Charter Vacation: Planning That Winter Sailing Escape

How to avoid potential pitfalls during your charter escape from winter

As we turn the calendar to September and the unofficial start of fall, those of us who never want to go too long without a sailing (and warm weather) fix naturally start thinking about a winter charter in the lesser latitudes. Having escaped to the tropics myself many times, I can confirm that there are few feelings more satisfying than being anchored off a white sand beach while storms howl at home. Yet, winter charters require careful consideration, because like any other sojourn far from home, there are potential pitfalls that can be avoided, or at least mitigated, with some careful planning.

chartering destination
Charter vacation pitfalls can be avoided with careful consideration and planning.













Price point

The most obvious drawback of a winter charter becomes apparent as soon as you start navigating those enticing websites: the cost. Winter is high season, when rates—especially at Christmas and New Year—can be a multiple of low season rates. But if you don’t have to get away in the middle of February, and can either schedule before the worst of the cold (remember: they don’t celebrate Thanksgiving in the Caribbean), or afterward, you might still get the benefit of an escape but at a more tolerable price.

Weather patterns

Although many of us perceive the islands to be a year-round tropical paradise, they are not immune to winter conditions. The Bahamas, for example, can fall prey to cold fronts barreling off the U.S. coast, making winds boisterous and temperatures cold. The Virgin Islands can suffer from “Christmas winds,” when isobars close in on each other and treat visitors to 25-30 knot winds. This weather pattern can extend into February and even March.

We once spent an entire British Virgin Islands charter fighting these winds, spending sleepless nights on mooring balls while our boat sailed from side to side. Moving to a slip didn’t provide much respite, as the noise of slapping waves, clanging rigging, and squealing fenders kept us awake. During our week, some charterers were so intimidated by the winds that they only daysailed and stayed at the base every night.

The same week, winter storms up north helped produce a “ground swell,” making most north and west facing anchorages untenable. The seas at Smuggler’s Cove on Tortola were so high that half of the beach was under water. And sailing on to, or staying in, Cane Garden Bay à la Jimmy Buffett was a recipe for misery.

Unfortunately, these weather and sea patterns are the luck of the draw. The further south you go, or the earlier or later in the season, the better your odds. Or, you can do just as we did and make the best of a less-than-perfect situation; there are certainly compensations, and nothing a Painkiller at the Soggy Dollar Bar in Jost Van Dyke can’t fix.

Getting there

The winter drawback I’ve most often experienced is, ironically, the weather I’d been trying to escape. It’s vexing to be late reaching your destination due to flights delayed or cancelled by snow, though less so to be stuck not being able to get home because your home airport is closed. I’ve spent extra nights in Miami, FL, San Juan, PR, and Dallas, TX, trying to get down island, or home, making those winter storms more memorable (and costly). I often buy trip interruption insurance to cover those unexpected expenses, and sometimes build in a little cushion in my travel schedule so as not to miss a second of long-awaited sunshine. I avoid scheduling connecting flights through bad-weather airports (O’Hare, Newark), but there’s not much that can be done if it’s your local airport that is the problem.

So worth it

On balance, however, I’d rather “suffer” winter in the islands than at home, even if it’s not perfect.

by Eva Hill

This article was first published in the November 2015 issue of Spinsheet

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