I was in St. Thomas the last week of March on a press trip organized around the annual International Rolex Regatta. The welcome party at the St. Thomas Yacht Club welcomed not only the racers, but gusty winds accompanied by rainsqualls. By the next day, when we press people were out on a spectator boat watching the downwind start of the first race, it was threatening to blow the hair off the dog. Twenty-plus knots sustained, I learned later, gusting into the 30s. The system, the result of stationary highs, lasted through the next week and hit most of the Caribbean, and by April 10, when I picked up a NWS forecast, it was gone.
Of all the places in the world where you might charter, the Caribbean is the one where it pays to bet on the averages. The trade winds always come from the east, slightly north of east in winter, when 17 to 21 knots is normal, and south of east and lighter in late spring and summer. The "Christmas winds" of December and January are stronger, up to 25 to 30 knots.
Yes, said John Jacob, of CYOA Yacht Charters, in St. Thomas, we've had charterers asking for a refund because there was no wind or too much wind. Although this year's experience was unusual, you should be prepared for anything—just as you would if you were sailing at home.
Every CYOA client takes a pre-charter sail with a CYOA crew for both familiarization and evaluation. The crew, who keeps up with the latest weather developments, will put in as many reefs as he or she thinks will be needed before leaving the dock. Jacob says that monohull sailors especially are often unaware that cats need to be reefed very early and require judicious use of the traveler.
CYOA encourages charterers to phone in with any concerns. "The charter company is your resident expert," Jacob says. "That's what we're here for." If the wind is rising past your comfort zone, you can call for weather updates as well as suggestions for anchorages that will be sheltered in the day's conditions. And, if your crew is threatening mutiny, you can check in with the base and get an escort.
Unexpected weather conditions on a charter can be disappointing, but unless there's an actual hurricane nearby, it's rarely a reason to throw in the towel. Instead, use the towel to dry off—swim, go ashore, take an island tour, go for a hike—there's always plenty to do and much to enjoy.