.
Breakables should be properly packed and go in your carry-on.
Get a TSA lock for the tote bag as well.
If you happen to buy valuable items like crystalware or heavier items, you can always have the shop ship it back to your home. Better safe than sorry.