I was recently confronted with the not-unpleasant conundrum of how to make the best use of a one-week charter in a place (a) I’d never sailed before, (b) I am unlikely to return to, and (c) that is too big to sail and see it all in a week. What I consider to be “best use” involves a pleasant amount of sailing (but not dawn to dusk) and a reasonable amount of time to see the sights ashore and sample the local cuisine. It took a while for the penny to drop, and then I booked a one-way charter.
This wouldn’t have been necessary in, say, the British Virgin Islands, whose exemplary geographic layout permits what amounts to a circumnavigation of Tortola in the course of an easy week, with plenty of time for activities other than sailing. It could come in handy, however, in a strongly linear area like Belize, which has distinct cruising grounds in the north (out of San Pedro) and the south (from Palencia), either of which could keep you well occupied for a week. But you can have it all. For example, TMM Yacht Charters (www.sailtmm.com) offers one-way charters from both its bases, but suggests that starting in San Pedro and dropping off in Palencia, to the south, will keep you out of the occasional winter northers.
Another reason to consider a one-way charter is to sail when you want to sail while not having to deal with the anticipated seasonal weather conditions. One such is the strong northerly meltemi wind that affects the Aegean Sea and is a force to be reckoned with. If you want to cruise in Greece, in the summer anyway, one strategy is to charter in the Ionian Sea or the Saronic Gulf and skip the Aegean; another is to do a one-way charter from north to south and let the delivery crew take the wind on the nose on the way home.
The entire Caribbean is affected by the stronger “Christmas winds” of winter; they’re still trade winds, but at this time of year they blow from north of east. You can get bashed sailing south to north, but you'll get a free ride sailing north to south and will probably have a happier crew, particularly if you're chartering in the Windward Islands.
Some charter companies state that they offer one-way charters; a Google search for “one-way charters” turned up several. Or you may be able to persuade a company to arrange one for you. Money will, of course, change hands, but consider the magic trick of changing the sailing conditions or making one week seem like two.