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There are two basic seasons in Grand Cayman which travelers should be aware of when planning their vacations. The winter season is the season when people might prefer to travel to Grand Cayman, because this is the time when the summer storms diminish and the likelihood of encountering hurricanes decreases considerably. The summer season runs from approximately May through October and is the rainy season on the island; hurricane season lasts from the beginning of June through the end of November. The winter season, starting at the end of the hurricane season, is the season which is least rainy and most enjoyable in terms of temperature, averaging approximately seventy five degrees on winter days. The end of winter, in April and May, is usually the driest time of the year. Updated weather information for Grand Cayman can be found online at http://www.weather.ky/
Certain parts of the island are more susceptible to strong winds during the winter and early spring. During those months, there is a higher likelihood of having a nor'easter blow for several days, and such storms (which often consist of strong winds with little or no rain) have the greatest effect on the north and east sides of the island. During such times, the beaches on the north and east can be quite unpleasant, due to the incessant wind and the large amount of debris being washed ashore. Of course, such times can be great for scavenger hunting along the beach to see what has washed up, but mostly one will find large quantities of seaweed and seagrass. During the winter and spring, the accomodations along 7-Mile Beach offer the greatest chance of having swimmable, calm water outside your door.
In terms of events in the area, May is the best time of year to visit Grand Cayman. This is because the Batabano Carnival ( http://www.caymancarnival.com) occurs in May. This carnival is a huge street fair, similar to Mardi Gras or Brazilian Carnaval, but it is more family-oriented than either of those famous annual events. Another enjoyable annual event is Pirates Week, a week of numerous events throughout the island. Pirates Week 2012 is November 8-17 with the main activity, the float parade and pirates invasion being held on November 10th.
See climateandweather.com for a detailed month-by-month guide to the climate and weather in the Cayman Islands, with advice on the best time to go and what's on each month.