As far as deciding when to go, again, much depends on personal circumstances and preferences. Not surprisingly, months designated as high season are usually the most desirable times to sail, not only for reasons of climate and weather in the charter area but also because of the weather back home.
In the Caribbean, for example, summer sailing is superb—the temperature doesn’t vary more than a few degrees from winter to summer. But most sailors want that dose of tropical sun, turquoise water, and balmy trades when the temperature at home is in the single digits and the boat’s laid up in the yard. For this reason, winter prices in the islands are higher than in the low season (summer) or fringe season (the period of time between high season and low season).
High, low, and fringe seasons vary according to locale, but if you’re on a tight budget, off-season or fringe-season sailing can save money; most companies offer substantial discounts or incentives in off-season months. In most areas, you can save from 10 percent to 60 percent.