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One of the reasons why many people, especially those from Canada, and Northern Europe travel to Cuba is to escape from the cold winter weather they have at home.
People in Cuba say that Cuba is an everlasting summer and I agree with them. I cant claim about the weather in Cuba.
Cuba weather is typical from a country with a moderate subtropical climate. There are generally two well identified seasons in Cuba: rainy (May - October) and dry (November - April). Though rain could be quite heavy at times, I dont think it is a problem you have to worry about if you are planning to travel to Cuba for your next vacation. On average there are about 330 sunny days a year in Cuba, so if you decide to go there on vacations just check Cuba weather forecast. It is very unlikely that you decide on the other 35 rainy days left.
Cuba has an average temperature from about 21°C (69.8°F) in December, January and February to about 29°C (84.2°F) in June, July and August and the average annual relative humidity in the island is 78°C. January February are generally the coldest months, though you usually have only two or three days cold. 
The weather in Cuba is perfect this time of the year. It is usually hotter in July August about 30 -34°C and no matter the season it is always about 3 4 °C hotter in the east of the island. In the evenings, it usually gets cooler, but not that much; a light sweater is perfect in a January or February Cuba evening.
Hurricane season lasts from June to November, but they are more common in Cuba in September and October. This weather in Cuba could bring flooding and winds of up to 250km per hour. However, not every year a serious hurricane affects Cuba and though it might damage economy and particularly housing, it doesn’t represent a risk for life because the country and especially hotels are very well prepared and organized for these climatic conditions
You can check http://www.cubahurricanes.org/ for more information on hurricanes in Cuba.
If you ask Cubans, they will probably tell you that the best months in Cuba are from May to September, because the weather is hotter and it is the time when most Cubans go to the beach. I would say the best time for tourists to travel to Cuba is from November to May. Temperature in these months is about 25°C, it hardly ever rains and average water temperature is over 25°C. Some friends of mine have visited the island on August, but you may find it very hot though, it all depends on how you feel about it.
If you have decided to travel to Cuba for your next vacation, Check our Cuba yearly weather page and make a decision about when the best time to travel to Cuba is.
When you visit Cuba you will realize that there is no much variation in terms of weather from one part of the island to another one
You can also check Cuba Weather Forecast in our site or consult the site of Cuba Metheorological Institute for an update on Cuba weather forecast or more detailed information on Cuba weather. Here is a link: http://www.insmet.cu/ and if you still have any question, just ask, I will be happy to answer.