Getting Started: Wear What You Don't Want to Pack
With almost all airlines charging an extra fee for checked baggage, travelers are trying harder than ever to stuff all they will need for a trip into a single carryon bag. That's hard to do when you need to pack parkas or ski gear, but luckily Caribbean travel demands mostly lightweight clothing that's relatively small and easy to pack.
The first thing you need to think about when packing light for a Caribbean trip is not what's in the bag, but what's going on your body. Always try to wear, not pack, your bulkiest items. No, this doesn't mean wearing five layers of clothes so you don't have to pack them! Rather, use common sense and dress for your Caribbean flight in whatever warmer clothes you plan to bring for cooler evening activities in the islands: a sweatshirt, light jacket, or sports jacket on top, and a pair of casual-but-neat or dressy long pants on bottom. Also wear the most substantial shoes you plan to pack, whether they be dress shoes, sneakers, etc.
For the purposes of this demonstration, I'm using a standard-sized rolling suitcase -- the size that you (usually) can carry onto the plane. Remember that most airlines allow you to carry on one piece of luggage and one smaller bag, such as a pocketbook, computer bag, etc., that can fit under the seat in front of you. If you're in a hurry to get to your Caribbean resort destination once you land (and who isn't?) it's always a good idea to carry your luggage on rather than checking it. Just be careful to follow the TSA rules regarding liquids when you do. Liquids like shampoos, mouthwash, etc., must be 3.4 ounces or less and be packed in a clear bag for inspection.
Getting Started: Roll 'Em!
You've probably heard about rolling your clothes when you pack. It's good advice: I have found that rolling not only saves some space but also helps prevent wrinkling. When packing my suitcase for a Caribbean trip, I always start with the biggest items first. For me, that usually means a pair or two of long, khaki or black pants, the kind that can be worn more than once, are appropriate for a casual night out, but also look good with a suit jacket and button-down shirt (no tie needed in the Caribbean!).
Shirts, Bathing Suits, and Sleepwear
Next in goes my shirts: For a week-long trip, I usually bring two dressier button-down shirts, perhaps three collared polo shirts, and four or five t-shirts. For women, this is when you should pack any dresses you plan to bring. Roll them and pack into the main body of the suitcase. Likewise, bathing suits: two is plenty for me, and it's good to pack a plastic bag for soggy suits on the way home. Finally, something to wear to bed is nice, such as comfortable lounge pants.
Socks, Belts and Underwear
OK, it's getting pretty full in there, but still plenty of room to stick in some socks and underwear, which are great for filling in small spaces around the bigger items. Ditto for a wrap, sarong or coverup for the beach. I usually try to bring at least one or two extra pairs of undergarments or socks ... because you just never know. Wearing a belt is just one more hassle when you pass through airport security, so I usually pack mine by wending it around the inside rim of the suitcase after all of my clothes are packed.
Most luggage includes a zippered or mesh pouch that is excellent for storing a pair or two of shoes. For a Caribbean trip, I typically pack a pair of sneakers and a pair of sandals or flip-flops, unless I'm planning on hiking (in which case I would wear my hiking boots and pack my dress shoes). I have found that I can usually squeeze two pairs of shoes into the zippered compartment, or one pair of shoes plus a toiletry bag.
OK, take a last look at your bag. Is it stuffed to the gills, or is there a little room left for that one must-have item you need to take along (curling iron, small hair dryer, etc.)? Or should you leave a little extra space for those inevitable Caribbean souvenirs you'll be bringing home?
Once you decide, close the bag. In all likelihood, you'll notice that the outside of your bag has a few extra pockets. I like to use one of these for my toiletry bag, because it not only saves space inside my bag but also prevents my clothes from getting sodden should one of the liquid bottle open or break during flight (not uncommon). Also, if airport security feels compelled to check your toiletry bag then they can get at it more easily and don't have to open your entire suitcase.
The Other Bag, and Miscellaneous Items
Voila! You've finished packing your luggage. Now, let's talk a bit about that "other" carryon bag you're allowed to bring on board.
As mentioned, the key consideration is whether this bag can fit under the seat in front of you on the plane; typically, that means a handbag, computer bag, small backpack or briefcase. I usually bring a computer bag for my laptop, but other travelers may find the backpack or handbag more practical and useful.
Besides the computer, I use this bag to hold most of my travel documents (besides my ticket, passport and wallet, which I keep in an inside pocket), iPod and headphones, sunglasses, a book or two, and perhaps an item or two that didn't quite fit in the suitcase -- an extra tube of suntan lotion, for example. If you don't have a computer, this bag is great for carrying your toiletries, and some travelers insist on packing an extra pair of underwear and socks here if they are checking their other luggage (again, because ... you just never know).
You're Ready to Go!
That's it: you're all packed and ready to hit the beach! Sure, you may have to wear a pair of pants and your dress shoes more than once on the trip, but at least you'll always have clean underwear, socks and shirts. If you feel compelled to bring an extra bathing suit, go ahead: they don't take up much room.
Of course, I'm writing this from a male perspective, so I recognize that women may wish to pack more in the way of toiletries and makeup. Usually, it's not a problem to find room for one or two extra items with this system. And believe me, it's so worthwhile to avoid the hassles of checking bags, lugging around extra suitcases, and the added insult of the airline charging you for the privilege!
One final hint: If you have space, pack an extra empty bag, preferably a backpack, if you have room. It's always helpful to have a day pack with you when you are heading to the beach or on an excursion, and you can also use this bag to pack any gifts, liquor, or other souvenirs you pick up in the islands. Even if that leaves you with three bags for the flight home, you can check one, put one in the overhead bin, put the third under the seat, and still avoid the excess baggage fee now being charged by most airlines.