Go in January. Weather in January is the same as in February – still tropical and hot, but not too hot, like in Summer when it’s hard to do anything even remotely adventurous.

Good thing about January is that prices drop like there’s no tomorrow. Travelling during Christmas and New Year is extremely expensive. It’s a major rip off but most of all, unless you book well in advance, you won’t go anywhere. People are just that crazy about spending Christmas/New Year somewhere nice. That pushes prices sky high and makes for very limited availability (not only for Cuba, but basically anywhere in the world). But then as soon as early January comes, nobody travels anymore and prices go right down like you wouldn’t believe.

I wanted to spend Holyday season in Cuba two years ago. Prices were outrageous so I hesitated for a few days. I started looking in early November and it was just brutal. My few days hesitation drove prices even higher and most trips got sold out so my options narrowed significantly. After Cuba was all gone, I started looking at anywhere in the Caribbean. Again – outrageous prices and hardly any decent availability. Eventually I was forced to ditch the idea to go to the Caribbean and at least wanted a plane ticket for Memphis, TN to stay with a friend but even flights to the US were out of reach. Holiday season is a terrible time to travel unless you book months in advance.

I was forced to spend the holidays at home, but as soon as the New Year craze was over, return tickets to Cuba dropped to $49 return plus taxes. I have never stayed at a resort so I don’t know how much all inclusive stays were, but flying from Edmonton to Varadero for $49 return was amazing. And that was only a couple of weeks after same tickets were selling for $1600. So I was unhappy cause I had to spend the holidays in Edmonton, but I got the same trip for ridiculously lower price just a couple of weeks later.

People are too focused on travelling during the holidays and then when January comes, there’s no one to go. So prices go from sky high to near nothing overnight. Then they steadily grow until next peak around Easter, so going in February will still be cheap, but not January cheap. That’s when I would go.

February will be no different. Temperature will be more bearable, however when it gets windy in the evening, it could be cold enough to have to wear long sleeve jersey. Another disadvantage are short days as it gets dark at 6pm which puts a dumper on the rest of the day. You won’t find many locals on the beach either as they consider this time of year “too cold”. But value for money is incredible, it’s safely outside of the hurricane season and it’s not so scorching hot that you can’t even move, so you’ll be able to take part in fun activities.

January is your best bet. Unless money is not an issue. If that’s the case, go in April. The best time of year to go all around. I’m sure you’ve read about it already

Mark