In the caribbean this winter, you're not going to need much more than a swimsuit. Sure, it can be scary waking up each day thousands of miles from your wardrobe. But anyone who checks more than her golf clubs en route to Vieques or Nevis has a problem. Instead, stick with a single, compact, soft-sided bag, and let it accomplish what willpower can't--that is, reduce the mountain of sweatshirts, chinos, and extra shoes that you "might need" to a chic mix-and-match ensemble of beachy essentials. Our favorite carry-ons are bright and sporty, clearly more pleasure than business. You wouldn't bring them on a junket with your boss, but you probably wouldn't bring that string bikini either.
Utility Canvas is the go-to source for sharp, inexpensive overnight bags in sturdy fabrics and eye-catching colors. Try a splashy, compact portmanteau ($68, shown) or a larger one in your favorite neutral ($85).
Utility Canvas, 146 Sullivan Street (212-673-2203).
Jack Spade, from the makers of those ubiquitous nylon totes, has plenty of street-chic satchels that let guys in on the trend. The "weekend" one holds twice what you'll need for a couple days' diving off Grand Cayman ($312).
Kate Spade, 454 Broome Street (212-274-1991).
Louis Vuitton's latest crop of luggage is a lot less cumbersome than its prized steamer trunk, but the oversize, sailor-style sling pack ($780) packs almost as much, and the shoe compartment underneath can hold up to five pairs of sandals.
Louis Vuitton, 116 Greene Street (212-274-9090).
Gucci's new printed carry-on ($770) won't hold much more than a few slinky slip dresses and a stash of bikini bottoms--but for the St. Barts crowd, that ought to be enough.
Gucci, 10 West 57th Street (212-826-2600).
T. Anthony, the pack rat's fave for trunks and hatboxes, has duffels that are a tad easier to get onto a seaplane. For an "I ride horses even when I'm not on vacation" look, fill the "Polo" bag ($395) with enough linen and pearls for a week in Bermuda.
T. Anthony, 445 Park Avenue, at 56th Street (212-750-9797).
Prada's metallic-silver cinch-top duffel ($350) looks like it could radio for help if you were lost in the Antilles, but don't be fooled--the tough-looking shell is actually so soft and supple you'd be happy to share your berth with it.
Prada, 116 Wooster Street (212-925-2221).