You can sail to the Caribbean year-round, but the best time to go is when it's coldest in the Northern Hemisphere. Not only is the warm Caribbean climate a welcome respite from bad weather, but December through April are the driest months in the islands as well.
The cheapest times to cruise are typically in the late summer and autumn because of hurricane season, but you can often find patches of bargain sailings, especially during the early weeks of December and in the spring. The timing of spring discounts isn't always consistent, so it's best to keep an eye out and book when you see a low rate. If you dislike crowds or large numbers of children, avoid sailing late June through August or during school break times (late December, early January and March through mid-April). 

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