Travel packing is the same-anyone who says that you can travel for 2 weeks out of a small carry-on while snorkeling, skiing and attending a fancy ball is lying. But what you can do is choose! Usually between time/effort and money. You can travel for 2 weeks out of a small carry-on and do all those things if you are willing to pay to rent all the specialized equipment needed-this is the money option. Or you can pack all your own equipment and check 3 suitcases-this is the effort option. Or you can choose a beach vacation where all you need is a swimsuit and a cover-up, which fits in a small carry-on.
So how do you start? Be honest with yourself. What do you really value? If you really really really want to snorkel and ski and dance, then suck it up and decide if you want the money or the effort option. If you want to travel light, don't plan a complicated vacation.
Not sure what is important? Think about what stresses you out-and figure out strategies around that. I traveled around Europe for 2 weeks with a GIANT backpack that had everything I could possibly need. When I didn't use half of it and realized just how heavy it got after an hour of walking on old world cobbles it changed my packing strategy forever.
The black bag (MEI) is an internal frame backpack and has a day pack that zips to the outside. It was my original two weeks bag, now I use it for camping. These days the orange bag (Nautica) or yellow bag (North Face) is more than enough for one person for two weeks, both bags for two people. Steve Jobs book for scale :)
Now, communicate with your other travelers about what you need and how you plan to travel. Okay, this goes for ALL aspects of travel, and well, life in general. If you have mismatched styles, figure out what you cannot give up and how to accomodate each other.
Actual packing light tips
You can buy almost everything you are consider bringing. If you are on the fence, think through the scenario where you leave it home and then buy it on vacation. Is it a nice souvenir or an annoying time sink? I have large feet so I will have a hard time buying shoes in Asia or Italy. Everyone sells toiletries and it is fun to try Japanese conditioner.
Make items do double duty-I have a beach wrap/sarong thingy that I use as a shawl, a scarf, and a head wrap instead of bringing them separately.
Shoes are the heaviest items, minimize the number you bring. Sure it is NICE to have all your shoes at your disposal, but is it really necessary? Wear the heaviest ones on the plane.
Reconsider the definition of clean. During the work week I wear different clothes every day. On vacation, I bring one outer layer, 2-3 shirts, 2-3jeans/skirts and the right amount of underwear. It is okay to wear stuff more than once.
Consider doing laundry on your vacation. Many hotels have laundry facilities and in a foreign country everything is an adventure. I personally consider it a waste of time on vacation and would rather wear the same outfit 5 days in a row. The exception is underwear. Even there, if you want to go to the extreme bring 2 pair of something like Ex Officio underwear and clean one each night. Think it through for yourself, what will make your life easier?
Yeah new underwear!
Can you throw something out near the end of your trip? I went on a fall trip wearing an old coat and threw it away at the very end to make space for souvenirs. Do this in an environmentally responsible way-don't burden the Galapagos trash with your ratty swimsuit, but Miami? If you can't do without your brand of toothpaste, can you bring along just enough to last you the trip?
Can't pack light? Consider more car trips where you can stuff the trunk full. Or minimize the number of hotel changes. It is not so bad to get a cab to and from a hotel with a bunch of stuff. What is hard is the awkward time in between hotels or on the airport to subway to street transition. There is no shame in this-vacation is supposed to be relaxing.
Even the small things are important to think about. I have a 10-minute toothbrush routine that involves many Things. I like my teeth to not have a grungy feel. But I have discovered that I can replace the electric toothbrush with the rubber scraper thing on camping trips.
When you have a lot of transportation changes, no more than two bags per person-they become unwieldy when going from airport to subway to street. Even better if one of them is a backpack.
Think you have done a good job paring it down? Actually pack it and use your local public transportation for a 2-3 hour round trip.
What do I always travel with?
Eyeshades and earplugs. I am cranky without sleep and these are hard to buy except at the airport.