Travel Packing Tip #1:
Before you even choose a piece of luggage, consider your destination FIRST, including your trip’s purpose, and what activities you are likely to be enjoying. My own carry-on bag is pictured below to the right  It's a nice strong American Tourister that EASILY fits in the overhead compartment, but any small bag will do. It works for me, because I don't bring along recreational toys like my tennis raquet. If I plan on hiking, I wear my hiking boots on the plane instead of trying to pack them.

Obviously, packing for a resort ski vacation is going to take a different strategy than packing for an island resort vacation (unless you're a diver!). Certainly, you will need to pack quite a bit heavier for the ski vacation or dive vacation.

And I just read a blog post where a woman was mentioning that she has difficulty travelling without checking luggage because she has dive gear (translate: heavy and bulky and expensive). While she could certainly purchase some shampoo or sunscreen at her destination, it is completely impractical for someone to expect her to rent dive gear if she already has her own and is an avid diver. Same thing about the ski vacation. Fair enough, and everyone understands that!

But, we still advocate packing as lightly as possible. Instead of paying the airline for 2 checked bags, can you get it down to 1 checked bag? Along with the dive gear or skis, can you wrap clothes around the gear? Pad out the case with the extra jacket or wetsuit? We're saying to try being creative. 

What kind of carry-on luggage might be best for your needs? It all depends. On our trips to the Islands (most notably St. Maarten/St. Martin), John's carry-on doubles as a small daypack. This is because we tend to walk over to more secluded beaches, and it's easier to carry water and towels and sunscreen in a daypack as we hike to the beach.

One person who commented on a blog over at "Cranky Flier's" site had some great ideas! He (or she) suggested that perhaps you could send things ahead via UPS, which in some cases might be less expensive than paying for checked bags. Another suggestion was that if you have to pay the fee, go ahead and fill the largest type of bag allowed with as much stuff as you could. The perfect example was to fill a ski bag with everything you need for your vacation - and even if your vacation is in a warm climate, who cares? Do you really care if you're seen with a ski bag in Cancun? If the airline regulations allow it as a checked bag, and you want to bring all your "stuff," then who cares?

Again, check your airline's rules and regulations on this before you choose what kind of bag you're going to bring.