I learned my lesson the hard way. My family and I were going on a 10-day Mediterranean cruise. Breaking every rule in the book, we packed like carnivores at an all meat buffet. Our oversized bags included stuff for every possible scenario—except the one where the airline loses all of our checked luggage. Yep, 10 days, no luggage.
It was one of the best trips we’ve ever had. Rather than a cabin strewn with half-emptied luggage, mounds of toiletries and cascading piles of shoes, ours was neat and uncluttered.

How’d we do it? We had a couple of days in Rome which, as luck would have it, is probably one of the most expensive cities in the world to purchase normal stuff...(think $12 bucks for a pair of white tube socks). Even taking the train out to a distant shopping mall didn’t help much.

The first thing I did was contact our cruise line, Holland America. They said they had cocktail dresses and a tux we could use for our “fancy” nights. (I also learned something interesting—they rent these on the ship.) They graciously offered to comp these if our luggage didn’t show. They had a fascinating room of “lost & found” clothes. It was filled with stuff people left behind and never requested back. They said we could borrow anything from this room we needed. (This took care of PJs and sweaters/sweatshirts.) They also offered to do our laundry daily. (I got the feeling they were used to the lost luggage scenario.)
Being on a budget, I gave strict orders. Everyone could buy two bottoms and three shirts. Fortunately, I had the policy that everyone wear their “walking shoes” when they're flying. So, only one additional pair of shoes needed to be purchased . Some underwear, socks and minimal toiletries rounded out our "ensembles".
Not only was the clean room a benefit—the “what to wear” decision-making process in the morning was so simple. We basically rotated outfits…one on our bodies and one in for cleaning (we gave them to our cabin steward the evening before or first thing in the morning.) Our clean clothes were waiting on our bed each evening after a day of sightseeing. (This is another great tip I learned to make packing easier and lighter.)
Here are my 9 tips to Packing Light… (Learned from hard-earned experience).
1) Carry-on important stuff. Meds, money, IDs, favorite cosmetics, phone, iPods and cameras should always be in your carry on.

TIP: I learned this years ago from The Today Show.
Scan or Xerox all of your important documents including your passports, driver’s licenses, credit/debit cards (both sides), medical insurance info, itinerary and booking confirmation numbers, etc. Provide a hard copy or thumb drive to someone you implicitly trust (such as your mom). If your wallet or purse is stolen (along with some of these valuable items) you’ll be able to quickly replace or cancel them. This will save you a great deal of time and frustration when trying to track all this information down. 
TIP: Lost or stolen Passport? If it’s stolen, contact the local police so that you have a record of the crime. And then contact the local embassy or consulate to alert authorities that your passport or VISA are no longer in your possession. They will also help you obtain a replacement. Consular personnel at U.S. Embassies and Consulates abroad and in the U.S. are available 24 hours a day, 7 days a week, to provide emergency assistance to U.S. citizens.
2) Your suitcase. No matter how big the bag is, somehow most of us can fill it up. Your bag should never be larger than what you can manage easily by yourself (lugging through streets, trains, etc.) If you can manage to just take a carry-on, all the better. No worries about lost luggage.
3) Just your favorite stuff. We all want to pack that dress that looks great, but is a bit uncomfortable, so you rarely wear it. You’ll find that on vacation, you’ll lean toward your comfy clothes. Don’t pack something that you wouldn’t wear at home.
4) Check the weather. If it’s been 80 for the past month, don’t bring along cool weather clothes “just in case”. Pack for the appropriate weather If it tends to be rainy a lot, a trench coat is a good idea. Hot and sunny? Pack your favorite hat and cool, cotton clothes. Beaching it? Don’t forget a cover up and bathing suit.
5) Color Coordinate. Choose a color scheme and carry it through. Black is great because it doesn’t show dirt and is more forgiving on wrinkles. Mixing and matching will go a long way. White as a secondary color is always perfect. For example black shorts, black Capri’s, black skirt, black sweater or jacket, and a white skirt or Capri’s, white shirt…and then throw in a couple of various colored shirts and you’ve got several looks…there’s no need to pack
shorts, Capri’s and skirts in multi-colors…it’s likely you’ll end up just wearing the black anyway.
If you're packing for kids...keep it to what they know and like...jeans, khaki's, etc. And don't forget the backpacks...or you'll end up hauling all their stuff around!
6) Easy Maintenance. Don’t pack stuff that looks like you’ve slept in it when it comes out of your suitcase. Wrinkle-free clothes are the way to go. New breathable fabrics make low-maintenance clothes comfortable as well.
7) Take advantage of Laundry Services. If you’re like most of us, you’ve got your favorite item. Mine are a pair of these comfy black Capri’s that are perfect for either sightseeing or pairing with a nice shirt for dinner. These are a mainstay and always plan to wear them often when traveling. I just get them cleaned and pressed every couple of days.
8) Shoes, shoes and more shoes. You only need three types of shoes…walking (if you’re sightseeing), flats and heels (I often forgo the heels and opt for black flats that work at day or night). You can throw in flip flops if you’re beaching it.
9) Make a list. Somehow, putting it on paper will give you a better idea of how much you’re actually bringing. If you’re bringing more outfits than are physically possible to wear in the time frame you’re traveling…it’s way too much.
Packing lighter has many benefits. Now that the airlines charge for extra bags and weight, it’s fiscally sound to keep it light. You’ll also have space to bring back some of the keepsakes you’re likely to buy.
But perhaps the biggest benefit, in my experience, is that it keeps it simple. When I have tons of clothing, it simply takes much longer for everyone to get ready in the morning or evening. Just a couple of choices (for everyone traveling) will actually save you time in the long run....and give you more time for the fun stuff!